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Sunset Sail Key West Presents: The Schooner When And If

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.”

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.

Sailing on When And If

Private Charter

Private charters aboard When and If are a thing apart from the humdrum of life ashore. Take command of this magnificent vessel as your captain and crew sail you away for … A 2 hour daysail? A sunset experience? A day’s snorkel adventure? A week cruising the Keys? You decide!

Private Charters Include:

  • Complimentary shuttle pick-up and drop-off
  • Free Parking
  • Complimentary ice, bottled water, San Pellegrino and La Croix
  • Catering available by prior appointment
  • Use of snorkel gear by prior arrangement

A Shared Sailing Trip

We love sharing our boat with as many people as we can! Sail away on this magnificent ship with other guests on a shared experience: A 2 hour daysail to soak up the Florida sun, or that Key West must-do – a 2 hour sunset sail. Book your spots early to avoid disappointment!

Sailing trips include:

  • Complimentary shuttle pick-up and drop-off
  • Free Parking
  • Complimentary ice, bottled water and La Croix – BYOB!
  • Gourmet cheese sharing platter (Sunset Only)

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