Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
4.9 (1,436)
Key West 4 Seater EZGO Golf Cart Rental
Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...
3 hours and up Free Cancellation
4.9 (1,436)
$99
4.9 (1,436)
Key West 6 Seater EZGO Golf Cart Rental
Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...
3 hours and up Free Cancellation
4.9 (1,436)
from
$180
$180
4.9 (1,436)
Key West 8 Seater EZGO Golf Cart Rental
In Key West for a wedding or other family event? Got a large group of cruise ship friends who want to see all of the...
3 hours and up Free Cancellation
4.9 (1,436)
from
$210
$210
4.9 (75)
Key West 1 Seater Scooter Rental
Zoom along solo and park with ease at every stop on a Yamaha Vino 1-seater scooter. This classic Key West scooter rental sports a quiet,...
3 hours and up Free Cancellation
4.9 (75)
from
$45
$45
4.9 (75)
Key West 2 Seater Scooter Rental
For a Key West scooter rental that offers the fun of two-passenger touring, the Yamaha Zuma 2-seater is a great way to explore the island....
3 hours and up Free Cancellation
4.9 (75)
from
$55
$55
4.9 (1,168)
Key West 4 Seater Electric Car Rental
Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...
3 hours and up Free Cancellation
4.9 (1,168)
$99
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
4.9 (1,168)
Key West 6 Seater Electric Car Rental
Our 6-seater GEM electric cars beat any regular rental car hands down when it comes to zipping around Key West with a party of 5...
3 hours and up Free Cancellation
4.9 (1,168)
from
$180
$180
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
4.9 (3,101)
Key West Original Island Jet Ski Tour
Get into some wet & wild watersports excitement on the best Key West jet ski tour around – a 90-minute adventure featuring 28 miles of...
1.5 Hours Free Cancellation
4.9 (3,101)
$120
Special Offer
4.9 (1,019)
Key West Parasailing Adventure
Float high above and parasail the Atlantic waters for a bird’s eye view of Florida’s beautiful Key West, the Southernmost Point in the US. This...
1 Hour Free Cancellation
4.9 (1,019)
$64
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
4.9 (2,739)
Key West Sail, Snorkel, Kayak with Sunset Option
Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....
4.5 or 6.5 hours (approx.) Free Cancellation
4.9 (2,739)
from
$105
$105
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
4.9 (2,739)
Key West Backcountry Safari
Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....
4.5 or 6.5 hours (approx.) Free Cancellation
4.9 (2,739)
from
$105
$105
The Key West Snorkel & Sunset Sail Rum & Reggae Combo checks your Key West bucket list items with snorkeling, a sunset cruise, and icy...
3 Hours Free Cancellation
4.8 (352)
from
$60
$60
4.7 (577)
Key West Morning Snorkel Trip
Our Key West Morning Snorkel Trip lets you start the day with sunshine, blue water, and adventure at sea as you experience the wonders of...
3 Hours Free Cancellation
4.7 (577)
from
$55
$55
4.8 (1,097)
Key West Dolphin Watch & Snorkel Combo
Explore the natural wonders of Key West with a visit to wild dolphins in their ocean home and a snorkel over the coral and sand...
3 Hours Free Cancellation
4.8 (1,097)
from
$80
$80
Make the most of your Key West water time — our Double Dip Key West Snorkeling Adventure lets you explore the underwater scenery at two...
3 Hours Free Cancellation
5.0 (955)
from
$80
$80
The Key West Glass Bottom Boat Tour combines an entertaining, educational exploration of the reefs & marine life around Key West with a classic sunset...
2 hours (approx.) Free Cancellation
4.6 (538)
from
$70
$70
Don’t miss this exciting Key West Afternoon Snorkel Trip that blends the best of Key West: sunshine, sail boats, blue water, colorful fish, and icy...
3 Hours Free Cancellation
4.7 (577)
from
$60
$60
Enjoy life like a Key West local with a picnic play day on the calm, clear waters and pure white sands of a Backcountry sandbar...
3.5 Hours (approx.) Free Cancellation
4.9 (621)
from
$120
$120
Special Offer
The beach pass is an all-day, all-inclusive package. Buy a combo package that includes parasailing or one that includes an umbrella, chairs, and all the...
All Day (9am - 5pm) Free Cancellation
4.7 (19)
$100
4.6 (1,765)
Key West Hop-On Hop-Off Old Town Tour Trolley
The hop-on hop-off trolley tour of Key West is a fantastic way to explore this historic island. Sit back and relax while your expert tour...
1 hour 30 minutes Free Cancellation
4.6 (1,765)
from
$56
$56
4.4 (1,409)
Key West Ghosts & Gravestones Tour
Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the...
1 hour Free Cancellation
4.4 (1,409)
from
$40
$40
4.5 (883)
Key West Conch Tour Train
Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attractions, the Conch Tour Train has been entertaining...
1 hour Free Cancellation
4.5 (883)
from
$45
$45
4.7 (501)
Key West Truman Little White House
Tour the historic Harry S. Truman Little White House in Key West and learn about a fascinating period of American history. What was once a...
1 to 2 hours Free Cancellation
4.7 (501)
from
$26
$26
4.0 (116)
Key West Shipwreck Treasure Museum
Learn about an important part of Florida’s history at the Key West Shipwreck Treasure Museum. Explore the wreckage of Spanish galleons and the remnants of...
2 hours Free Cancellation
4.0 (116)
from
$19
$19
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
5.0 (1,719)
Key West Wind & Wine Sunset Sail
Wind & Wine has been the #1 rated sunset sail on Cool Key West for over a decade. In our opinion, this is the best...
2 hours (approx.) Free Cancellation
5.0 (1,719)
$99
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
4.8 (505)
Key West Split Fishing Charter
Cool Key West presents the Key West Split Fishing Charter: the most cost-effective and convenient way to get offshore and enjoy some Key West sportfishing....
4 or 6 hours (approx.) Free Cancellation
4.8 (505)
$200
4.7 (148)
Key West Party Boat Fishing Charter
Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...
