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Sunset Sails Key West

Sunset Sailing Trips In Key West. Schooners, Dinner sails Booze cruises

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Key West Sunset sailing trips

A sunset sailing trip is the perfect way to see the end of a wonderful day here in Key West, Florida. Enjoy a romantic sail into the sunset, or liven it up on one of our Sailing Catamaran Booze Cruises. Sunset Dinner Cruises are also available! We invented sunset. Come see why! 2 hours trips departing just before sunset and returning just after dark. A Key West tradition. Starting at just $39.00 for adults. It is one of the most affordable ways to get on the water and should not be missed.



Wind & Wine SailThe Wind and Wine


Join us for a two hour sunset sail and wine tasting featuring upscale wines and hors d'oeuvres hand picked nightly by the owners. Sail aboard our romantic Skipjack Schooner as we explore the crystal clear waters of the Florida backcountry, enjoy festive music and friends, and look for the world famous green flash of the Key West sunset.

So sit back, relax, enjoy the open bar and sway to the rhythm of the Keys as our crew serve you a nightly selection of: Eight of the finest wines from vineyards around the world, including four reds and four whites. Plus a wide selection of ice cold beer, soft drinks, and bottled water, tasty hors d'oeuvres, breads, gourmet cheeses, crackers, flat breads, summer sausages, fresh fruit, vegetable crudites, and other healthy snacks.

Rated as one of the best sunset cruises in North America by Coastal Living Magazine, Danger Charter’s Wind and Wine Cruise is the ultimate way to kick off an unforgettable night in Key West. Come join the fun today!




$ 95.00 Per person

departure time Vary, according to sunset times and daylight savings. Please call to get the time for your trip. This boat is here in Key West year round.





Sebago Sunset Sail
Catamaran Champagne Sunset Sail

The sun setting over the water of the southernmost point of the U.S. is a spectacular sight! Experience it for yourself while sailing Key West Florida's historic harbor and viewing the Mallory Square sunset celebration from the comfort of one of our beautiful, spacious catamarans. Key West Sebago’s Champagne Sunset Cruise in Key West, Florida includes free Champagne, Beer, Wine, and Soft Drinks.


  Catamaran Sunset Sail Rates
Adults $ 49.00
Upgrades There are upgrades available for beer, wine and high end drinks. Call our office and get more information on these upgrades when you book.

Classic Harbor Line: Key West

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessels in the local schooner fleet: Adirondack III and America 2.0. While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail – a day sail or sunset sail in Key West – is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever. South Florida sightseeing is all about getting on the water, seeing the wildlife, watching the Key West sunset with a loved one, and experiencing the adventure sailing in the great Key West Florida breeze. A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things.


Aboard the Adirondack III

Aboard the America 2.0

Morning Mimosa Sail $ 35.00 Classic Day Sail $ 49.00
Classic Day Sail $ 35.00 Champagne Sunset Sail $ 75.00
Champagne Sunset Sail $ 55.00 Wreckers Race $ 75.00


Schooner Appledore V "Five"Snorkel Sailing

Premium Sailing and Reef Snorkeling aboard the Appledore Five. Experience true sailing and coral reef snorkeling on Sebago's 65" Schooner. Expert snorkel instruction and all the equipment is provided. Lunch is also included with a delicious selection of peel & eat shrimp, fried chicken, Boar's head meats and cheeses, side salads, beers, wine, and much more. This is the premium 5 hour sailing snorkeling adventure.

Sails from 11:00am to 4:00pm

Boarding 10:30

Thursday - Sunday $75.00 per person departing from the Historic Seaport


To Reserve A Key West Sunset Charter Today Call


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The Keys To Key West is a Locally Owned and Operated Company, Members of The Key West Chamber of Commerce.