
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