6 hours (approx.) Free Cancellation
4.7 (148)
from
$70
$70
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
The is the absolute best way for a person to experience diving. Great for those who want to try scuba diving in Key West....
9 hours (approx.) Free Cancellation
4.9 (146)
$229
Afternoon two-tank Key West Scuba dive trips offer divers the chance to explore two different dive sites on the pristine coral reef system of the...
4 hours 30 minutes (approx.) Free Cancellation
4.8 (132)
from
$99
$99
4.4 (1,934)
Key West Sunset Dinner Cruise
Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....
2 hours Free Cancellation
4.4 (1,934)
from
$93
$93
The morning two tank Key West Dive Trips are great because this includes a double dive in a Vandenberg wreck dive....
4 hours 30 minutes (approx.) Free Cancellation
4.9 (97)
from
$99
$99
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...
2 hours (approx.) Free Cancellation
4.8 (3,837)
from
$80
$80
Before Looking for a Great Adventure in Key West? Enter the amazing world of scuba diving the fun and easy way with PADI® Open Water...
2 days (approx.) Free Cancellation
5.0 (15)
from
$499
$499
Cool Key West brings you the ultimate Private Deep Sea Fishing Charter experience with a classic 63-foot sportfishing boat that can show 41 day-trip guests...
4-12 hours (approx.) Free Cancellation
4.9 (19)
from
$1,700
$1,700
This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great...
2 Hours (approx.) Free Cancellation
4.8 (996)
from
$80
$80
Special Offer
The Cool Key West Scuba Refresher course is a safe, fun skills review perfect for Open Water divers who have been out of the water...
8 hours (approx.) Free Cancellation
5.0 (22)
$225
Special Offer
4.9 (128)
Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...
2 hours (approx.) Hotel pickup offered Free Cancellation
4.9 (128)
$89
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Special Offer
4.9 (739)
Key West Ultimate Adventure
This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...
6 hours (approx.) Free Cancellation
4.9 (739)
$169
4.9 (268)
Key West Deep Sea Fishing Charter
Cool Key West takes you on a Key West Deep Sea Fishing Charter for high adventure and big fish on the deep blue waters that...
4, 6 or 8 hours (approx.) Free Cancellation
4.9 (268)
$900
4.8 (1,449)
Key West Snorkeling Adventure
Envision yourself swimming freely among the vibrant fish of the Florida Keys during a Key West snorkeling tour. This tranquil catamaran cruise provides easy snorkeling...
3 hours (approx.) Free Cancellation
4.8 (1,449)
from
$50
$50
Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...
2 hours (approx.) Free Cancellation
4.9 (1,704)
from
$100
$100
4.9 (61)
Key West Flats Fishing Charter
Take your own private boat and personal guide to hunt Bonefish, Permit, Sharks and other game fish in the crystal-clear waters of the Key West...
4, 6 or 8 hours (approx.) Free Cancellation
4.9 (61)
from
$580
$580
Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...
2 hours 30 minutes (approx.) Free Cancellation
4.8 (750)
from
$90
$90
4.6 (432)
Sunset Sip & Sail
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...
2 hours Free Cancellation
4.6 (432)
from
$77
$77
Cool Key West brings you a great value in thrilling Key West light tackle fishing with this Family-Friendly Fishing Tour on the calm inshore waters...
4 hours (approx.) Free Cancellation
4.9 (23)
$1,200
Enjoy the excitement of saltwater light tackle fishing as you hunt the reefs and wrecks for a world record catch with your own private boat...
4, 6 or 8 hours (approx.) Free Cancellation
4.9 (35)
from
$950
$950
4.7 (695)
Key West Snorkeling
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...
3 hours Free Cancellation
4.7 (695)
from
$54
$54
Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....
3 hours 30 minutes (approx.) Hotel pickup offered Free Cancellation
4.9 (25)
from
$99
$99
Key West Cruise Port Schedule
Key West cruise port schedule through January 2030.
| Day | Ship | Cruise | Arrival | Departure | Passengers |
|---|---|---|---|---|---|
| Saturday Nov 14, 2026 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Monday Nov 16, 2026 |
8 Night Key West, Celebration Key Bahamas, Princess Cays & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Tuesday Nov 17, 2026 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Nov 18, 2026 |
7 Night Key West, Bimini Islands & Nassau Cruise | 8:00 AM | 5:00 PM | 2,158 | |
| Friday Nov 20, 2026 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Nov 20–21, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Nov 21, 2026 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Nov 22, 2026 |
7 Night Key West, Ocho Rios, Grand Cayman Island & Cozumel Cruise | 8:00 AM | 2:00 PM | 1,970 | |
| Monday Nov 23–24, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Nov 24, 2026 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Nov 25, 2026 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Thursday Nov 26, 2026 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Friday Nov 27, 2026 |
7 Night Half Moon Cay, Puerto Plata-Amber Cove, Grand Turk Island & Key West Cruise | 8:00 AM | 5:00 PM | 2,104 | |
| Friday Nov 27–28, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Nov 28, 2026 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Nov 29, 2026 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Nov 30, 2026 |
8 Night Key West, Celebration Key Bahamas, Princess Cays & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Monday Nov 30 – Dec 1, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Dec 1, 2026 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Dec 1–2, 2026 |
15 Night St Augustine FL, Port Canaveral, West Palm Beach, Key Biscayne FL, Key West, Marco Island Florida & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Dec 1–2, 2026 |
15 Night Green Cove Springs FL, St Augustine FL, Port Canaveral, West Palm Beach, Key Biscayne FL, Key West, Marco Island Florida & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 2, 2026 |
7 Night Key West, Bimini Islands & Nassau Cruise | 8:00 AM | 5:00 PM | 2,158 | |
| Thursday Dec 3, 2026 |
5 Night Freeport, Great Stirrup Cay & Key West Cruise | 9:00 AM | 5:00 PM | 2,340 | |
| Friday Dec 4, 2026 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Dec 4–5, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Dec 5, 2026 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Dec 6, 2026 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Dec 7, 2026 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Dec 7–8, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Dec 8, 2026 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 9–10, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 10, 2026 |
12 Night Philipsburg St Maarten, Fort-de-France, Bridgetown, Scarborough, Castries, Basseterre St Kitts & Key West Cruise | 8:00 AM | 5:00 PM | 2,106 | |
| Friday Dec 11, 2026 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Dec 11–12, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Dec 12, 2026 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Dec 13, 2026 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Dec 14, 2026 |
8 Night Key West, Celebration Key Bahamas, Princess Cays & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Monday Dec 14–15, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Dec 15, 2026 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 16, 2026 |
5 Night Key West & Great Stirrup Cay Cruise | 7:00 AM | 3:00 PM | 2,340 | |
| Wednesday Dec 16–17, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 17, 2026 |
