Find your perfect adventure
Get $10
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 Luxury Activities, Tours & Attractions

Best Match
Highest 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

191 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
Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

270 ratings
Duration2 Hrs.
If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones, then this is the perfect cruise for you. This Key West Sunset Dinner Cruise allows you to have it all. Experience a delectable dinner and drinks out at sea with a friendly crew and dine on tropical-inspired featured dishes like Roast Pork with heavenly Cuban Bread followed by fried plantains. Your meal is prepared fresh on board and your catamaran features a fully stocked bar and comfortable seating in a climate-controlled cabin. So get out on the water and dine, drink, and dance away the day on this classic Key West Sunset Dinner Cruise.
Read more
from
$80
Experience Today
Seabreeze Dolphin & Snorkel Tour

Seabreeze Dolphin & Snorkel Tour

17 ratings
Duration3.5 Hrs.
Be on the lookout for Key West’s magnificent dolphins while cruising the crystal clear backcountry waters of the Gulf of Mexico. On this family-friendly outing filled with amenities, observe dolphins and other Key West wildlife mingling in their natural habitat among deserted tropical islands. Don't forget to dive in and snorkel Key West's warm, gentle waters to see all the ocean has to offer with a Seabreeze Dolphin & Snorkel Tour.
Read more
from
$99
Experience Today
Private Snorkel and Sunset Sail Excursion

Private Snorkel and Sunset Sail Excursion

40 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
Experience Tomorrow
Private Key West Afternoon Boat Charter (up to 6 guests)

Private Key West Afternoon Boat Charter (up to 6 guests)

6 ratings
Duration3 Hrs.
Climb aboard for a day of ultimate relaxation on this Private Key West Afternoon Boat Charter. Get ready to cruise away on a day to remember where you can do it all. Choose from any or all activities including: Snorkeling, Kayaking, Paddleboarding, Guided Ecotours, Sandbar trips, Family fishing, or just cruising and sightseeing. Totally private and customizable! It’s your day and it can be designed around you and your interests. With no set schedule to adhere to, you may spend as much time doing each activity as you like, just let your Captain know and he will try to make it happen.
Read more
from
$575
per boat
Next Available:
Saturday
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
Experience Today
Ultimate Water Sport Combo Package with Breakfast & Lunch Buffet

Ultimate Water Sport Combo Package with Breakfast & Lunch Buffet

5 ratings
Duration6 Hrs.
Embark on an all day water excursion that includes breakfast, lunch, and unlimited water sports for you and your whole crew with this Ultimate Key West Adventure. Enjoy breakfast from the deck of a spacious 65-foot catamaran as you cruise the Atlantic for a truly incredible reef snorkeling experience. Next, journey into the Gulf of Mexico where you will enjoy a picnic lunch along with your afternoon of banana boat rides, jet skiing, parasailing, and playing on an epic, brand new 3,500 square foot water park. Prepare yourself for good times, food, and fun on this ultimate water sports adventure cruise! Book yours now!
Read more
from
$225
Experience Tomorrow
Seabreeze Sunset Harbor Cruise with Wine and Beer

Seabreeze Sunset Harbor Cruise with Wine and Beer

16 ratings
Duration2 Hrs.
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!
Read more
from
$89
Experience Today
loading
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.