Sail Key West’s Atlantic coast at sunset aboard a historic schooner
2 hrs
Up to 32 people
Captain and crew, wine, beer
Step aboard the schooner When and If, the custom-built yacht once owned by General George S. Patton and preserved for continued sailing. Share an evening on the water off Key West’s Atlantic coast as the captain and crew take you out to catch the breeze.
Help raise a sail, take a turn at the helm, or relax aboard this classic yacht as the sun goes down.
Cancel 48+ hours before departure for a full refund minus a 10% processing fee. No refund within 48 hours. Rescheduled trips are not eligible for compensation. Full refund if the operator cancels, including when weather prevents sailing. No refund if you choose not to sail when the captain deems conditions safe.
Product ID: 2C2U78
Bring sun protection and weather-appropriate layers. It can be cooler on the water after sunset; you may also wish to bring a dry bag, change of clothes, and foul-weather gear.
End of E Dock, Key West Historic Seaport, 202 William St
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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