7 Night Bimini Islands, Key West & Freeport Cruise | 7:00 AM | 5:00 PM | 2,158 | |
| Friday Dec 18, 2026 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Dec 18–19, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Dec 19, 2026 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Dec 20, 2026 |
14 Night Key West, Willemstad Curacao, Oranjestad Aruba, Santa Marta Colombia, Cartagena Colombia, Panama Canal, Manta & Guayaquil Cruise | 7:00 AM | 1:00 PM | 698 | |
| Monday Dec 21–22, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Dec 22, 2026 |
7 Night Key West, Cozumel & Grand Cayman Island Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 23, 2026 |
14 Night Key West, Oranjestad Aruba, Charlotteville, St Georges Grenada, Bridgetown, Castries, San Juan & Half Moon Cay Cruise | 8:00 AM | 4:00 PM | 1,432 | |
| Wednesday Dec 23–24, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 24, 2026 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Friday Dec 25, 2026 |
7 Night Puerto Plata-Amber Cove, Grand Turk Island, Half Moon Cay & Key West Cruise | 8:00 AM | 6:00 PM | 1,970 | |
| Friday Dec 25–26, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Dec 26, 2026 |
7 Night Half Moon Cay, Grand Turk Island, Puerto Plata-Amber Cove & Key West Cruise | 8:00 AM | 5:00 PM | 2,106 | |
| Sunday Dec 27, 2026 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Dec 28, 2026 |
8 Night Key West, Celebration Key Bahamas, Princess Cays & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Monday Dec 28–29, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Dec 29, 2026 |
7 Night Key West, Bimini Islands & Nassau Cruise | 7:00 AM | 5:00 PM | 2,158 | |
| Wednesday Dec 30–31, 2026 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Jan 1–2, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Sunday Jan 3, 2027 |
7 Night Key West, Puerto Plata-Amber Cove, Grand Turk Island & Half Moon Cay Cruise | 8:00 AM | 4:00 PM | 2,104 | |
| Monday Jan 4, 2027 |
5 Night Key West & Cozumel Cruise | 8:00 AM | 5:00 PM | 2,850 | |
| Monday Jan 4–5, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Jan 5, 2027 |
8 Night Key West, Celebration Key Bahamas, Half Moon Cay & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Wednesday Jan 6, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jan 6–7, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Jan 8, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jan 8–9, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Jan 9, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 10, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Jan 11, 2027 |
10 Night Half Moon Cay, Falmouth Jamaica, Grand Cayman Island, Belize City, Cozumel & Key West Cruise | 8:00 AM | 5:00 PM | 2,680 | |
| Monday Jan 11–12, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Jan 12, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jan 13, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Wednesday Jan 13–14, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Jan 15, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jan 15–16, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Jan 16, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 17, 2027 |
3 Night Freeport & Key West Cruise | 8:00 AM | 5:00 PM | 2,150 | |
| Monday Jan 18, 2027 |
14 Night Key West, Grand Turk Island, San Juan, St Thomas Island USVI, Basseterre St Kitts, Philipsburg St Maarten, St Croix Island USVI & Ocho Rios Cruise | 12:00 PM | 6:00 PM | 3,646 | |
| Monday Jan 18–19, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Jan 19, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Jan 20, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jan 20–21, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Jan 21, 2027 |
5 Night Key West & Great Stirrup Cay Cruise | 7:00 AM | 3:00 PM | 2,340 | |
| Friday Jan 22, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jan 22–23, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Jan 23, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 24, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Jan 25, 2027 |
6 Night Key West, Grand Turk Island & Puerto Plata-Amber Cove Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Monday Jan 25–26, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Jan 27, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,150 | |
| Wednesday Jan 27–28, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Jan 28, 2027 |
9 Night Ocho Rios, Santo Tomas de Castilla, Roatan Island, Belize City & Key West Cruise | 10:00 AM | 9:00 PM | 922 | |
| Friday Jan 29, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jan 29–30, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Sunday Jan 31, 2027 |
6 Night Key West, Montego Bay & Grand Cayman Island Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Monday Feb 1, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Feb 1–2, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Feb 2, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Feb 3, 2027 |
5 Night Key West & Cozumel Cruise | 8:00 AM | 4:30 PM | 2,376 | |
| Wednesday Feb 3–4, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Feb 4, 2027 |
7 Night Tortola Island BVI, St John's Antigua, Providenciales Island & Key West Cruise | 8:30 AM | 5:30 PM | 926 | |
| Friday Feb 5–6, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Sunday Feb 7, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Feb 8, 2027 |
8 Night Key West, Celebration Key Bahamas, Princess Cays & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Monday Feb 8–9, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Feb 10–11, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Feb 11, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 4:00 PM | 2,708 | |
| Friday Feb 12, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Feb 12–13, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Feb 13, 2027 |
9 Night Key West, Great Stirrup Cay, Cabo Rojo-Pedernales, Falmouth Jamaica & Grand Cayman Island Cruise | 11:00 AM | 5:00 PM | 2,394 | |
| Sunday Feb 14, 2027 |
10 Night Key West, Grand Cayman Island, Ocho Rios, Roatan Island, Belize City & Cozumel Cruise | 7:30 AM | 5:00 PM | 2,680 | |
| Monday Feb 15, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Feb 15–16, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Feb 16, 2027 |
5 Night Key West & Freeport Cruise | 12:00 PM | 6:00 PM | 2,210 | |
| Wednesday Feb 17–18, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Feb 19, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Feb 19–20, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Sunday Feb 21, 2027 |
7 Night Key West, Bimini Islands, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Feb 22, 2027 |
8 Night Key West, Celebration Key Bahamas, Princess Cays & Nassau Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Monday Feb 22–23, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Feb 24, 2027 |
4 Night Coco Cay & Key West Cruise | 9:00 AM | 6:00 PM | 2,150 | |
| Thursday Feb 25, 2027 |
7 Night Cozumel, Progreso & Key West Cruise | 8:00 AM | 6:00 PM | 2,210 | |
| Friday Feb 26, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Feb 26–27, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Sunday Feb 28, 2027 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Mar 1, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Mar 1–2, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Mar 3, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Thursday Mar 4, 2027 |
5 Night Key West & Great Stirrup Cay Cruise | 7:00 AM | 3:00 PM | 2,340 | |
