The Santa Maria Cup puts some of the world's top women sailors head to head in Annapolis. Image: T2PTV Sailing on Demand

Santa Maria Cup Brings International Sailboat Racers to Annapolis

May came in like a lion for the launch of the 2023 Santa Maria Cup, an international women’s match racing event that returned to Annapolis this week for the first time in a decade.

Sponsored by Visit Annapolis and the Eastport Yacht Club, the regatta brings together 10 teams of some of the best women sailors in the world competing in J/22s. They’ll be racing in one-on-one action on the Severn River through Thursday, May 4. 

Match racing is somewhat unique within sailboat racing in that the direct presence of a competitor creates an added game on top of the intensity of standard fleet racing. Boat handling, procedural executions, and crew work must be foregone conclusions as teams use the rules of racing to force their positions, focusing on micro situations for advantage. Match racing might be considered high-speed chess… with some boxing interspersed. 

With 20 knots of westerly breeze and flat water, the real strength of teams was tested as renegade puffs put the boats on their ears and laylines became a bit squiggly. Tacking duels, erratic shifts, forced fouls, and nanosecond leads kept spectators entertained despite the intermittent rain showers. While the rest of the week’s wind forecast looks less aggressive, sailors displayed a ferocity the first day that clearly isn’t going to die with the breeze. 

Sailor Janel Zarkowsky was born and raised in Annapolis, and is currently the assistant sailing coach at Georgetown University. Racing with a team of Hoyas, she finished the day in 9th place. Locals are ready for her to shake off those first-day jitters and dig back into the fight. 

The youngest skipper is Brooke Wilson, just 19 years old and a long way from her home club of the Royal Sydney Yacht Squadron (RSYS). As of Tuesday afternoon Wilson was locked in a three-way tie for first place. She is looking to make a name for herself and her mates, who are all graduates of the RSYS keelboat training program. 

The day’s top two teams are helmed by Swede Anna Ostling and San Francisco Yacht Club’s Nicole Breault. Ostling and Breault are ranked number 2 and 3, respectively, among the world’s best female match racers. When paired on the racecourse together, they seem to tango rather than sail. 

The Santa Maria Cup is the second stop of the Women’s Match Racing Tour, with regattas in San Francisco; Annapolis; Le Havre, France; and Skovshoved, Denmark. The Santa Maria Cup was last held in 2013 and has been resurrected due to the growing popularity of match racing. Some of the past champions include Dawn Riley, Liz Baylis, Sally Barkow, and Anna Tunnicliffe. 

Spectating the event is encouraged off the U.S. Naval Academy seawall or the grounds of Eastport Yacht Club. 

For more information and results, please visit

See highlights of the first day of racing and learn about the Santa Maria Cup in Annapolis in the film below:

Video by T2PTV: Sailing On Demand

-Duffy Perkins