Sail Key West aboard a 1939 wooden schooner built for General George S. Patton
2 hrs
Captain and crew, wine and beer
Step aboard When And If, a 1939 wooden schooner built for General George S. Patton, for a shared sail with a captain and crew. Help raise the sails, take a turn at the helm, or relax as you take in Key West from the water.
Cancel at least 48 hours before departure for a full refund minus a 10% processing fee. No refund for cancellations within 48 hours. Full refund if the operator cancels, including when weather prevents sailing.
Product ID: DG9T5X
The shared sail requires a minimum of 8 people to sail.
Bring weather-appropriate layers, sunscreen, and a hat. Check the forecast; you may also want a dry bag, change of clothes, and foul-weather gear for the historic schooner sail.
Gratuity for the captain and crew is not included in the listed price. It is customary and appreciated at the end of your sail.
The Perry Marina, 7005 Shrimp Road, Key West, FL 33040
Sailing on the historic schooner When & If is genuinely one of those experiences that surprises people. Built for General George Patton in 1939, the vessel carries real history, and the crew, led by captains like Tyler and Zack, clearly love sharing it. Guests can help raise the sails, take a turn at the wheel, or explore the crew quarters below deck. The vibe is intimate and unhurried, with no blaring music, just wind, waves, and a champagne toast as the sun goes down. The crew consistently earns high praise across the board. Veronica, Yann, Amy, and others are called out by name repeatedly for being warm, knowledgeable, and genuinely enthusiastic about the whole experience. Groups, couples, and families with young kids have all had great times, which speaks to how well the crew reads the room. One reviewer did note a dock location change that wasn't communicated when booking through a third-party platform, so it's worth confirming details directly if you're booking elsewhere. That said, it stands out as an isolated situation in an otherwise overwhelmingly positive pattern of reviews. If a sunset sail is on your Key West list, this one is hard to beat.
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