| Friday Mar 5, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Mar 5–6, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Mar 6, 2027 |
5 Night Key West & Ocho Rios Cruise | 7:00 AM | 1:30 PM | 2,376 | |
| Sunday Mar 7, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Mar 8, 2027 |
8 Night Key West, Celebration Key Bahamas, Nassau & Half Moon Cay Cruise | 8:00 AM | 4:00 PM | 2,124 | |
| Monday Mar 8–9, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Mar 10, 2027 |
7 Night Bimini Islands, Key West & Cozumel Cruise | 7:00 AM | 6:00 PM | 2,158 | |
| Friday Mar 12, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Mar 12–13, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Monday Mar 15, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Mar 15–16, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Mar 16, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Mar 17, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Friday Mar 19, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Mar 19–20, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Mar 20, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Mar 21, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Mar 22–23, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Mar 23, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Mar 24, 2027 |
4 Night Coco Cay & Key West Cruise | 9:00 AM | 6:00 PM | 2,150 | |
| Thursday Mar 25, 2027 |
4 Night Key West & Half Moon Cay Cruise | 7:00 AM | 6:00 PM | 1,970 | |
| Friday Mar 26, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Mar 26–27, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Mar 27, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Mar 28, 2027 |
7 Night Key West, Grand Cayman Island, Montego Bay & Nassau Cruise | 8:00 AM | 4:00 PM | 2,708 | |
| Monday Mar 29, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Mar 29–30, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Mar 30, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Mar 31, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Thursday Apr 1, 2027 |
5 Night Key West & Great Stirrup Cay Cruise | 7:00 AM | 3:00 PM | 2,340 | |
| Friday Apr 2–3, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Apr 3, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Apr 4, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Apr 5, 2027 |
7 Night Key West, Ocho Rios, Grand Cayman Island & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Monday Apr 5–6, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Apr 6, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Apr 7, 2027 |
5 Night Key West & Freeport Cruise | 7:00 AM | 3:00 PM | 2,210 | |
| Friday Apr 9, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Apr 9–10, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Apr 10, 2027 |
7 Night Grand Turk Island, Puerto Plata-Amber Cove, Bimini Islands & Key West Cruise | 9:00 AM | 5:00 PM | 448 | |
| Sunday Apr 11, 2027 |
7 Night Gustavia St Barths, Montserrat Island UK, Basseterre St Kitts & Key West Cruise | 9:00 AM | 6:30 PM | 926 | |
| Monday Apr 12, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Apr 12–13, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Apr 13, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Apr 14, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 4:00 PM | 1,316 | |
| Thursday Apr 15, 2027 |
7 Night Grand Turk Island, Nassau & Key West Cruise | 7:00 AM | 5:00 PM | 3,046 | |
| Friday Apr 16–17, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Apr 17, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Apr 18, 2027 |
7 Night Key West, Ocho Rios, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Apr 19–20, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday Apr 20, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Apr 21, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Apr 23, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Apr 24, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Apr 25–26, 2027 |
15 Night St Petersburg FL, Punta Gorda Florida, Marco Island Florida, Key West, Key Biscayne FL, West Palm Beach, Port Canaveral, Green Cove Springs FL & St Augustine FL Cruise | Overnight | 112 | ||
| Monday Apr 26, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Monday Apr 26–27, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Apr 29, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday May 1, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Monday May 3–4, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Tuesday May 4, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Friday May 7, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday May 8, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday May 9, 2027 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday May 10, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,646 | |
| Tuesday May 11, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday May 12, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Wednesday May 12–13, 2027 |
15 Night St Petersburg FL, Punta Gorda Florida, Marco Island Florida, Key West, Key Biscayne FL, West Palm Beach, Port Canaveral, Green Cove Springs FL & St Augustine FL Cruise | Overnight | 112 | ||
| Saturday May 15, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday May 16, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Tuesday May 18, 2027 |
4 Night Key West & Coco Cay Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday May 19, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday May 21, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday May 22, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday May 23, 2027 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday May 24, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,690 | |
| Tuesday May 25, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday May 26, 2027 |
4 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Saturday May 29, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday May 30, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Tuesday Jun 1, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jun 2, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Jun 4, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jun 5, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jun 6, 2027 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Jun 8, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Saturday Jun 12, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jun 13, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Tuesday Jun 15, 2027 |
4 Night Key West & Coco Cay Cruise | 7:00 AM | 3:30 PM | 3,046 | |
| Wednesday Jun 16, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Jun 18, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jun 19, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jun 20, 2027 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Jun 21, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,690 | |
| Tuesday Jun 22, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Jun 23, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Saturday Jun 26, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Monday Jun 28, 2027 |
7 Night Key West, Grand Cayman Island & Ocho Rios Cruise | 7:00 AM | 5:00 PM | 2,708 | |
| Wednesday Jun 30, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 4:00 PM | 1,316 | |
| Thursday Jul 1, 2027 |
