New Year’s Eve in Key West

What better way to bring in the New Year than with an awesome water adventure with Cool Key West? Choose from one of our all-inclusive water sports packages, backcountry eco tours, or set sail into the night on a sunset cruise with complimentary drinks and snacks. At Cool Key West, we’ve gone the extra mile to help you bring in the new year in style. May you have a wonderful new year in Key West!

Key West Sunset Cruise
3
Key West Sunset Cruise with Live Music, Unlimited Beer & Wine. Join Sunset Watersports out on the water on our custom 65 foot catamaran for...
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2 hours Instant Confirmation
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Schooner Appledore Key West Day and Sunset Cruises with Full Bar
26
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...
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2 hours Instant Confirmation
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Sunset Sip & Sail
7
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...
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2 hours Instant Confirmation
from
$56.19
Details
from
$56.19
Details
Key West Sunset Snorkel Sail
5
Enjoy this 3 hour sunset combo trip. We will sail out to Key West’s best reef location, where you are welcome to jump in and...
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3 hours Instant Confirmation
from
$56.19
Details
from
$56.19
Details
Key West Dolphin Watch Sunset Snorkel Cruise
3
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous...
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3 hours Instant Confirmation
from
$74.95
Details
from
$74.95
Details
Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar
255
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern...
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2 hours Instant Confirmation
from
$69.95
Details
from
$69.95
Details
Key West Sunset Party Cruise
80
Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll...
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2 hours Instant Confirmation
from
$63
Details
from
$63
Details
Key West Sunset Champagne Cruise
79
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy...
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1 hour 30 minutes Instant Confirmation
from
$45.95
Details
from
$45.95
Details
Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar
30
Picture the perfect Key West sunset, as you sail and sit on the deck of a romantic two-masted schooner. With the wind blowing in your...
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2 hours Instant Confirmation
from
$79.95
Details
from
$79.95
Details
Snorkel and Sunset Sail: Rum n’ Reggae
25
This Caribbean-themed trip offers two bucket list items that Key West is famous for - a tropical coral reef and amazing sunsets. Rum punch, lively reggae...
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3 hours Instant Confirmation
from
$49.34
Details
from
$49.34
Details
Key West Glass-Bottom Boat Tour with Sunset Option
85
See the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat tour from Key West! As you relax on...
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2 hours Instant Confirmation
from
$49.77
Details
from
$49.77
Details
Key West Sunset Dinner Cruise
92
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....
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2 hours Instant Confirmation
from
$67.65
Details
from
$67.65
Details
Key West Sunset Harbor Cruise
11
...
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2 Hours (approx.)
Best Rate
$75
Details
Best Rate
$75
Details
Top10
Key West Wind & Wine Sunset Sail
52
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running....
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2 Hours (approx.)
Best Rate
$85
Details
Best Rate
$85
Details
Key West Wind & Wine Private Charter
1
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on...
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2.5 Hours (approx.)
Best Rate
$2,500
Details
Best Rate
$2,500
Details
Key West Shore Excursion: Watersports Partyboat
4
Maximize your Key West shore excursion time on a watersport party boat! While your cruise ship is docked at the Key West port, head out...
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6 hours
Details
Details
Key West Full-Day Power Adventure: Sailing & Watersports Package
141
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...
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6 hours Instant Confirmation
from
$169.95
Details
from
$169.95
Details
Top10
Ultimate Adventure
17
Get ready for the water adventure of a lifetime with Fury’s Ultimate Adventure! Reserved for the real water sports enthusiast, this action packed day includes...
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6 hours Instant Confirmation
from
$173
Details
from
$173
Details
Top10
Key West Original Island Jet Ski Tour
153
On our Key West Island Jet Ski Tours you jump on one of our Yamaha Waverunners and cruise around the island on a 28 mile,...
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90 Minutes
~~$150~~
$120
Details
~~$150~~
$120
Details
Key West Conch Tour Train
3
Ride the World Famous Conch Tour Train, the charming and whimsical Key West attraction that has been delighting locals and visitors alike since 1958....
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90 minutes
Best Rate
$31.45
Details
Best Rate
$31.45
Details
Key West Old Town Trolley
149
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...
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1 hour 30 minutes
Best Rate
$47.20
Details
Best Rate
$47.20
Details
Key West Party Boat Fishing Charter
49
Our Key West Party Boat Fishing Charter is the best option for an affordable day on the water with friends, family. Enjoy the best Key...
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6 Hours (approx.)
Best Rate
$66.95
Details
Best Rate
$66.95
Details
Top10
Key West Split Fishing Charter
176
With Key West Split Fishing Charters the overall cost of the charter is split between several people in order to reduce the cost for all....
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4, 6 or 8 Hours
~~$350~~
$175
Details
~~$350~~
$175
Details
Top10
Key West Deep Sea Fishing Charter
50
Experience the thrill of Key West deep sea fishing to the fullest on a hunt for trophy game fish in the open sea with your...
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4, 6 or 8 Hours
~~$900~~
$800
Details
~~$900~~
$800
Details

New Year’s Eve in Key West

Key West Things To Do

Calendar

Key West Attractions

Recommendations

Key West Sunset Cruise

Schooner Appledore Key West Day and Sunset Cruises with Full Bar

Sunset Sip & Sail

Key West Sunset Snorkel Sail

Key West Dolphin Watch Sunset Snorkel Cruise

Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

Key West Sunset Party Cruise

Key West Sunset Champagne Cruise

Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar

Snorkel and Sunset Sail: Rum n’ Reggae

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Sunset Dinner Cruise

Key West Sunset Harbor Cruise

Key West Wind & Wine Sunset Sail

Key West Wind & Wine Private Charter

Key West Shore Excursion: Watersports Partyboat

Key West Full-Day Power Adventure: Sailing & Watersports Package

Ultimate Adventure

Key West Original Island Jet Ski Tour

Key West Conch Tour Train

Key West Old Town Trolley

Key West Party Boat Fishing Charter

Key West Split Fishing Charter

Key West Deep Sea Fishing Charter