Key West Sunset Sail: Historic Schooner Experience

Embark on a historic schooner experience in Key West and set sail into the stunning sunset. Help raise the sail, take the wheel, or simply relax and enjoy the breathtaking views.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Sunset Sail Key West - The vessel is located at the Perry Marina, slip # H16. Find Bad Boys Taqueria, and you’ll spot the Schooner with its polished wooden masts. Check-in and boarding take place directly on the boat, starting 15 minutes before departure.
What's Included
  • Bottled water provided
  • Wine tasting experience
  • On-board restrooms for convenience
  • Beer and wine selection included
  • Champagne upgrade option
What's Not Included
  • Gratuities
Additional Information

Embark on a stunning Key West sunset journey aboard the historic ship When And If! Originally commissioned by Colonel George Patton with the words, ‘Upon the conclusion of the war, and if I make it back, Bea and I will voyage across the globe!’ Stand on the stunning teak surfaces, assist in hoisting the sail, try your hand at the wheel, or simply unwind…

Location
7009 Shrimp Rd
Shrimp Road
We are docked at slip H16 at the Stock Island Marina. Directly in front of the new Sloppy Joe's Dockside bar and restaurant. There is ample free parking. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat.
Cancellation Policy

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

Customer Ratings
4.8
(99 Ratings)
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Forrest
Apr 17, 2025
Thanks for the memories - Fantastically memoriable experience. Crew was Great! Ubered up from Southwinds motel. Easy 20 min ride. Crew met us at the dock and we had beautiful weather. Felt very safe and the sail was smooth.
Review provided by Tripadvisor
Rdewpeck
Apr 9, 2025
Schooner Appledore is the best. - Great experience. Best possible service by crew. Captain and his mates were personable and fun. Cloudy conditions did not do much for sunset but still a great time.
Review provided by Tripadvisor
Lori_m
Apr 3, 2025
Great crew. They made the... - Great crew. They made the trip personal and informative! Beautiful boat and amazing sunset! Highly recommend!
Review provided by Viator
Bradleyf312
Mar 30, 2025
The most perfect evening! - What a perfect evening! My husband and I were looking for a sunset sail to celebrate on our honeymoon and this was exactly what we were hoping for. The crew was exceptional. We loved getting to know them and their experience. The wine was lovely and free-flowing. We loved getting to know the other guests as well. Leaving from Stock Island was very convenient for us as we were staying at a resort a few minutes away. We didn't want a "booze cruise" but a way to fully enjoy a historic sailboat and some lovely views. This was it! We hope to track down the "When and If" at another port in the near future! Thank you all!
Review provided by Tripadvisor
Catherinevp6865zv
Feb 6, 2025
Relaxing schooner ride with beer/wine, knowledgeable crew that encouraged involvement, good conversation with passengers - My mom and I thoroughly enjoyed the schooner ride. The crew was knowledgeable and friendly and took great care of us. There was plenty of space to move around and we were not crowded. The other folks on the schooner were pleasant to chat with, and the schooner itself is beautiful. A wonderful experience that we would book again in an instant!!!
Review provided by Tripadvisor
Brenth201
Feb 4, 2025
Unforgettable experience. - Amazing. Crew was off the charts! Weather was perfect and winds very low. Highly recommend. It's our last day here and it was a perfect way to end our time here
Review provided by Tripadvisor
Ellens640
Jan 15, 2025
Wonderful time! - This is an activity everyone should do! It was so much fun. The crew was absolutely wonderful! They included anyone who wanted to help with the sails or steering. The crew was so friendly and making sure everyone was having a nice time!
Review provided by Tripadvisor
Linda
Jan 11, 2025
Friendly crew - We enjoyed our sunset sail in Key West. Crew was friendly and looked to make it a great night. It was blustery so a choppy and wet sail but we had fun.
Review provided by Tripadvisor
Edwkatz
Jan 4, 2025
Awesome - Fantastic. Tyler and rest of crew were so nice and hospitable. Loved it and would do it again. My family all loved it. Great for kids Edward K, atlanta GA
Review provided by Tripadvisor
David_c
Jan 3, 2025
Key West sunset sail. - A unique and memorable experience. Beautiful vessel with an interesting history. The crew was great!
Review provided by Viator
From $109
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).