4 Night Coco Cay & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Friday Jul 2, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jul 3, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jul 4, 2027 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Jul 6, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Saturday Jul 10, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jul 11, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Tuesday Jul 13, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jul 14, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Jul 16, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jul 17, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jul 18, 2027 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Jul 19, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,690 | |
| Tuesday Jul 20, 2027 |
4 Night Key West & Nassau Cruise | 7:00 AM | 3:00 PM | 3,046 | |
| Sunday Jul 25, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Wednesday Jul 28, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Jul 30, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jul 31, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Aug 3, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Aug 4, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Saturday Aug 7, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Aug 8, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Thursday Aug 12, 2027 |
4 Night Coco Cay & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Friday Aug 13, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Aug 14, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Monday Aug 16, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,690 | |
| Tuesday Aug 17, 2027 |
4 Night Key West & Coco Cay Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Aug 18, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Tuesday Aug 24, 2027 |
4 Night Key West & Coco Cay Cruise | 7:00 AM | 3:00 PM | 2,144 | |
| Friday Aug 27, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Monday Aug 30, 2027 |
6 Night Key West, Grand Cayman Island & Cozumel Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Aug 31, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Friday Sep 3, 2027 |
4 Night Key West & Freeport Cruise | 10:00 AM | 6:00 PM | 1,316 | |
| Sunday Sep 5, 2027 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Sep 6, 2027 |
5 Night Key West, Bimini Islands & Freeport Cruise | 8:00 AM | 4:00 PM | 2,708 | |
| Thursday Sep 9, 2027 |
4 Night Coco Cay & Key West Cruise | 8:00 AM | 5:00 PM | 2,144 | |
| Friday Sep 10, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Monday Sep 13, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,690 | |
| Tuesday Sep 14, 2027 |
5 Night Key West & Grand Cayman Island Cruise | 8:00 AM | 4:00 PM | 2,708 | |
| Wednesday Sep 15, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Sep 17, 2027 |
6 Night Grand Turk Island, Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Sep 19, 2027 |
7 Night Key West, Grand Cayman Island, Ocho Rios & Nassau Cruise | 7:00 AM | 3:00 PM | 2,708 | |
| Thursday Sep 23, 2027 |
4 Night Coco Cay & Key West Cruise | 9:00 AM | 6:00 PM | 2,144 | |
| Friday Sep 24, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Monday Sep 27, 2027 |
6 Night Key West, Grand Cayman Island & Cozumel Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Oct 3, 2027 |
7 Night Key West, Roatan Island, Belize City & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Oct 5, 2027 |
4 Night Key West & Coco Cay Cruise | 7:00 AM | 3:00 PM | 2,144 | |
| Wednesday Oct 6, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Friday Oct 8, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Monday Oct 11, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 10:00 AM | 6:00 PM | 3,690 | |
| Tuesday Oct 12, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Oct 13, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Saturday Oct 16, 2027 |
3 Night Key West & Coco Cay Cruise | 7:00 AM | 3:00 PM | 2,144 | |
| Monday Oct 18, 2027 |
14 Night Key West, Celebration Key Bahamas, San Juan, St Thomas Island USVI, Basseterre St Kitts, Philipsburg St Maarten, St Croix Island USVI & Ocho Rios Cruise | 11:30 AM | 5:00 PM | 3,690 | |
| Thursday Oct 21, 2027 |
4 Night Coco Cay & Key West Cruise | 9:00 AM | 6:00 PM | 2,144 | |
| Friday Oct 22, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Sunday Oct 24, 2027 |
7 Night Key West, Grand Cayman Island & Montego Bay Cruise | 11:00 AM | 7:00 PM | 2,210 | |
| Monday Oct 25, 2027 |
6 Night Key West, Grand Cayman Island & Cozumel Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Oct 27, 2027 |
4 Night Key West & Coco Cay Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Friday Oct 29, 2027 |
7 Night Half Moon Cay, Grand Turk Island, Puerto Plata-Amber Cove & Key West Cruise | 8:00 AM | 5:00 PM | 2,104 | |
| Sunday Oct 31, 2027 |
5 Night Key West & Cozumel Cruise | 10:00 AM | 6:00 PM | 1,316 | |
| Wednesday Nov 3, 2027 |
6 Night Nassau, Coco Cay & Key West Cruise | 9:30 AM | 5:00 PM | 2,284 | |
| Friday Nov 5, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Nov 6, 2027 |
4 Night Key West & Freeport Cruise | 7:00 AM | 4:00 PM | 1,316 | |
| Sunday Nov 7, 2027 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Nov 8, 2027 |
6 Night Key West, Cozumel & Grand Cayman Island Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Tuesday Nov 9, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Thursday Nov 11, 2027 |
4 Night Coco Cay & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Thursday Nov 11–12, 2027 |
15 Night St Augustine FL, Port Canaveral, West Palm Beach, Key Biscayne FL, Key West, Marco Island Florida & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Saturday Nov 13, 2027 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Monday Nov 15, 2027 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,984 | |
| Tuesday Nov 16, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Nov 16–17, 2027 |
15 Night Green Cove Springs FL, St Augustine FL, Port Canaveral, West Palm Beach, Key Biscayne FL, Key West, Marco Island Florida & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Nov 17, 2027 |
7 Night Bimini Islands, Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Thursday Nov 18, 2027 |
7 Night St Thomas Island USVI, Catalina Island, Puerto Plata-Amber Cove, Key West & MSC Ocean Cay Cruise | 9:00 AM | 5:00 PM | 926 | |
| Saturday Nov 20, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Nov 21, 2027 |
7 Night Key West, Grand Cayman Island & Freeport Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Tuesday Nov 23, 2027 |
4 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Nov 24, 2027 |
7 Night Freeport, Key West & Grand Cayman Island Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Wednesday Nov 24–25, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Nov 25, 2027 |
5 Night Key West & Freeport Cruise | 7:00 AM | 3:00 PM | 2,210 | |
| Friday Nov 26, 2027 |
6 Night Nassau, Grand Cayman Island & Key West Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Saturday Nov 27, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Nov 28, 2027 |
5 Night Nassau, Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 448 | |
| Tuesday Nov 30, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 1–2, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 2, 2027 |
7 Night Exuma Islands, Grand Turk Island, Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 388 | |
| Friday Dec 3, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Dec 4, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Dec 5, 2027 |
7 Night Key West, Cozumel & Grand Cayman Island Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Dec 6, 2027 |
