Sunset Sail on Historic Schooner: Unforgettable Experience
4.9
40 Ratings
Stock Island
Experience the unforgettable sunset sail on the historic Schooner When And If. Step aboard the 1939 wooden yacht built for General George Patton and sail away in comfort, style, and grace. Relax, unwind, and enjoy the breathtaking Key West sunset.
Duration:
2 hours
Cancellation:
1 day
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Highlights
- 7009 Shrimp Rd - Enjoy a 2 Hr. Sail on a Truly Historic Schooner Yacht. Sip on Complimentary Wine & Beer, Take in the Wind and the Sea on Key West’s Best Sailing Tour
What's Included
- Schooner of wine and select beers included
- Option to upgrade to Champagne
What's Not Included
- Gratuities
Additional Information
Embarking on a journey aboard the historical Schooner When And If is an unforgettable experience! Set foot on the immaculate teak decks of the 1939 wooden Schooner Yacht, constructed for General George Patton prior to the war. Patton named this ship ‘When the war is over and if I live through it, Bea and I are to sail the world.’ Largely used as a private yacht throughout her existence, the When And If is now accessible to the public, offering a chance to relish the sailing elegance, sophistication, and charm of a magnificent classic yacht. Take it easy, sit back, or make a romantic escape as our trained Key West Captain and Crew set off, serve wine, and express their love for sailing, Key West, the ocean, and most importantly… sunsets! Experience relaxation unlike any other Key West Sunset Cruise.
Location
7009 Shrimp Rd
Shrimp Road
We are located on H Dock opposite the Sloppy Joes Dockside Pool at the Perry Hotel. There is ample parking on Marina premises, and it’ll be a short walk to the boat. Please arrive at least 15 minutes prior to your scheduled departure.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(40 Ratings)
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223philippt
May 11, 2024
Best in Key west! - What a great sail!! Capt. Andy and crew were the best! I've been sailing over 30 years and they guys know what they're doing!! Philipp
Review provided by Tripadvisor
Rebecca_c
May 11, 2024
A can't-miss! - This was so much fun! The crew was absolutely phenomenal and went out of their way to make sure we were comfortable. Drinks were provided and nice and cold. The ship was gorgeous. Definitely a highlight of our trip. Thank you for everything!
Review provided by Viator
Wittmeyerj
May 2, 2024
A "better" sunset cruise option - This was a fun trip. The schooner "When and If" is a bit smaller than the typical touristy boats in Key West and feels more comfortable. The captain and crew are good at their jobs and very personable. Also, since the boat is docked on Stock Island versus downtown, it is much easier to access, free parking, and zero traffic to deal with.
Review provided by Tripadvisor
Wdwright0408
Apr 18, 2024
Wonderful Birthday - It was my 70th Birthday and I made the reservation nearly 2 months in advance. The weather was perfect. Captain Andy and crew are the best and made for a most enjoyable two hours. Captain Andy let me pilot a bit and I helped a small amount on a tack. What a most wonderful experience.
Review provided by Tripadvisor
95billr
Apr 9, 2024
Absolutely Perfect! - Just do it. The historical background, the amazing views, and, of course, the AMAZING CAPTAIN AND CREW!!! My wife and I went with two other couples and we now have fantastic memories. Just an absolutely wonderful experience all the way around. Very highly recommended.
Review provided by Tripadvisor
Chestersparks
Apr 1, 2024
Wonderful Wrecker's Race Day on the Water - This is probably my 20th sailing trip with Sunset Sail Key West, and as usual it was a glorious day on the water thanks to the amazing crew and the wonderful historic yacht (When and If). I've also sailed many times on their smaller sailboat (High Tide) when I want a more private experience. Whether it is a day sail, sunset sail or Wrecker's Race, you will always be treated like royalty.
Review provided by Tripadvisor
Kebriggs
Mar 12, 2024
Excellent! - We absolutely loved this sunset sail. The crew, the ship and the sunset… all exceptional.
One disappointing thing - Expedia really messed up and had the tour departure listed at 4:30 instead of 5:30 so we sat around for an extra hour. They did not account for the time change with daylight savings. 😒
Otherwise, a fantastic experience. Highly recommend.
Review provided by Tripadvisor
Barbara_h
Mar 12, 2024
Beautiful experience on When and If - From start to finish, the experience was amazing. The crew was friendly and attentive to all passengers on board. The captain and crew had great communication as well. Can’t say enough about the captain and her expert handling of the schooner, particularly the docking. It was a fabulous experience and will easily be a highlight of our stay in Key West.
Review provided by Viator
Odyssey778039
Feb 21, 2024
If and When we ever come back, would definitely do again! - We were looking for a relaxing, somewhat romantic way to make an unforgettable memory while in Key West. Neither of us had ever been sailing before, and this oneneven has a bit of history, which we both love. You can rent this boat for private tours, but we opted for the "shared" experience (meaning with other people we didn't know previously) because it was significantly less expensive. The entire experience was fantastic. Captain Matt and his crew were friendly and knowledgeable. 10/10bwould do again!
Review provided by Tripadvisor
Ann
Mar 28, 2024
Would definitely recommend! - Absolutely beautiful! Guys were all great and the boat is very cool. There might have been more comfortable seating but actually idk how that would be accomplished.
Review provided by Tripadvisor
