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!

Top10
Key West Wind & Wine Sunset Sail
65
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.) Instant Confirmation
Best Rate
$85
Details
Best Rate
$85
Details
Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar
294
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...
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2 hours Instant Confirmation
~~$74.95~~
$69.95
Details
~~$74.95~~
$69.95
Details
Key West Sunset Harbor Cruise
19
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...
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2 Hours (approx.) Hotel pickup offered Instant Confirmation
~~$75~~
$69
Details
~~$75~~
$69
Details
Key West Sunset Champagne Cruise
89
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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90 minutes (approx.) Instant Confirmation
Best Rate
$49.95
Details
Best Rate
$49.95
Details
Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar
95
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...
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2 hours Instant Confirmation
Best Rate
$99.95
Details
Best Rate
$99.95
Details
Key West Sunset Dinner Cruise
124
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
$79.95
Details
from
$79.95
Details
Key West Glass-Bottom Boat Tour with Sunset Option
103
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
$53.70
Details
from
$53.70
Details
Key West Sunset Snorkel Sail
6
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
$67.54
Details
from
$67.54
Details
Key West Dolphin Watch Sunset Snorkel Cruise
4
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
Snorkel and Sunset Sail: Rum n’ Reggae
27
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
$56.12
Details
from
$56.12
Details
Key West Sunset Party Cruise
107
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
$73.75
Details
from
$73.75
Details
Key West Wind & Wine Private Charter
32
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 Catamaran Dolphin Watch & Sunset Sail
4
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...
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2 hours 30 minutes Instant Confirmation
Best Rate
$109
Details
Best Rate
$109
Details
Sunset Sip & Sail
13
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
$57.54
Details
from
$57.54
Details
Top10
Key West Original Island Jet Ski Tour
246
Enjoy exciting high-speed watersports fun with the best Key West jet ski tour – the Key West Original Island Jet Ski Tour, a guided 28-mile...
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90 Minutes Instant Confirmation
~~$150~~
$119
Details
~~$150~~
$119
Details
Top10
Key West Original Watersports Adventure with Breakfast, Lunch & Drinks
161
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
~~$199.95~~
$174.95
Details
~~$199.95~~
$174.95
Details
Key West Parasailing Adventure
86
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...
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1 hour (approx.) Instant Confirmation
Best Rate
$89.95
Details
Best Rate
$89.95
Details
Key West Conch Tour Train
63
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...
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1 hour 30 minutes
from
$36.70
Details
from
$36.70
Details
Key West Old Town Trolley
166
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
from
$47.20
Details
from
$47.20
Details
Top10
Key West Split Fishing Charter
238
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
71
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~~
$850
Details
~~$900~~
$850
Details
Key West Party Boat Fishing Charter
3
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.) Instant Confirmation
Best Rate
$66.95
Details
Best Rate
$66.95
Details

New Year’s Eve in Key West

Key West Things To Do

Calendar

Key West Attractions

Recommendations

Key West Wind & Wine Sunset Sail

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

Key West Sunset Harbor Cruise

Key West Sunset Champagne Cruise

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

Key West Sunset Dinner Cruise

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Sunset Snorkel Sail

Key West Dolphin Watch Sunset Snorkel Cruise

Snorkel and Sunset Sail: Rum n’ Reggae

Key West Sunset Party Cruise

Key West Wind & Wine Private Charter

Key West Catamaran Dolphin Watch & Sunset Sail

Sunset Sip & Sail

Key West Original Island Jet Ski Tour

Key West Original Watersports Adventure with Breakfast, Lunch & Drinks

Key West Parasailing Adventure

Key West Conch Tour Train

Key West Old Town Trolley

Key West Split Fishing Charter

Key West Deep Sea Fishing Charter

Key West Party Boat Fishing Charter