6 Night Key West, Grand Cayman Island & Nassau Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Tuesday Dec 7, 2027 |
7 Night Key West, Belize City & Costa Maya Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Wednesday Dec 8, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 8–9, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 9, 2027 |
7 Night Exuma Islands, Grand Turk Island, Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 388 | |
| Saturday Dec 11, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Dec 12, 2027 |
7 Night Key West, Roatan Island, Cozumel & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Dec 14, 2027 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 15, 2027 |
7 Night Grand Turk Island, Exuma Islands, Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 388 | |
| Wednesday Dec 15–16, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 16, 2027 |
4 Night Nassau & Key West Cruise | 7:00 AM | 5:00 PM | 2,144 | |
| Friday Dec 17, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Dec 18, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Dec 19, 2027 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Wednesday Dec 22, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 22–23, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 23, 2027 |
14 Night Key West, Cozumel, Santo Tomas de Castilla, Harvest Caye Belize, Roatan Island, Puerto Limon, Panama Canal, Colon, Falmouth Jamaica & Grand Cayman Island Cruise | 8:00 AM | 4:00 PM | 750 | |
| Friday Dec 24, 2027 |
5 Night Key West & Grand Cayman Island Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Saturday Dec 25, 2027 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Dec 28, 2027 |
3 Night Key West & Nassau Cruise | 7:00 AM | 3:00 PM | 2,144 | |
| Wednesday Dec 29, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Dec 29–30, 2027 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Dec 30, 2027 |
11 Night Key West, St Thomas Island USVI, Tortola Island BVI, Gustavia St Barths, St John's Antigua & St John Island USVI Cruise | 8:00 AM | 3:00 PM | 726 | |
| Friday Dec 31, 2027 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jan 1, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Monday Jan 3, 2028 |
7 Night Key West, Belize City & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Jan 4, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Jan 5, 2028 |
4 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jan 5–6, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Jan 6, 2028 |
7 Night Bimini Islands, Freeport & Key West Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Saturday Jan 8, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 9, 2028 |
5 Night Nassau, Freeport & Key West Cruise | 8:00 AM | 5:00 PM | 2,158 | |
| Monday Jan 10, 2028 |
7 Night Key West, Ocho Rios, Grand Cayman Island & Bimini Islands Cruise | 8:00 AM | 4:00 PM | 2,816 | |
| Tuesday Jan 11, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jan 12–13, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Jan 13, 2028 |
9 Night Cozumel, Costa Maya, Santo Tomas de Castilla, Belize City, Key West & MSC Ocean Cay Cruise | 9:00 AM | 5:00 PM | 926 | |
| Saturday Jan 15, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 16, 2028 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Jan 17, 2028 |
6 Night Key West, Grand Cayman Island & Nassau Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Tuesday Jan 18, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Jan 19, 2028 |
4 Night Freeport & Key West Cruise | 7:00 AM | 5:00 PM | 2,144 | |
| Wednesday Jan 19–20, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Jan 20, 2028 |
4 Night Freeport & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Friday Jan 21, 2028 |
7 Night Nassau, Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Saturday Jan 22, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 23, 2028 |
7 Night Key West, Belize City & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Jan 24, 2028 |
6 Night Key West, Grand Cayman Island & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Tuesday Jan 25, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Jan 26, 2028 |
7 Night Bimini Islands, Key West & Grand Cayman Island Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Wednesday Jan 26–27, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Jan 28, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Jan 29, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Jan 30, 2028 |
7 Night Key West, Falmouth Jamaica & Grand Cayman Island Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Tuesday Feb 1, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Feb 2, 2028 |
4 Night Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Feb 2–3, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Feb 3, 2028 |
7 Night Grand Cayman Island, Key West & Freeport Cruise | 7:00 AM | 5:00 PM | 2,130 | |
| Saturday Feb 5, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Feb 6, 2028 |
11 Night Key West, Cozumel, Santo Tomas de Castilla, Harvest Caye Belize, Roatan Island, Falmouth Jamaica & Grand Cayman Island Cruise | 7:00 AM | 5:00 PM | 822 | |
| Monday Feb 7, 2028 |
7 Night Key West, Belize City & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Feb 8, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Feb 9, 2028 |
7 Night Bimini Islands, Key West & Grand Cayman Island Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Wednesday Feb 9–10, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Feb 10, 2028 |
14 Night Key West, Costa Maya, Cozumel, Progreso, Galveston, New Orleans & Tampa Cruise | 8:00 AM | 6:00 PM | 502 | |
| Friday Feb 11, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Feb 12, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Feb 15, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Feb 16, 2028 |
4 Night Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Feb 16–17, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Feb 17, 2028 |
7 Night Grand Cayman Island, Cozumel & Key West Cruise | 8:00 AM | 5:00 PM | 2,934 | |
| Friday Feb 18, 2028 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Saturday Feb 19, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Feb 22, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Feb 22, 2028 |
4 Night Key West & Great Stirrup Cay Cruise | 8:00 AM | 5:00 PM | 3,292 | |
| Wednesday Feb 23, 2028 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Wednesday Feb 23–24, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Feb 24, 2028 |
13 Night Key West, Jost Van Dyke Island BVI, Gustavia St Barths, St John's Antigua, Fort-de-France, Castries, Bridgetown, Mayreau Island & Kralendijk Bonaire Cruise | 9:00 AM | 5:00 PM | 502 | |
| Saturday Feb 26, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Feb 29, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Mar 1, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 2,158 | |
| Wednesday Mar 1–2, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Mar 2, 2028 |
4 Night Freeport & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Friday Mar 3, 2028 |
12 Night Key West, Grand Cayman Island, Falmouth Jamaica, Cabo Rojo-Pedernales, Cartagena Colombia, Puerto Limon & Panama Canal Cruise | 8:00 AM | 4:00 PM | 822 | |
| Saturday Mar 4, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Mar 5, 2028 |
25 Night New Orleans, Tampa, Key West, Miami, Hamilton, Horta, Ponta Delgada & Vigo Cruise | 8:00 AM | 7:00 PM | 838 | |
| Tuesday Mar 7, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Mar 7, 2028 |
