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 English-speaking guide
  • Full open bar for guests over 21
  • Carbonated beverages
  • Bottled water
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
(66 Ratings)
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1 star
Tbird_mike
May 7, 2025
Thanks for a great time! - We enjoyed our schooner outing on the Appledore II and it was fun and relaxing! Our crew (Josh, Andy and Shawn) were very professional and took good care of us! They took the time to visit with us and share some of their experiences and knowledge of the sea. We got to see some dolphins which was an added bonus! We would definitely recommend this experience to others!
Review provided by Tripadvisor
Rachel1957
May 5, 2025
A great experience. - This was a wonderful experience. The crew were all very friendly and informative. We particularly enjoyed chatting with Christina. Drinks were plentiful and the schooner was quiet and peaceful. We saw dolphins and a turtle during our sail - it was a fabulous way to explore the waters off Key West.
Review provided by Tripadvisor
Altman41
May 2, 2025
Great afternoon sail- great crew - highly recommend - Such a great afternoon sailing with Josh , Andy, and Shawn. There were only 7 people on board which really made it special . The boys told us all about the schooner. I highly recommend the afternoon sail . They had a full bar available which was included.
Review provided by Tripadvisor
G4787uschristyb
Apr 28, 2025
Beautiful sail on Appledore on a peaceful Monday - Great day sail on schooner Appledore with Christina, Josh & Sean. They well deserve a gratuity, so be generous for their great service!
Review provided by Tripadvisor
Lindyab
Apr 27, 2025
Golden sun, gentle breezes, excellent crew! - A perfect night with my beautiful daughter and her fiancé. The captain and crew made the sail as special as the sunset itself. Good food, good wine and great conversation! A highlight of my Key West visit! Thanks!
Review provided by Tripadvisor
Heidi_d
Apr 27, 2025
Peaceful! - It was a peaceful and beautiful sail. . Great historical information from Captain! The Crew was super nice!
Review provided by Viator
X6907mtjamied
Apr 22, 2025
Beautiful day for a sail. - What a beautiful day to be out on the water. Josh, Sean, and Elliot were very attentive and the 2 hours just flew by. I will be making this an annual sail.
Review provided by Tripadvisor
Tourist544160
Apr 18, 2025
Best sail in Key West - Great Sail with Pablo, Sean & Brian. Friendly crew, super knowledgable! Very safe, shared lots of history! Beautiful boat highly recommend! Will definitely do it again!
Review provided by Tripadvisor
Steve
Apr 17, 2025
Sailing Excursion - We enjoyed a 2 hour cruise on the schooner. We sited dozens of dolphins and loved the serenity of a quiet and relaxing cruise under sail. Captain Pablo and First Mates Sean and Brian were all professional, friendly, entertaining, and very safety conscious. We would definitely go on an excursion with Schooner Appledore again.
Review provided by Tripadvisor
Teresadm3878lo
Jul 21, 2025
- The captain was extremely uptight (seemed he had no confidence in his crew) even before leaving the dock. Our group did not feel welcomed at all. Don't count on hor d'oeuvres as they are just a nibble. There was a medical issue with one of the guests. We returned early (rightly so) with no apology or fare thee well. Very disappointed.
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).