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
(251 Ratings)
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Paulmh356qs
Jan 17, 2026
Romantic relaxing sunset cruise out of key West. - Highly recommended sunset cruise out of Key West aboard the schooner Appledore. Captain Shawn and his two crew members were very welcoming and attentive. Wonderful experience to help celebrate my wife’s 50th birthday trip. Would highly recommend this cruise and plan on booking again when we can bring the whole family down.
Review provided by Tripadvisor
Heather_m
Jan 12, 2026
Relaxing! - Most relaxing sunset cruise I've ever been on. Love that it was a small group with more that adequate seating and no soundtrack playing to detract from the experience. It was great to visit with the crew, who took excellent care of everyone on board. And actually being under sail for the majority of the trip made for a memorable time. Would definitely recommend and do again!
Review provided by Viator
Joanieb360
Jan 9, 2026
great fun and great crew - The day was perfect! Three person crew, Sean, Mikey and Andy are knowledgable and gun. Upscale hors duevres and drinks!
Review provided by Tripadvisor
Compass38009952072
Jan 9, 2026
Great trip - Great trip. Polite crew. Delicious hors d’ouvres. We highly recommend this trip on an authentic old schooner, we got some pretty good shots of the sunset despite the threatening clouds
Review provided by Tripadvisor
Yana_l
Jan 7, 2026
It was an absolutely... - It was an absolutely fantastic experience and the crew (Christina and Ryan) and captain Josh were great. We enjoyed three tasty apps and a mini key lime pie as a desert. Note that there is a premium upcharge for some cocktails but "basic" stuff is included and I was very happy with my G&T. Note: even when Viator offers an option to add the reservation to your mobile wallet, you still need to obtain a pass tin order to board (the pass is obtained at the kiosk just outside where you board). And be on time (which is at least 30 min early)! One couple arrived a few minutes late and did not board. Overall, I highly recommend this experience.
Review provided by Viator
680venetiar
Jan 5, 2026
Peaceful moments in paradise - Relaxing sunset listening to good music, water flowing by, and friendly chatter of quality people. Yummy bites and drinks. Overall, a very good experience.
Review provided by Tripadvisor
Kath
Jan 4, 2026
Best sailing ever! - Best Sunset Sail Ever! Capt Sandy & Mate Vitali provided for a super successful Sunset Sail with entertaining moments & astounding sailing knowledge along with wonderful catered food & assorted drinks while cruising to our Fantastic Sunset! I believe they even had something to do with the perfect weather we had that night! A shout out to Melissa at Checkin who wa very helpful! Thanks Everyone, I’ll be back!
Review provided by Tripadvisor
C9530lulisat
Jan 2, 2026
Perfect - Excellent. I think they limit the group to 36 people which was perfect. Staff and sail were outstanding . Light cocktails and appetizers were complimentary. Absolutely no issues. It was perfect. This isn’t a party sail. If you want that vibe, go elsewhere. We booked ahead, but I think you can try to book day of near the boat. Everybody involved from captain to deckhands were exceptional.
Review provided by Tripadvisor
Cynabarr51
Jan 2, 2026
Great way to see the sunset - Very lovely evening sunset sail. Crew were friendly and knowledgable. We had great weather and calm waters Lots of fun. Snacks were a nice treat. Better views if you sit on the outer sides of the ship, not in the middle and more to the rear
Review provided by Tripadvisor
2024florida
Dec 31, 2025
Great sunset trip - Experienced crew, polite and efficient. We enjoyed our trip from Key West to watch the sunset. Adult beverages were offered throughout the trip
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).