Santa Maria Cup

June 3 - 6, 2026

Match Racing returns to the Chesapeake Bay!

Eastport Yacht Club

What is the Santa Maria Cup?

The Santa Maria Cup, a premier women's match racing regatta, will return to Annapolis in June 2026, hosted by Eastport Yacht Club. It will feature elite female sailors competing on the Severn River in J/22s. The event, running from June 2–6, includes a double round-robin format followed by knockout stages. This historic regatta celebrates women in sailing and continues its legacy after a successful 2023 revival. Competitors from around the world will participate.

Past competitors in this series include Olympic sailors, Rolex Yachtswomen of the Year, and other international stars of women's sailing. Some past American winners are JJ Isler, Dawn Riley, Julia Trotman, Jody Swanson, Betsy Alison, Cory Sertl, Sally Barkow, and Anna Tunnicliffe. Originally a minor offshoot of the Baltimore Columbus Cup professional match racing regatta series, Santa Maria Cup relocated to Annapolis in 1993 when Eastport Yacht Club (EYC) became the organizing authority.

Where's the best place to view the Santa Maria Cup Women's Match Racing series? 

Watch from shore for full race visibility: The U.S. Naval Academy seawall offers wide views of Annapolis Harbor, the Severn River, and the Chesapeake Bay.

​Head to Greenbury Point for a waterfront vantage point: cross the Naval Academy Bridge to access this scenic nature preserve with multiple viewing spots.

Get on the water for a premium experience: Charter a sailboat or powerboat with friends and family. Local captains can guide you to the best viewing areas for the Santa Maria Cup.

Things to Do

Annapolis has many attractions, museums, restaurants, and shops to keep you busy between races. Choose from waterside dining or a trip to local heritage and historical sites like the Kunta-Kinte Alex Haley Memorial. Or take a tour of the oldest U.S. state capitol in continuous legislative use, dating to 1772, the Maryland State House. Make a day trip to the Arundel Mills entertainment district and enjoy world-class music and touring acts or take your chances at Live! Casino & Hotel. With exciting nightlife, a walkable downtown, and endless charm and waterfront beauty, you are never far from the perfect adventure in Annapolis & Anne Arundel County.

Where should I stay in Annapolis?

Booking a hotel, inn, or bed & breakfast in downtown Annapolis is an excellent choice if you want to stay close to the racing action with easy access to your accommodations. You will find more select and full-service hotels outside downtown Annapolis off Riva Road and West Street. For larger groups, choose from various vacation rentals available in the area. Visit our hotel grid for more information.