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2hr Sunset Sail on When and If

Sunset On A Gorgeous Classic Yacht

When And If is the gorgeous 1939 wooden schooner yacht built by John Alden for General George S. Patton in 1939. Patton declared: “When the war is over, and If I live through it, Bea and I are going to sail her around the world.” The ship’s destiny was never realized due to Patton’s untimely death a few years later, but When And If remained in the family until the 1960s, when she was donated to the Landmark School in Massachusetts. A stint as a much beloved Semester At Sea boat, one nasty wreck, two big rebuilds and many thousands of miles between Nova Scotia and the Caribbean later, When And If has found a winter home in Key West with Sunset Sail Key West.
Well known and feted in the classic boat world and open to the public for the first time in her 81 year history, her owners hope to preserve this stunning piece of American history and beautiful craftsmanship and, perhaps even one day, fulfil her destiny and sail her around the world. Come be part of her story: Help raise sail, take a turn at the helm or relax and enjoy the sailing on Key West’s most historic schooner.

Shared Charter

  • Adult (Ages 13+):$89
  • Child (Ages 3-12):$45
  • Infant (Ages 2 and Under):$25

Private Charters

  • Group of 1-12 People– $2300
  • Group of 13-32 People– $2600


  • Up to 32 Guests
  • All Ages Welcome
  • Children 12 and under must be accompanied by an adult
  • Gratuity not included

Trip Includes:

  • Seats on a shared experience on the schooner When and If with her captain and crew
  • Coolers stocked with ice
  • Bottled water and La Croix
  • A small tasting of two boutique wines made in honor of the boat
  • A gourmet cheese sharing platter

You are welcome to bring any adult beverages of your choice.



Smiling Girl
AGES 3-12:


Baby Boy



2 Hours

We are open for trips daily!