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!

Schooner wine from Hazlitt 1852 Vineyards at sunset? Yes please!!
02/11/2025

Schooner wine from Hazlitt 1852 Vineyards at sunset? Yes please!!

Good morning Harbour Island, Eleuthera! With Schooner Malabar X!
02/04/2025

Good morning Harbour Island, Eleuthera! With Schooner Malabar X!

The sea! The sea! The open sea! The blue, the fresh, the ever free! - Langston Hughes
01/31/2025

The sea! The sea! The open sea! The blue, the fresh, the ever free! - Langston Hughes

If you’re in Key West and you love the When And If, show some of that love! We work hard maintaining this beautiful piec...
01/26/2025

If you’re in Key West and you love the When And If, show some of that love! We work hard maintaining this beautiful piece of history and we need you, your friends, your guests and your support! We don’t ask for donations, we ask you to come sailing with us and experience it first hand. We don’t have the luxury of a dock downtown, we have word of mouth and marketing and the highest upkeep costs of any one of the countless sunset cruises. Join us for a sail and let us know that we are doing this for all the right reasons! Booking link in comments!

I wanted freedom, open air and adventure. I found it on the sea ~Alain Gerbault~
01/25/2025

I wanted freedom, open air and adventure. I found it on the sea ~Alain Gerbault~

Your awaits you in , with us for a truly unique Key West Sunset Sail!
01/23/2025

Your awaits you in , with us for a truly unique Key West Sunset Sail!

Meet the Fleet with Sunset Sail Key West!
01/12/2025

Meet the Fleet with Sunset Sail Key West!

01/11/2025

The sun is shining and the weather is sweet! Makes you wanna…..?

Throwback to Florida Keys Historian Corey Malcom giving our guests some in depth history of the Florida Keys and the imp...
01/09/2025

Throwback to Florida Keys Historian Corey Malcom giving our guests some in depth history of the Florida Keys and the importance that schooners played in our local history! Can’t wait to have him aboard again!

You’ll never work a day in your life if you do what you love!
01/08/2025

You’ll never work a day in your life if you do what you love!

We might be the warmest place in the country yet we’ve been sailing with all our New England sweaters and wool blankets ...
01/08/2025

We might be the warmest place in the country yet we’ve been sailing with all our New England sweaters and wool blankets for our guests.

01/05/2025

It is Schooner weather in Key West!! Break out those new sweaters that your in-laws gave you for Xmas and come out for a sail!

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!

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

It is beautiful sailing weather. Mix that with some boutique wines and champagne and as Mishka says “you’ll never find a sweeter combination!” #keywest #champagne #sunset #historical #bucketlist

The sun is shining and the weather is sweet! Makes you wanna…..?

Did you grow up sailing? These guys are off to a great start!

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

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!

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