Find your perfect adventure
Destination
Experience
Trip dates
Explore
Wish List
Traveler Stories
Blog
LOCAL SUPPORT

Own a Based Fish Mafia NFT?

Save 10% on Your Booking

Key West Sailing Charters

Best Match
Best MatchHighest RatedMost PopularNew to TripShockPrice High to LowPrice Low to High
Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

193 ratings
Duration2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!
Read more
from
$74
Experience Today
Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

94 ratings
Duration1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted sunset fade into dark as the stars give an encore unlike any other. Stretch out and enjoy a pampering of complimentary drinks with family or a special someone. Come feel the ocean breeze blow through your hair and dance across your skin as the sun sets over Key West, book your Champagne Sunset Sail today!
Read more
from
$53
Experience Today
Morning Reef Snorkel and Sail in Key West

Morning Reef Snorkel and Sail in Key West

30 ratings
Duration3 Hrs.
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you. Set off on an adventure and book your Morning Reef Snorkel with Sebago Watersports today.
Read more
from $50
$42
Next Available:
Tuesday
Private Snorkel and Sunset Sail Excursion

Private Snorkel and Sunset Sail Excursion

39 ratings
Duration4 Hrs.
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across the water in classic sail boat before jumping in magical blue waters to snorkel and explore the underwater ecosystems off the coast of Key West. Then wrap it all up with a world famous Key West sunset. The perfect way to spend time with friends and family, book your private snorkel and sunset sail today.
Read more
from
$795
per boat
Next Available:
Tuesday
Key West Sunset Snorkel Cruise

Key West Sunset Snorkel Cruise

55 ratings
Duration3 Hrs.
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!
Read more
from
$50
per boat
Experience Today
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

67 ratings
Duration2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!
Read more
from
$109
Next Available:
Tuesday
Key West Sailing, Kayak, & Dolphin Watching with Breakfast and Lunch

Key West Sailing, Kayak, & Dolphin Watching with Breakfast and Lunch

8 ratings
Duration6 Hrs.
This fun-filled Key West tour combines three awesome adventures into one package. Enjoy a day of sailing, snorkeling, and a grand kayak tour through the mysterious mangrove backcountry. An awe-inspiring eco-tour of glorious Key West, you'll embrace nature in all of her glory as you encounter and observe diverse wildlife on land and under the sea. This all-day adventure includes delicious spreads for both breakfast and lunch, as well as an afternoon snack that is sure to please. Book your Key West adventure today!
Read more
from
$117
Experience Tomorrow
Coral Reef Snorkeling Catamaran Trip with Margaritas included

Coral Reef Snorkeling Catamaran Trip with Margaritas included

8 ratings
Duration3 Hrs.
Experience the best afternoon you'll find on the straits of the Florida Keys by snorkeling this gorgeous coral reef. Climb aboard a luxurious catamaran as you cruise the crystal waters to North America's only living coral reef. Dive into the sparkling, tropical water for an underwater exploration, teeming with brightly colored tropical fish and corals. You don't have to be a jet setter to have a world-class time, so book your trip on this Coral Reef Snorkeling Catamaran Trip with Margaritas included today!
Read more
from
$60
Experience Tomorrow
loading

FREQUENTLY ASKED QUESTIONS

Are Key West sailing charters kid friendly?

Are Key West sailing charters a good date night activity?

Are combination tours available?

Is this a good way to catch the sunset?

What are you expected to see on a Key West sailing charter?

This website uses cookies. Please visit our Privacy Policy to learn how we use cookies and how to control your cookie settings. By clicking or navigating this site you consent to our use of cookies.