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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

Mon 16 Feb

Other dates

You can choose the date already on the booking website

Starting at $89.00

Make a reservation

Mon 16 Feb

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)

161russelld

Mar 2025

We had an excellent sunset cruise for my wife's birthday. Great experience watching the crew raise and lower the sails. Captain and crew provided a great cruise.

X3507MGkatieg

Mar 2025

First timers! Sailing on the Appledore was so much fun! We were hesitant thinking it was going to be a long 2 hours because the average age of other passengers was definitely 65+. No worries though, we had a great time! The scenery was beautiful and sailing on the water was enjoyable. The crew were happy to interact with guests and let passengers help put up sails. My husband even got to spend time steering the ship! Captain Pablo was happy to chat with us and we learned a lot about so many different things. Andy and Luke were also fun to talk to and hear their stories about maritime life. Refreshments were tasty, and we were fully immersed in maritime life ending the trip by firing a cannon on a neighboring vessel as we headed back to port. One member of our party was slightly disappointed he could not climb the rigging and use a line to swing off the ship. Overall, fantastic experience!

angelamX7765DP

Mar 2025

Mixed feelings: trip was good. But leaving an old man behind cause he was “late” but leaving 5 min early was just ugly and overshadowed my experience.