Schooner Sunset Sail: Key West's Historic Voyage

Sail into history on the Schooner Appledore in Key West. Experience adventure, luxury, and tradition on this unforgettable sunset voyage.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Key West Historic Seaport - The Key West Historic Seaport is a scenic area situated along the waterfront in Key West, Florida. It functions as both an active marina and a lively destination for tourists. The seaport boasts charming historic buildings, vibrant shops, eateries, and bars, all set against the stunning backdrop of the Gulf of Mexico’s…
What's Included
  • Sunset sail aboard a classic wooden Schooner that has circumnavigated the globe
  • Carbonated beverages
  • Alcoholic beverages
  • Snacks
What's Not Included
  • Gratuity
Additional Information

Embark on a sailing adventure in Key West aboard a magnificent 2-masted schooner, reminiscent of 19th-century explorers, while relishing the modern comforts of a contemporary passenger schooner. The decks are both spacious and inviting. With a passenger limit of just 36, there is ample space to move around and enjoy a personal evening experience….

Location
200 William St
William Street
Check-in is located at the far end of William Street, just to the right of the Western Union sign. From Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops. The Marker Resort on your right, and the Schooner Wharf Bar on your left. The booth will be on your left.
Cancellation Policy

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

Customer Ratings
5.0
(215 Ratings)
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Minasf7868mf
Sep 24, 2025
Cotton Candy Sunset - Our Sunset Cruise with Capt Joe & Vitaly was AMAZING! They were very informative & answered all our questions. Great finger foods & beverages made for an enjoyable evening. The cotton candy sunset was the icing on the cake. Highly recommend this tour.
Review provided by Tripadvisor
Rhonda
Sep 11, 2025
Peaceful sunset sail - The sunset sail was amazing. The group size is small, you don't feel crowded and it's peaceful. No loud music, you're able to enjoy the sounds of the sails in the wind and the waves. The female captain and her female first mate (Janet and I forgot the other name!) Were SO friendly, attentive and answered all our questions. The service of drinks and appetizers were perfect. Highly recommend!!!
Review provided by Tripadvisor
Deb
Aug 25, 2025
Excellent Sunset Cruise - We had an amazing sail. The weather was wonderful, fabulous sunset, and the crew took care of our every need. Highly recommend them!
Review provided by Tripadvisor
632renaed
Aug 22, 2025
Wonderful experience - Cannot recommend this enough. If you are looking for a party cruise, this is not it. If you’re looking for a nice, relaxing sail…this is it. It was so peaceful. Absolutely loved this experience. First mate Christina was a great hostess. Both Captain Joe and First mate Christina answered questions and gave info and history.
Review provided by Tripadvisor
Atandsc
Aug 22, 2025
Wonderful sunset sail ! - We’ve tried a lot of the sunset cruises and always end up on the Appledore when bringing first timers. My aunt and uncle had a wonderful sail and the crew was great! The relaxing atmosphere, small number of guests and top notch drinks choices can’t be beat (except by the amazing sunset views!!)
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Tallytripper
May 26, 2025
Great way to end our vacation! - We had a wonderful time and would 100% go on the Appledore again. Both captain and first mate were so friendly and funny. The sail was really peaceful and pretty. The amount of people made it a more intimate evening and we had a good time chatting with the folks on either side of us.
Review provided by Tripadvisor
Bill
May 24, 2025
A perfect sailing experience - My wife and I were aboard the Appledore for a sunset tour last week. Nothing about this trip could have been better. We were not interested in a loud, raucous, party boat sunset ride experience. This is the complete opposite, on a beautiful schooner sail boat, with only 20 other people. Perfect. Drinks and Hors d'oeuvres served. The captain and his mate were friendly, courteous, sailing experts, easy to talk to, and most concerned that each guest experience being the best possible. What a night, and what a great memorable experience. In my mind, no other sunset cruise comes close. Thank you to the Appledore.
Review provided by Tripadvisor
445noras
May 19, 2025
Sunset Romantic Sail - A romantic way to spend an evening in Key West gazing at the sunset with your significant other and/or good friends. A picture perfect experience on this Appledore Schooner starting with a great crew aboard - Captain Joe and First Mate Christina - who both went out of their way to make our sunset sail unforgettable. An intimate laid back evening with great food and drinks, fabulous views and beautiful sailing. Highly recommend to all visiting the Keys!!
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Trav115
May 15, 2025
Amazing Experience, Fantastic Sunset! - The Appledore itself is an amazing ship just to look at, let alone sail in. The ship was very clean and comfortable, the crew were very nice, informative and professional. The cost of a ticket includes delicous snacks and an open bar which was nice. The actual view you get of the sunset is second to none, you really need to watch it from the water at least once. Actually getting to sail in an all wooden boat adds to the cool factor of the experience. Highly recommend this!
Review provided by Tripadvisor
Cruiser12162726039
Sep 11, 2025
Anniversary trip - Staff was great, food and drinks were good too. Wished it would have taken us around Key West instead of straight into the ocean and the very choppy waves. Was difficult to enjoy ourselves as we were holding on for dear life and getting queasy.
Review provided by Tripadvisor
From $89
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).