4 Night Key West & Great Stirrup Cay Cruise | 8:00 AM | 5:00 PM | 3,292 | |
| Wednesday Mar 8, 2028 |
5 Night Costa Maya & Key West Cruise | 8:00 AM | 5:00 PM | 2,158 | |
| Wednesday Mar 8–9, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Mar 9, 2028 |
7 Night St Thomas Island USVI, Samana, Puerto Plata-Amber Cove, Key West & MSC Ocean Cay Cruise | 9:00 AM | 6:00 PM | 926 | |
| Friday Mar 10, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Mar 11, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Mar 12, 2028 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Monday Mar 13, 2028 |
6 Night Key West, Grand Cayman Island & Nassau Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Tuesday Mar 14, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Mar 15, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Mar 15–16, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Mar 16, 2028 |
7 Night Grand Cayman Island, Cozumel & Key West Cruise | 8:00 AM | 5:00 PM | 2,934 | |
| Friday Mar 17, 2028 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Saturday Mar 18, 2028 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Mar 19, 2028 |
4 Night Bimini Islands & Key West Cruise | 8:00 AM | 5:00 PM | 448 | |
| Tuesday Mar 21, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Mar 22, 2028 |
7 Night Bimini Islands, Key West & Grand Cayman Island Cruise | 8:00 AM | 5:00 PM | 2,130 | |
| Wednesday Mar 22–23, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Mar 23, 2028 |
11 Night Key West, Tampa, Mobile, New Orleans & Cozumel Cruise | 8:00 AM | 5:00 PM | 722 | |
| Friday Mar 24, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Mar 25, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Mar 26, 2028 |
7 Night Key West, Grand Cayman Island & Ocho Rios Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Mar 28, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Mar 29, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Mar 29–30, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Mar 30, 2028 |
7 Night Grand Cayman Island, Cozumel & Key West Cruise | 8:00 AM | 5:00 PM | 2,934 | |
| Saturday Apr 1, 2028 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Apr 2, 2028 |
5 Night Key West & Progreso Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Apr 4, 2028 |
4 Night Key West & Nassau Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Apr 5, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,158 | |
| Wednesday Apr 5–6, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Apr 6, 2028 |
7 Night St Thomas Island USVI, Samana, Puerto Plata-Amber Cove, Key West & MSC Ocean Cay Cruise | 9:00 AM | 6:00 PM | 926 | |
| Saturday Apr 8, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Apr 9, 2028 |
7 Night Key West, Grand Cayman Island & Cozumel Cruise | 10:30 AM | 5:00 PM | 2,934 | |
| Monday Apr 10, 2028 |
6 Night Key West, Grand Cayman Island & Nassau Cruise | 8:00 AM | 5:00 PM | 2,898 | |
| Tuesday Apr 11, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Apr 12–13, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Apr 13, 2028 |
4 Night Nassau & Key West Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Saturday Apr 15, 2028 |
3 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Sunday Apr 16, 2028 |
5 Night Key West & Cozumel Cruise | 1:00 PM | 7:00 PM | 2,210 | |
| Tuesday Apr 18, 2028 |
4 Night Key West & Coco Cay Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Wednesday Apr 19–20, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Apr 20, 2028 |
4 Night Nassau & Key West Cruise | 7:00 AM | 5:00 PM | 2,144 | |
| Friday Apr 21, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Saturday Apr 22, 2028 |
3 Night Key West & Freeport Cruise | 8:00 AM | 5:00 PM | 3,046 | |
| Tuesday Apr 25, 2028 |
7 Night Key West, Celebration Key Bahamas & Nassau Cruise | 8:00 AM | 4:00 PM | 2,978 | |
| Wednesday Apr 26–27, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday May 5, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday May 5–6, 2028 |
15 Night St Petersburg FL, Punta Gorda Florida, Marco Island Florida, Key West, Key Biscayne FL, West Palm Beach, Port Canaveral, Green Cove Springs FL & St Augustine FL Cruise | Overnight | 112 | ||
| Friday May 19, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jun 2, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jun 16, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jun 30, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jul 14, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Jul 28, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Aug 11, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Aug 25, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Sep 8, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Sep 22, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Oct 6, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Friday Oct 20, 2028 |
4 Night Key West & Bimini Islands Cruise | 8:00 AM | 5:00 PM | 2,816 | |
| Sunday Nov 19, 2028 |
7 Night Key West, Harvest Caye Belize, Roatan Island & Cozumel Cruise | 7:00 AM | 5:00 PM | 822 | |
| Sunday Nov 26, 2028 |
10 Night Key West, Grand Cayman Island, Santo Tomas de Castilla, Harvest Caye Belize & Cozumel Cruise | 8:00 AM | 4:00 PM | 1,226 | |
| Wednesday Nov 29–30, 2028 |
15 Night Green Cove Springs FL, St Augustine FL, Port Canaveral, West Palm Beach, Key Biscayne FL, Key West, Marco Island Florida & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 6–7, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 13–14, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 20–21, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 27–28, 2028 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Dec 29, 2028 |
10 Night Key West, Grand Cayman Island, Santo Tomas de Castilla, Harvest Caye Belize & Cozumel Cruise | 8:00 AM | 4:00 PM | 1,226 | |
| Wednesday Jan 3–4, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Jan 10–11, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Jan 17–18, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Jan 24–25, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Jan 31 – Feb 1, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Friday Apr 13–14, 2029 |
15 Night St Petersburg FL, Punta Gorda Florida, Marco Island Florida, Key West, Key Biscayne FL, West Palm Beach, Port Canaveral, Green Cove Springs FL & St Augustine FL Cruise | Overnight | 112 | ||
| Wednesday Nov 14–15, 2029 |
15 Night Green Cove Springs FL, St Augustine FL, Port Canaveral, West Palm Beach, Key Biscayne FL, Key West, Marco Island Florida & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Nov 21–22, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Nov 28–29, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 5–6, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 12–13, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 19–20, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Wednesday Dec 26–27, 2029 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 | ||
| Thursday Jan 3–4, 2030 |
8 Night Marco Island Florida, Key West & Punta Gorda Florida Cruise | Overnight | 112 |
Key West Shore Excursions Overview
Cool Key West offers a wide variety of shore excursions for those looking to explore the Florida Keys. From family-friendly activities like kayaking and snorkeling to more adventurous options like fishing, diving, and jet skiing, they have something for everyone. No matter what your level of experience is, their experienced guides will make sure everyone has a great time.
