Key West Sailing: 19th Century Schooner Adventure

Sail Key West on a 2-masted schooner, enjoy a full bar, and steer the ship. Experience 19th-century adventure with modern comfort.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Mallory Square - Mallory Square is a well-known waterfront destination in Key West, Florida. It is renowned for its lively sunset celebration, where both locals and tourists gather each evening to enjoy street performances, live music, and food vendors while witnessing the sunset over the Gulf of Mexico. The square is encircled by historic…
What's Included
  • In-person Guide: English
  • Carbonated beverages
  • Bottled water
  • Alcoholic beverages
What's Not Included
  • Gratuity
Additional Information

Sail through Key West aboard a magnificent 2-masted schooner, reminiscent of 19th-century explorers, while indulging in the modern comforts of a contemporary passenger schooner. The decks are roomy and inviting. Experience the thrill as the crew raises the sails. Join in this timeless tradition by assisting in hoisting the sails. Steer the ship and…

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
4.9
(113 Ratings)
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Darrenv289
Mar 24, 2026
Appledore day cruse is awesome, great crew - The crew was great, Kelly, Andy and Cristina were the best and made the trip. This is the 4th time I have sailed on the Appledore in Key West I do it every time we are in the Keys. We are talking about doing it multiple times next time we are in the Keys since we enjoy it so much.
Review provided by Tripadvisor
Karen_d
Mar 23, 2026
On the water in Paradise - Wonderful sailing weather. Kelly, Christina and Brian were absolutely awesome. They answered any and all questions in depth. Great crew!! Will be sailing with them again
Review provided by Viator
Xxx057
Mar 16, 2026
Excellent !!! - A fantastic day out. Crew were superb from start to finish. We would highly recommend this excursion. Difficult to fault anything. Give it a go, a great experience.
Review provided by Tripadvisor
874dennyl
Mar 11, 2026
Great Crew, Great Sail - My wife and I had a wonderfull time on this afternoon sail. Great, friendly captain and crew. We would highly recommend the Appledore!
Review provided by Tripadvisor
Jerryhf553va
Mar 11, 2026
Schnooner fun - Outstanding sail with Captain Kelly and crew(Andy, Christina, and sales agent Melissa). Explained how the schnooner and big sails work on the big water. And a cocktail in sunny Key West. Go Kelly!
Review provided by Tripadvisor
Stewart_t
Mar 11, 2026
Ahoy Mates - Perfect amount of time on the water with the unique experience of sailing. Amazing value with a couple drinks! Incredible staff, sailors and last but not least, bar tenders. Great Bloody Marys! They do it all very impressively. Thanks for a great couple hours.
Review provided by Viator
S9320hyalicec
Mar 11, 2026
So pleasant and relaxing. - Great crew, nice sailing partners on Tuesday afternoon. Felt like I was out with friends. High marks on all fronts .
Review provided by Tripadvisor
Jenniferhy4439wi
Mar 11, 2026
Outstanding sailing on the Appledore II Key West - Captain Kelly, her crew Andy and Christina gave us an unforgettable day on the gorgeous water with a great breeze for sailing. The journey was highlighted with their careful explanation about the schooner and with explanations about sailing. We also had a great experience checking in with Melissa Pearson who helped us hit the deck on time. We highly recommend this cruise on the Appledore II
Review provided by Tripadvisor
W315qwterriw
Mar 7, 2026
Amazing and beautiful ship - We were told about this exact vessel by a bartender at the beach and said we would have the most amazing experience. The crew was phenomenal. Christina and Mary and the captain were top notch. Highly suggest this trip
Review provided by Tripadvisor
Jankees_m
Apr 1, 2026
The tour was canceled by... - The tour was canceled by the tour company an hour before it was supposed to start, because they did not have enough participants.
Review provided by Viator
From $49
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).