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Key West Sunset Sail Aboard Legendary Schooner Appledore

Key West Sunset Sail Aboard Legendary Schooner Appledore

Overview

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 passenger schooner. Her decks are spacious and comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.

City: Key West

Thu 05 Jun

Other dates

You can choose the date already on the booking website

Starting at $89.00

Make a reservation

Thu 05 Jun

Starting at $89.00

Make a reservation

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What's Included

Soda/Pop

Chef's selection of Hors d'ouevres and cocktail shrimp

Premium beer, boutique wine, champagne and cocktails for guests >21 years of age

Sunset sail aboard a classic wooden Schooner that has circumnavigated the globe

Additional Info

Service animals allowed
Infants are required to sit on an adult’s lap
Suitable for all physical fitness levels
Total sailing time is 2 hours. There are no stops.

What To Expect

Key West Historic Seaport

The Key West Historic Seaport is a picturesque area located along the waterfront of Key West, Florida. It serves as both a working marina and a vibrant hub for visitors. The seaport features charming old buildings, colorful shops, restaurants, and bars, all set against the backdrop of the sparkling waters of the Gulf of Mexico.

Mallory Square

Mallory Square is a popular waterfront area located in Key West, Florida. It's famous for its vibrant sunset celebration, where locals and visitors gather every evening to enjoy street performances, live music, and food vendors while watching the sunset over the Gulf of Mexico.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (107)

Amy_S

Mar 2025

The crew Josh, Sean and Elliott were wonderful. The Appledore II had lots of good seating and it was wonderful to get out on the water. I would not come to Key West without this on my agenda.

E927WBmelissas

Mar 2025

Amazing so fun great staff Elliot and Andy and the captain were the best really enjoyed this adventure beautiful night great boat would go again and again maybe next time in Maine

F5614NFroberth

Mar 2025

What a beautiful time on the Appledore sunset Cruise. An amazing boat with a great history and certainly a great crew took us out for a wonderful evening on the water off Key West. Captain Pablo along with first mates Brian and Josh made our time outstanding! From the history, hors d'oeuvres and the drinks, including Captain Pablo's own margarita mix, made our voyage one that we will cherish and absolutely take again. Thank you to all involved in the Appledore!