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Sunset Sail Key West
When and If sunset sail

The schooner sunset·Shared sail on When and If

When and If sunset sail

Two hours at sunset aboard General Patton’s 1939 schooner, from the Historic Seaport downtown.

$109per adult, plus tax. Ages 3–12 $45, under 3 free

When and If was built in 1939 for General George S. Patton, who planned to sail her around the world after the war. Today she takes up to 28 guests out of Key West’s Historic Seaport for the sunset.

The crew raise sail and shut off the engine. Help haul a line, take a turn at the wheel, or sit back with a glass of the boat’s own wine and keep a lookout for dolphins. You’re back at the dock as the sky turns pink.

It’s real sailing, away from the noise of the party boats.

What’s included

  • Two hours under sail with the captain and crew
  • Two boutique wines made for the boat, and select beers
  • Bottled water and La Croix

What to bring

  • Sun protection
  • A layer for after sunset; it’s cooler on the water
  • Flat shoes
When and If

Aboard · Schooner, 1939

When and If

Built for General George S. Patton, who meant to sail her around the world after the war. He never got the chance. Captain Seth oversaw her restoration, then bought her in 2015 to keep her in America.

Built
1939
Built for
Gen. George S. Patton
Length
80 feet
Guests
Up to 28
In Key West
November to May
Read her story

Where you board

  • Historic Seaport

    202 William St, Key West, FL 33040

    High Tide is in front of Schooner Wharf Bar. When and If leaves from the end of E Dock.

    Pay-to-park lot a minute away at 800 Caroline St, or the garage a block away at 300 Grinnell St. Be on the dock 15 minutes before you sail.

    Directions

The schooner sunset

See every sail
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