Step aboard for Key West's most infamous race.
The 2026 Wrecker's Race is here.
Secure your spot for Key West's most infamous race.
The 2026 Wrecker's Race is here.
January 25th @ 11AM
.svg)
click to hear the wind & sea
.jpg)
Yes, it was!
Built in 1939 for General George S. Patton, "When And If" was commissioned by Patton himself from naval architect John Alden, and built by FF Pendleton in Wiscasset, ME to sail around the world “When the war is over, and If I live through it.”
Unfortunately, he never got the chance to sail aboard her.
Fortunately, you do.
The Wrecker's Race lasts approximately 4 1/2 hours and departs from the Perry Marina.
Here is our itinerary!
10:45 AM – Boarding Begins: Guests are welcomed aboard 15 minutes prior to departure. Meet the crew, settle in, and enjoy the anticipation as we prepare to set sail.
11:00 AM – Departure: Lines are cast off as we set sail toward Key West Harbor, beginning our journey into the heart of the regatta.
12:00 PM – Lunch & Harbor Sail: Enjoy freshly made, delicious sandwiches while sailing through historic Key West Harbor. Around us, regatta vessels begin to gather—classic schooners and sailing yachts assembling for one of the most exciting maritime spectacles in the Keys.
12:45 PM – Pre-Race Action: The intensity builds as boats maneuver for position near the start line. Watch skilled crews jockey for advantage, sails trimmed and eyes fixed on the wind.
1:00 PM – Race Start: Engines off. The Wreckers Cup officially begins from a start line due west of Fort Zachary Taylor State Park. Under sail alone, vessels race westward—just as the wreckers once did—relying purely on wind, tactics, and seamanship.
The Race - The one-way course runs to a finish line due west of Sand Key Lighthouse, approximately 6.8 nautical miles SSW of Key West. Race duration varies from 45 minutes to 2 hours, depending on wind speed and direction.
Finish Line – Celebration at Sea: Cheers erupt as boats cross the line and acknowledge the race committee. Crews and guests celebrate completing a historic reenactment—honoring the brave wreckers who once raced to recover and assist vessels stricken on the coral reefs.
Return Sail – Stock Island Bound: A scenic 7-nautical-mile motor/sail back toward Stock Island offers time to relax, reflect, and relive the highlights of the race. Complimentary beer and exclusive Schooner Wine are served as we toast a regatta well raced.
3:30–4:00 PM – Return & Disembark: Arrival back at The Perry Marina. Guests disembark after experiencing a truly unique and storied Key West maritime tradition—one rooted in history, competition, and the enduring spirit of sail.
We might be biased, but we would make them now. Waiting until the last minute can leave you out of luck, considering we sell out quickly.
You can book easily online here.
Yes! That's one of the advantages of leaving from the Perry Marina. Parking is free and only steps from the boat itself.
2 distinct wines have been created to celebrate sailing on the When and If.
Both of which you can enjoy during your sunset sail.
Red: A cabernet blend akin to the reds from Provence, France. Not too heavy, not too light. Just right to enjoy on the water.
White: Similar to a balanced chardonnay that is light, crisp, and not too buttery or heavy on the oak.
We board 15 minutes before departure time. So you're best to arrive at the Perry Marina 30 minutes before departure time so you won't be rushed for parking.
You can! We have a ship's store with everything from shirts to mugs and hats.
