Any sail onboard the historic Schooner When And If is a memory of a lifetime!
Step aboard the beautiful teak decks of the 1939 wooden Schooner Yacht built for General George Patton before the war. The Ship was named by Patton "When the war is over and if I live through it, Bea and I are to sail the world"
Loved and enjoyed as a private yacht for much of her life, When And If is open to the Public to Enjoy the Sailing Comfort, Style and Grace of a superb classic yacht.
Sit Back, Relax or Romance the sail away as our experienced Key West Captain and Crew set sail, pour wine and share their passion of sailing, Key West, the sea and best of all.... Sunsets!
Sail and Unwind Like No Other Key West Sunset Cruise
Posted By : K5891YZwilliaml
Awesome crew and schooner (with a great history)! The sailing was great and the sunset was glorious with a great moon rising on the way back. This is a MUST GO cruise!
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Posted On : 2024-06-09 03:22:17 
Posted By : mkirby01
My friends and I visited Key West for a girls’ trip. We chose the “When and If” for a sunset sail on our last night. It was perfect! The crew was friendly and accommodating. The boat was beautiful and historic. I usually get seasick; however the sail was perfectly smooth. I never felt the tiniest bit of sickness. We enjoyed a beautiful sunset cruise with complimentary wine. I highly recommend this sunset sail!
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Posted On : 2024-06-07 23:38:12
Posted By : 223philippt
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
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Posted On : 2024-05-11 20:59:21
Posted By : Rebecca_C
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!
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Posted On : 2024-05-11 09:10:17 
Posted By : wittmeyerj
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.
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Posted On : 2024-05-02 10:29:31
Posted By : wdwright0408
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.
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Posted On : 2024-04-18 07:41:43
Posted By : 95billr
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.
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Posted On : 2024-04-09 08:11:00
Posted By : chestersparks
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.
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Posted On : 2024-04-01 17:04:50
Posted By : Ann K
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.
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Posted On : 2024-03-28 21:12:24
Posted By : kebriggs
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.
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Posted On : 2024-03-12 22:46:13
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