Sunset Sail Key West

12/14/2024

Congratulations!! She said YES!! @ When And If

12/10/2024

Step aboard and sail away with us! Sail When And If

11/30/2024

Small Business Saturday makes a lot more cents for the local community than Black Friday on Amazon or the likes.
Book your charter today!

11/30/2024

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

11/23/2024

With the wind in the sails and wine in your hand, a classic schooner sunset sail does not disappoint!

11/20/2024

There’s North Wind coming and we love our North Wind Schooner sailing days!

11/19/2024

Shop small businesses this Black Friday sales event! Book now with code BLACKFRIDAYSAIL for 30% off sailing bookings made online or at 305-587-4488 for November.

11/10/2024

Schooner Sailing Season Is Here!
Classic Schooner Sunset Sail: $109 pp
Sailing aboard the Gatsby Era 1930 Schooner Malabar X daily from The Perry Hotel & Marina Key West
Call 305-587-4488 or click the link in comments
Happy Sailing!!

11/06/2024

Tiss the season to book your winter Sailing excursion! Take a look at a day in the life on our most versatile sloop!

Soak up the Sun, Wind and Salt Water with your own private sailing charter in Key West and Stock Island, FL. Come sail like a local. Sunset Sail Key West was...

11/04/2024

Malabar X is ready to take you sailing this Saturday and then every evening for a spectacular sunset sail on one of Americas most iconic schooners! Limited seats available, link in comments.
Photo cred: tylerfields_photography

10/18/2024

Malabar X is on the way!

09/26/2024

Joining us this winter season with daily sunset sails starting Nov. 5th!

https://www.facebook.com/share/nCNwi8WMcz7MLqRY/?mibextid=WC7FNe

Schooner Malabar X 1930, built by Hodgdon Bros in Maine.
John Alden"s final designed and largest schooner for his personal use.
75’ Malabar X competed in the Bermuda Race in 1930, winning her class, and again in 1932, capturing the overall trophy.
Now sailing out of Key West, FL and Salem, MA depending on the season.

Photo by George Bekris

05/10/2024

Only 2 1/2 weeks left to set sail on the When And If before she sails up to sunsetsailsalem for our summer sailing grounds. Get onboard for a memorable sailing experience!

04/29/2024

We are proud to operate such a great vessel and important part of our maritime history!

When And If is a beautiful and historic sailing yacht that holds a special place in the hearts of many sailing enthusiasts. This classic vessel was designed by John G. Alden and built in 1939 for General George S. Patton, the famous World War II general. The yacht's name, When And If, comes from Patton's response to his wife's desire to settle down and live in a permanent home - "When the war is over, and if I return, we will sail together around the world."

The yacht is a 63-foot wooden schooner, with a sleek and elegant design that is a testament to the craftsmanship of its era. It has a rich history, having served in the war effort during World War II and then being used for private cruising after the war. Today, When And If has been restored to its former glory and is used for charter cruises and private events.

One of the most remarkable things about When And If is its enduring legacy and the stories that it holds. From its time as a sail training vessel at the Landmark school to its connection with General Patton, the yacht has a unique history that adds to its allure. It is a living piece of history, a tangible connection to a bygone era of sailing and exploration.

The yacht also represents the timeless appeal of sailing and the sense of adventure that comes with it. Its classic design and graceful lines harken back to a time when sailing was a way of life, and the sea was a boundless frontier waiting to be explored. When And If embodies the spirit of adventure and the thrill of discovery, making it a beloved vessel for those who appreciate the art of sailing.

When And If is a remarkable sailing yacht with a storied past and a timeless appeal. Its connection to General Patton and its rich history make it a cherished piece of maritime heritage. Whether cruising the open seas or hosting private events, the yacht continues to inspire and captivate all who have the pleasure of experiencing its beauty and grace.

04/21/2024

S/V High Tide! Book your private sunset sail and avoid the crowds on Key West’s Premier Charter Sailboat

04/07/2024

Join us on one of our truly historic schooners! We’ve preserved them so that you can enjoy them!

04/05/2024

Such a perfect evening for a sail tonight!! Join us on any one of our fleet of classic boats and take in the sights from the best seats in