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
(108 Ratings)
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1 star
Viktar_a
Jan 22, 2026
That was our first... - That was our first experience of travelling at the sail schooner. We were very excited about the trip. Great journey!
Review provided by Viator
Ruth_j
Jan 9, 2026
Great experience. Crew... - Great experience. Crew was great!! Weather was amazing and sailing experience was wonderful. Crew was knowledgeable
Review provided by Viator
Blue700mama
Jan 6, 2026
FUN - The Captain and Mary and Ryan were the best , we had never done anything like that before, they were supper informative about everything that they did with the sails and why. It ended up being one of the most relaxing and fun days with them. Go Vermont!
Review provided by Tripadvisor
Geralyn
Jan 3, 2026
Relaxing, non narrated tour. Great value. - Very relaxing and beautiful. The price is great for a 2 hour tour, compared to the Key West Conch Train being the same price for an hour and a half tour. There is no narration or pointing out of landmarks, just a quiet, relaxing ride. Soda and some alcoholic be erases are included in the price. Great value!
Review provided by Tripadvisor
Z7703bzfredh
Jan 3, 2026
Same boat, different location :) - We took the sunset cruise in May 2025 in Camden, Maine, and decided it would be fun to do another cruise on the same ship in Key West. This time we did the day sail and really enjoyed it. Perfect weather. Attentive crew and we enjoyed talking with the other guests as well.
Review provided by Tripadvisor
John_c
Jan 1, 2026
Awesome time. Would do it again. - Had a great time the crew was very nice and kept your drinks full. Very knowledgeable. Would go on the sailboat again.
Review provided by Viator
Mary_f
Jan 1, 2026
Appledore schooner tour in Key West - Great experience! Friendly tour group and very informative. We really enjoyed it. Felt very safe. Highly recommended.
Review provided by Viator
Kathy_s
Dec 31, 2025
Exciting experience - We took some friends on this adventure on one of the coldest days I’ve ever experienced in Key West, but we still had the best time! The boat is beautiful and th ride, in spite of the rough seas, was very smooth! We did get wet- but we laughed so hard it didn’t matter! Drinks were good and plentiful!
Review provided by Viator
Aaron_h
Dec 26, 2025
Perfect Holiday Activity - Captain Joe and crew Mary/Andy were great! They were very inclusive, letting passengers help raise the sails, and answered questions graciously.
Review provided by Viator
Zzekk38
Dec 25, 2025
Best Sailing in Key West - What an amazing experience. I got to raise the forward sail and we fired a cannon at another schooner! Crew was excellent and very knowledgeable. I couldn’t have asked for a better sailing adventure!
Review provided by Tripadvisor
From $49
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).