Sail When And If

Sail When And If Beautiful wooden schooner yacht open for daysails, sunset sails, and private charter. Created in 1939 Come sail with us!
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General George Patton said of his yacht in 1939: "When the war is over, and If I return, Bea and I are going to sail her around the world."

76 years later that dream is still unfulfilled. Now, for the first time in her life, this beautiful sailing vessel has been opened up to the public and put to work to help try and raise money to bring to life the dreams of her designer, her commissioner, her

owner, her captain and her crew. She is a glorious blue-water sailing machine with a destiny to fulfil - Help us make history!

Happy New Year from the crew of the When And If! 📸 cred: Barry Mullin
12/31/2024

Happy New Year from the crew of the When And If!
📸 cred: Barry Mullin

12/22/2024

Happy Holidays from all of us in Key West!

12/14/2024

Thank you for a great video!

We don’t just provide lasting memories. We capture them on film!
12/06/2024

We don’t just provide lasting memories. We capture them on film!

Step back in time and experience the magic of a classic schooner under sail!
12/03/2024

Step back in time and experience the magic of a classic schooner under sail!

All wrapped up and ready to splash and go sailing! ⛵️ 3 cheers🍻 to the crew who knocked it outta the park 🏟️🙏
12/01/2024

All wrapped up and ready to splash and go sailing! ⛵️ 3 cheers🍻 to the crew who knocked it outta the park 🏟️🙏

Last push in she shipyard and we splash on Monday! Book your future sail tonight and get a limited edition When And If ...
11/30/2024

Last push in she shipyard and we splash on Monday! Book your future sail tonight and get a limited edition When And If hat for free!

Black Friday isn’t just for material possessions…. Experiences last a lifetime!
Book your future sail today and receive a free Schooner When And If hat!
Booking link in comments
*free hat for any reservation made before midnight tonight

Not much changes from year to year but we do feel, thanks to all our guests like we are still good custodians for the ol...
11/19/2024

Not much changes from year to year but we do feel, thanks to all our guests like we are still good custodians for the ol’ girl!

What do we have in common?
11/14/2024

What do we have in common?

11/14/2024

Sail with us on our sister ship Schooner Malabar X for a sunset sail while we are in the yard for our annual maintenance for the next few weeks.

You can’t control the wind but you can adjust your sails! We are on our way to Key West for our winter of sailing with ...
11/06/2024

You can’t control the wind but you can adjust your sails! We are on our way to Key West for our winter of sailing with Sunset Sail Key West
Photo cred: Tyler Fields Photography

10/26/2024
Come share an October sail with us in Salem! Sailing through Oct. 31st costumes optional!!
09/27/2024

Come share an October sail with us in Salem! Sailing through Oct. 31st costumes optional!!

When And If will be sailing through October and what better way to embrace the chill than with some warm apple cider and bundled up sailing! 📸 cred Zac

Wonderful pic by M A Barker Photography 🤩
09/06/2024

Wonderful pic by M A Barker Photography 🤩

Huzzah to Schooner Malabar X and our team from Sunset Sail Salem!
09/05/2024

Huzzah to Schooner Malabar X and our team from Sunset Sail Salem!

Come join us for some Sweet September Sailing! Thank you George Bekris for another series of amazing photos!
09/05/2024

Come join us for some Sweet September Sailing! Thank you George Bekris for another series of amazing photos!

Gloucester Schooner Festival this weekend! Join us onboard the When And If for the best views in the race! Only a few s...
08/27/2024

Gloucester Schooner Festival this weekend! Join us onboard the When And If for the best views in the race! Only a few seats remaining for Sunday’s parade and race! Tix link in comments! Photo Credit

Get your tickets to sail with us!!
08/05/2024

Get your tickets to sail with us!!

Start planning your Schooner Festival Weekend NOW! The full schedule is updated on our website and can be seen at MaritimeGloucester.org/sf-visitor-info . The 2024 Program is coming along and we'll make sure you're the first to know when it's ready. What's your favorite event of this unforgettable weekend?

Address

7009 Shrimp Road
Key West, FL
33040

Opening Hours

Monday 8am - 10pm
Tuesday 8am - 10pm
Wednesday 8am - 10pm
Thursday 8am - 10pm
Friday 8am - 10pm
Saturday 8am - 10pm
Sunday 8am - 10pm

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Videos

Sailing in #keywest is an experience not to be missed! Join us Sunset Sail Key West

Sunset Sail in Key West!
Sunset Sail in Key West!

Thank you @perryhotelconcierge for a great video! #keywest #romance #seasonsgreetings #bucketlist

Are you ready to set sail for lasting memories?

Join us as we sail into December in the #flkeys and #keywest

Subscribe to us here on Facebook and let us bring sailing these beauties to life for you! Exclusive content, sailing discounts and being part of living history! Link in comments #subscribe #classicyacht #keywestflorida #sailing.

Destination sailing in tandem with Schooners Malabar X (10) and When And If
Destination sailing in tandem with Schooners Malabar X (10) and When And If

Perfect day in Massachusetts Bay heading for Boothbay, ME in June 2024

Beautiful day for a sail! Hop onboard for a #sunset #sail in #salem today!

June has given us some beautiful weather and we are well on our way to creating some lasting memories for our clients on #salemsound

When And If is back and ready to take you sailing! #sunsetsailsalem We’ve got 4 sails tomorrow all with seats available and we’ve got only a few seats left for our 3:30-5:30 today!

Maintaining the two oldest and most renowned schooners in Key West has its challenges but the rewards are more than worth it!

Sailing through the holidays and into the New Year! Join us for some sweet sailing in paradise!

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