Schooner Wharf Bar Wrecker’s Cup Race Series 2026
Experience the Annual Wrecker’s Cup Race a Key West Sailing Tradition!
Inspired by Key West’s colorful maritime past, the Wrecker’s Cup Race brings history to life with one of the island’s most exciting on-the-water events. In the 1800s, ships often ran aground on nearby reefs, triggering fast-paced races as crews hurried to reach the wreck first and claim salvage rights. Today’s race reimagines that competitive spirit—minus the piracy—into a thrilling boat race that draws spectators and participants alike.
For visitors, the Wrecker’s Cup offers a rare chance to witness Key West’s seafaring heritage in action. Boats race at full throttle, crowds line the harbor, and the atmosphere feels distinctly island-authentic. The prize may now be bragging rights rather than cargo, but the intensity and excitement remain just as strong.
The race departs from the Key West Historic Seaport.
What’s included
- Complimentary lunch and 2 rounds of beer, wine, or champagne of your choice!
- Soft drinks and water always included
- A boxed lunch provided by Key West locals’ favorite Old Town Bakery
- A fast-paced and exciting race nine miles offshore into open water culminating in the rounding of the famed Sand Key Lighthouse
- Iconic 360* views of Mallory Square, Fort Zachary Taylor, and Sunset Pier.
- Ocean wildlife: keep your eyes peeled for dolphins, sea turtles, and waterbirds
Highlights
- Approximately 3-hour Key West sailing adventure
- Tickets include a delicious sandwich from Old Town Bakery, chips, pasta salad, and dessert
- Adult tickets include two rounds of beer, wine, or champagne (soft drinks and water are always included!)
- Additional drinks and snacks available for purchase
- The boat will depart at 12:30 pm but the race officially begins at 1 pm and we typically return at 3:30. Suggest being 30+ minutes before departure
Schooner Wharf Bar Wrecker’s Cup Race Series FAQs
Does the Wrecker’s Race sell out frequently?
Yes, the Wrecker’s Cup Race is a popular event.
Is there parking, where? And how much is it?
Parking in Key West is very limited. There is a local municipal parking lot at the corner of Caroline Street and Margaret Street, very close to our ticket booth where you check in! Further information will be provided upon purchasing your tickets.
Is food served during the sails and what is it?
Yes! A gourmet sandwich, pasta salad, fruit salad, cookies and chips from a local Key West deli!
Is there a bathroom on the boat?
Yes, the boat is equipped with two bathrooms that are accessible at all times. We call them “marine heads” and they are very easy to use! The Captain will give directions on their use once you are on board.
What should I wear on the Wrecker’s Race Sail?
For our day sail, we recommend wearing comfortable clothing and footwear (high heels are not recommended). Feel free to come in a bathing suit, but bring a light jacket just in case! And don’t forget your sunscreen and sunglasses!
Where does the sail finish?
Our Wrecker’s Race trip starts and ends at Schooner Wharf.
Is gratuity included in the price of the sail?
Gratuity is not included in the price of the sail. It is customary to show your crew appreciation for their hard work with cash tips following the trip.