For those who want to explore the area’s diverse marine life, their snorkeling and diving excursions offer a great way to do just that. Whether you’re looking to spot sea turtles, dolphins, or other unique species, their knowledgeable guides can help you find the perfect spot. They also offer kayaking trips, which allow you to explore the area’s mangroves, creeks, and lagoons.
For those who want to explore Key West’s rich history, their historical tours are a great way to do so. During these tours, you can learn about the area’s past, and hear stories about pirates, shipwrecks, and other local legends.
For those looking to get out on the open water, Cool Key West offers a variety of fishing trips, including bottom fishing, trolling, drift fishing, and more. Whether you’re an experienced angler or a total beginner, their knowledgeable guides will make sure you have a great time.
Finally, for those looking for a more adventurous experience, their jet skiing, parasailing, and tubing trips are a great way to get your adrenaline pumping. These trips offer a unique way to explore not only the area’s waters but also its beautiful scenery.
No matter what type of shore excursion you’re looking for, Cool Key West has something for everyone. So, if you’re looking for a unique way to explore the area, be sure to check out their shore excursions.
Frequently Asked Questions
What is the best way to get around Key West?
What are the best options for Key West Shore Excursions?
What are the best kid-friendly options for Key West Shore Excursions Activities?
Which Key West Shore Excursions have Instant Confirmation?
Which Key West Shore Excursions have Free Cancellation?
Why book shore excursions with Cool Key West instead of my cruise line?
How do I find shore excursions that fit my cruise?
Can I book for a group, children or someone with limited mobility?
Do I earn rewards on shore excursions?
What does Guaranteed Return to Ship mean?
How much time should I leave before all-aboard?
What if my ship arrives late or its hours in port change?
What if my ship skips Key West?
What's the best way to see Key West in a day in port?
Where do cruise ships dock in Key West?
Where do I meet my tour?
What should I bring ashore?
Who do I contact if something goes wrong on the day?
Can I cancel my shore excursion?
What if my tour is canceled because of the weather?
Can I change my shore excursion after booking?
Is Cool Key West legit?
Select cruise
Discover Key West
Key West Wind & Wine Sunset Sail
Prices from $99
Key West Original Island Jet Ski Tour
Prices from $120
Key West Ultimate Adventure
Prices from $169
Key West 4 Seater EZGO Golf Cart Rental
Prices from $99
Key West Dolphin Watch & Snorkel Tour with FREE shuttle to location
Prices from $99
Key West Split Fishing Charter
Prices from $200
Key West Backcountry Safari
Prices from $105
Key West Dive in a Day Scuba Resort Course
Prices from $229
Key West Sail, Snorkel, Kayak with Sunset Option
Prices from $105
Key West 6 Seater Electric Car Rental
Prices from $180
Celebrity Reflection
Sat, Nov 14 • 8:00 AM
Carnival Spirit
Mon, Nov 16 • 8:00 AMCelebrity Reflection
Tue, Nov 17 • 8:00 AM
Celebrity Summit
Wed, Nov 18 • 8:00 AM
Scarlet Lady
Fri, Nov 20 • 8:00 AM
ACL American Maverick
Fri, Nov 20 • OvernightCelebrity Reflection
Sat, Nov 21 • 8:00 AM
ms Zuiderdam
Sun, Nov 22 • 8:00 AM
ACL American Pioneer
Mon, Nov 23 • OvernightCelebrity Reflection
Tue, Nov 24 • 8:00 AM
Margaritaville At Sea Paradise
Wed, Nov 25 • 7:00 AM
Margaritaville At Sea Islander
Thu, Nov 26 • 1:00 PMCelebrity Reflection
Celebrity CruisesCarnival Spirit
Carnival Cruise LineCelebrity Summit
Celebrity CruisesScarlet Lady
Virgin VoyagesACL American Maverick
American Cruise Linesms Zuiderdam
Holland AmericaACL American Pioneer
American Cruise LinesMargaritaville At Sea Paradise
Margaritaville at SeaMargaritaville At Sea Islander
Margaritaville at Sea
ms Eurodam
Holland America
Celebrity Apex
Celebrity Cruises
ACL American Patriot
American Cruise LinesCelebrity Cruises
6 shipsCarnival Cruise Line
5 shipsVirgin Voyages
4 shipsAmerican Cruise Lines
4 shipsHolland America
5 shipsMargaritaville at Sea
3 ships
Norwegian Cruise Line
4 ships
Oceania Cruises
2 ships
Royal Caribbean
3 ships
MSC Explora Journeys
3 ships
Ritz-Carlton Yacht Collection
1 ship
