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
(95 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
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
916christinaj
Jan 1, 2025
Beautiful! - Stunning sunset on a beautiful, historic boat. The crew was great, and we loved it! I would do it again if I'm ever back in Key West!
Review provided by Tripadvisor
Parke_m
Jan 1, 2025
Historic Sunset Sail - Great experience onboard General Patton’s schooner When and If. Crew was welcoming, knowledgeable, and capable. Highly recommended!!
Review provided by Viator
Helenrj2233wu
Dec 8, 2024
Sunset Cruise on Schooner America 2.0 - Took shuttle bus from out Marriott accommodation to the wharf where this Schooner America 2.0 was located. Hubby the sailor, really wanted to do it so we boarded at 4pm for the Sunset Sail. Staff were a lot of fun and no “granny wings” for those gals hoisting those five heavy sails up. They looked 100 lbs soaking wet and managed to serve all 25-30 guests each with 2-3 drinks, 3-4 side plates of healthy appies in between tacking in 10 knot winds!!! Everyone had a great time and the sunset, called a “green flash” went down in a flash! Wonderful way to mark a visit to Key West and caught the 6:30 bus back to our hotel in perfect timing.
Review provided by Tripadvisor
Clairetu9854lc
Jun 3, 2024
Beautiful Sunset Sail - Beautiful ship with a friendly and fun crew! Everyone on board was so kind, social and they kept the beverages coming! An absolutely beautiful evening with a beautiful sunset view (we also saw some dolphins!) 10/10 would recommend this for anyone visiting Key West!
Review provided by Tripadvisor
Select Date and Tickets
up to 15 guests
1 Adult
February 2025
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Today