When General (Then colonel) George S. Patton commissioned one of America’s greatest designers to build him a boat in 1939, he had the ultimate ambition in mind:

“When the war is over, and If I live through it, Bea and I are going to sail her around the world.”

The designer, John Alden, had made his name as a builder of elite racing schooners that retained all their beauty and style while constantly winning the premier ocean races of the time. When and If was a new idea: a yacht which would maintain all her classic beauty and hold her own in recreational racing whilst being sturdy, comfortable, safe and luxurious enough to take a family on the voyage of a lifetime.

Long after the General’s untimely death in 1945, When and If sails on. Immaculately and lovingly restored at 76 years old this gorgeous sailing machine stands as a monument to the private ambition of a great war hero and the ingenuity of a great designer – But she is still waiting to realise the dream for which she was conceived.

If you find yourself wanting a terrific view of the famous Key West sunset from the water, you should try the schooner When and If. The people who operate this are fun and lovely.

– Snorkelbeach, January 2016

We sailed the When and If, a unique and beautiful sailboat. It was the highlight of our Key West trip and I highly recommend it!

– Beth S, December 2015


Join us for an authentic sailing experience aboard a wooden schooner that’s been sailing for over 75 years! We have premium sunset cruises every evening, or join us for an day sail out on that Key West water. She’s only in Key West for the winter, so sail aboard this schooner while you have a chance! Read more at

Online Booking for When and If: