

A Key West Sailing Tradition!
January 25th, 2026
February 22rd, 2026
March 29th, 2026
April 26th, 2026
Join in the “day of wreckoning” aboard Sebago’s Appledore II Schooner as we race the 7 miles to Sand Key. In days of old, many ships grounded on the dangerous reefs off of Key West. The first wrecking captain to reach the stranded boat was awarded salvage rights. With wrecks happening once a week, this made Key West one of the wealthiest cities in the United States. Competition was fierce and spirited among Key West’s captains.
Today, competition is just as intense in the Wrecker’s Race with the prize being annual bragging rights to the fastest ship. A unique adventure unlike anything else you have experienced, this fun escapade will be a highlight of your Key West vacation!
Leaves from our Key West Historic Seaport location.
This event has limited availability and will sell out quickly.
Only 49 passengers for an intimate sail
You Will Be Sailing On Appledore II, A Two-Masted 86′ Windjammer
Boarding Starts 1/2 Hour Before. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.
Wide decks with room to walk around
Generous seating
Race crew lunch, premium beer, boutique wine, sangria and soft drinks!
A spacious head (bathroom)
Grab your hat, sunglasses, camera and love of adventure. We will do the rest!
Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age.