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Sunset Sail Key West
Rosé All Day sail

A day under sail·Shared sail on When and If

Rosé All Day sail

An afternoon on General Patton’s 1939 schooner, glass in hand, from the Historic Seaport downtown.

$75per adult, plus tax. Ages 3–12 $39, under 3 free

Two hours of afternoon sailing aboard When and If, the wooden schooner built in 1939 for General George S. Patton. Help raise sail, take a turn at the helm, or settle in with a glass of the boat’s own wine and enjoy the sights and sounds of Key West from the water.

The sail goes with 8 guests or more. To be sure of your sail, book all 8 places, and we refund the extra places as other guests sign up.

What’s included

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

What to bring

  • Sun protection
  • 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

A day under sail

See every sail
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