The Vineyard Cup Regatta: A Shipshape Addition to Your Summer Itinerary

Sail. Eat. Party. Repeat. That just about sums up the three-day regatta weekend that hits our shores each summer. Whether you’re living the sailor life already or want to root for your favorite schooner, pay homage to the nautical nature of Martha’s Vineyard by experiencing the Vineyard Cup Regatta.


A Summer Event for the Masses: The Vineyard Cup Regatta

Sailboat on the ocean with full sails.


Sailboats, Sailboats Everywhere…But Why?

You expect boats of all sizes in the harbor come summertime, but the July regatta may be the largest collection of sailboats you set eyes on. For more than a decade, the Vineyard Cup Regatta has drawn sailors to Vineyard Haven Harbor to participate in multi-class race courses. Sail Martha’s Vineyard, a local community sailing program, orchestrates the entire weekend to benefit their youth and adult sailing programs, fueling their mission to keep the island’s maritime culture thriving.


But It’s Not Just for Sailors

If you have the skills to captain a sailboat (or know someone who does), set your sights on the Cup and register for an unforgettable experience. For those of us who feel a little seasick at the thought of open water, there’s plenty of socializing and dining to be had on dry land.


Each year, the fun kicks off Thursday night with a scrumptious seafood dinner and auction to benefit Sail Martha’s Vineyard. The following three days are met with the rush of racing ships, full sails, and (eventually) the pop of the winner’s gun. At the end of each race, sailors and spectators come together to celebrate in the Race Village for an after party complete with local food and drink, live music, and the presentation of daily awards.


Weigh Your (Ticket) Options

Are you in it for the full weekend or just looking to get a taste of the sailing atmosphere? Take your pick. Adult passes (for those 21 and older) run $45 a day or $100 for the full three days. If you’re invested in the whole weekend and tempted by the thought of a seafood dinner on opening night, be sure to pick up the Weekend Pass that provides entrance to both.


The Vineyard Cup Regatta is an excellent addition to a smooth-sailing summer itinerary, but it’s just skimming the surface as far as Vineyard events and festivals go. From foodie-favorite chili contests to the Instagrammable Oak Bluffs Illumination Night, give us a ring and we’ll fill you in on all the local happenings you can look forward to during your visit.

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