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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 12 Feb

Other dates

You can choose the date already on the booking website

Starting at $89.00

Make a reservation

Thu 12 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)

annolev

Dec 2024

Compared to the other sunset cruise selections, this one is fabulous! The range of beverages that are included plus the food that is included can’t be beat! Who doesn’t love a shrimp cocktail at sunset? The captain and crew are amazing and know what they’re doing. The trip was incredibly enjoyable.

Response from Host

Dec 2024

Thank you for your wonderful review! We’re so happy to hear you enjoyed the sunset cruise and found it to be a standout experience. Shrimp cocktail at sunset really does hit the spot, doesn’t it? 🌅🍤 Our captain and crew take pride in making every trip memorable, and we’re thrilled you had such a great time. We hope to welcome you back aboard for another fabulous adventure soon!

Voyager48807225491

Dec 2024

What a treat! Captain Pablo kept us riveted with Key West and Appledore history tales as Luke and Shawn kept the sails trimmed and took good care of us with drinks, great appetizers, and a key lime tart. There may have even been an exchange of cannon fire from local pirates :). I lived aboard the Appledore for a semester when it was giving Long Island University Marine Biology students real-life field experiences as we sailed from New York to the Virgin Islands back in the 1980s. It was so fun to give my family a taste of sailing life as we joined the schooner for a lovely sunset cruise - a wonderful way to spend an evening! This was the highlight of our Keys trip, and I bet it will be yours, too. Next time: a reunion with SEAmester buddies?

Response from Host

Dec 2024

"Thank you for sharing such a heartfelt and nostalgic review! We’re honored to have been part of your Keys adventure and thrilled to hear Captain Pablo’s stories, along with Luke and Sean's hospitality, made the evening so memorable. It’s incredible to hear about your time aboard the Appledore in the 1980s—it’s a privilege to reconnect with someone who has a personal history with the schooner! We’re delighted that your family got to experience a taste of sailing life, complete with a bit of playful pirate action. Until next time, fair winds and following seas!"

randyb986

Dec 2024

Great sunset cruise. Wonderful deckhands and captain. Would highly recommend this cruise don’t hesitate to book, you can’t go wrong.