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A Celebration of Sailing in Annapolis: Your Guide to the Santa Maria Cup and the Eastport Yacht Club

Maryland’s Maritime History and How Annapolis Became the Country’s Sailing Capital

With its waterside location right at the nexus of the Severn River and Spa Creek, feeding into the larger Chesapeake Bay, maritime life and sailing have always been integral to the character and history of Annapolis. Once a hub of shipbuilding, then becoming a hotspot for seafood procurement and processing (be sure to try some fresh-caught oysters or crabs during your visit), and further establishing its ocean-related reputation with the formation of the US Naval Academy in the mid-19th century, seafaring culture is firmly embedded in our city’s makeup. When you walk down by the City Dock, boats are visible in every direction, coming and going, riding the day’s winds and bringing in the afternoon’s catch. It’s no surprise that Annapolis is known as the “sailing capital of the US,” with groups like the Eastport Yacht Club carrying forward the tradition of sailing and staging events like the Santa Maria Cup, one of the most prestigious and spectator-friendly sailing competitions. From our Annapolis bed and breakfast, you’ll be just minutes away from all the racing action, a front-row seat to the world’s best women’s sailing teams going head-to-head on the beautiful waters off Annapolis Harbor and Eastport Yacht Club.

A fast, sporty, single-masted yacht with three athletes on board

Santa Maria Cup – The Pinnacle of Women’s Competitive Sailing

Set to take place over four days in early spring, the Santa Maria Cup will be the talk of the town and the chat on the water during the racing on April 23-26, 2024. The Eastport Yacht Club first organized the regatta event in 1991, continuing through 2011, then took a hiatus for over a decade before returning triumphantly in 2023. The current iteration of the world-class race is now part of the Women’s World Match Racing Tour, currently the only all-female global sailing competition – formed to give the top women sailing teams an avenue for advancement within the sport. The US has always had a strong presence on the sailing scene, winning the Annapolis event 14 times between 1991 and 2011, while other nations such as Australia, New Zealand, Sweden, Britain, and Denmark are usually vying neck-in-neck for the title. In 2024, Annapolis has the honor of being the first race of the 5-race World Match circuit (which includes subsequent events in San Francisco, France, Sweden, and Denmark), so this year’s regatta will carry extra weight, setting the stage for the winning team to get an early lead in the standings.

Watching the Race and What to Expect

During the four weekdays of the Santa Maria Cup (Tuesday through Friday), races will kick off daily at 9 am, with most of the spectator activity centered around the Eastport Yacht Club grounds (located just a mile from our downtown Annapolis location across the Spa Creek bridge on the opposite side of the harbor from City Dock). As you watch, pay close attention to the all-important race “pre-start,” when the two competing teams on the water tactically maneuver to try and get the best starting position, aiming for both a fast kick-off when the horn blows to start the race and a psychological advantage by leading from the get-go. Like in F2 car races, getting the “pole position” off the starting line is vital, allowing that team to strategize more effectively, holding on to their early lead. 

Bring binoculars, which will enable you to observe the subtle intricacies of how each team harnesses their sails and works the wind, a proper art form. Each boat’s crew has 3-5 members, with one head “skipper” and a supporting cast comprising a trimmer, team racer, and tactician, whose job is to “read” the breezes as they constantly shift. In an instant, the wind can change directions and go from 5 knots to 25 knots, adding an element of surprise throughout the entire race. You’ll also see umpires in separate boats following closely behind the racing teams on the water – keep an eye out for when they raise a “penalty” flag, enforcing the strict rules set forth by the racing committee. The first boat to finish two loops of the course wins that specific heat, with all teams facing each other in the early round-robin phase, followed by the top four teams advancing to the semifinals and the winner taking the prize following the final race between the top two teams left.

Other Events on the Harbor – Friday Night Races, a Lights Parade Like No Other, Boat Tours, Eastport Yacht Club

Although the Santa Maria Cup is sailing spectating at its best, if you visit on other weekends throughout the spring and summer, you can still catch other entertaining sailboat racing events like the Friday Night Beer Can Series. Eastport Yacht Club puts on these more amateur-friendly and low-key races on several Fridays in 2024 – May 17 and 31st; June 7, 14, and 21st; July 12, 19, and 26th; and August 9 and 23rd. They also organize the annual Lights Parade during the holiday season, a beloved Annapolis holiday tradition and one of the most unique Christmas parades you’ll ever see, with boats decked out in bright lights cruising along the harbor as festive crowds gather to watch them pass by. 

If watching all the sailing inspires an urge to get out on the water, hop aboard the Harbor Queen guided boat tour, which starts running from City Dock in mid-March and continues through the busy summer season. Even better, make a reservation on the Harbor Queen during the Santa Maria Cup competition week, getting up-close views of the race course from out on the beautiful expanse of the Severn River.

Stay with us – where the Eastport Yacht Club is just a mile away, with excellent views of all the excitement, close competition, and thrilling racing of the Santa Maria Cup!

Boats in the Harbor in Annapolis