The AYC Foundation Competition Sailing Grant Awarded to Caroline Bayless: Santa Maria Cup International Women's Match Racing Regatta at EYC

Team Something Chill recently returned to Eastport Yacht Club for another stop on the Women’s World Match Racing Tour. After winning the U.S. Match Race Qualifier at EYC just a few weeks earlier and securing a berth to the Prince of Wales Cup, the team was excited to return to Annapolis and build on that momentum.

The team for this event consisted of Caroline Bayless Brown University All-American Class of 2023 (Skipper), Nora Ong Brown University All-American Class of 2023 (Pit and Jib Trim), Katharine Doble Brown University All-American Class of 2026 (Main and Spin Trim), and Piper Holthus Georgetown University All-American Class of 2025 (Bow).

The regatta was sailed in J/22s and featured classic Annapolis conditions. Light and variable winds challenged competitors throughout the event, though most afternoons brought a sea breeze that allowed racing to continue. Race Officer Sandy Grosvenor and the race committee did an outstanding job managing difficult conditions and ensuring competitors completed a high-quality series. Jeff and Sharon Borland and all the EYC volunteers put on a flawless event!

The event began with two challenging round robins. While the team had several extremely close races against some of the world's best match racers, the results did not fall their way. 

Team Something Chill, skippered by Caroline Bayless, had a thrilling run at the Queen of the Castle regatta, fighting their way from 9th place to a final 6th-place finish. This unique ladder format allows lower-ranked teams to advance by repeatedly knocking off the next highest boat. 

Team Something Chill's exciting climb up the leaderboard included the following key matches:

• Race 1: Defeated 10th place Gwynie Dunlevy and her team to begin the climb.

• Race 2: Outsailed the strong 8th place Canadian team, Golonka, in extremely light wind conditions.

• Race 3: Won a very close match against 7th place American team, Cornetta.

• Race 4: Following a penalty for 6th place multi-time Olympic gold medalist Xu and her team during the pre-start, Team Something Chill executed a disciplined and conservative race, capitalizing on the opportunity and securing another victory. 

• Race 5: The final race of the climb was against Megan Thomson, currently ranked third in the world in women's match racing and sitting in fifth overall in the regatta. The team led much of the race and held the advantage until the final downwind leg. Despite a strong effort, and an exciting boat-on-boat battle, Team Something Chill was unable to hold off Thomson and ultimately finished the regatta in 6th place.

"We are incredibly proud of the climb from 9th to 6th against one of the strongest fields in women's match racing. Looking back, the losses in the first two round robins allowed us to reflect upon and cement our mistakes in our minds and learn valuable lessons that directly contributed to our success in the Queen of the Castle. The experience reinforced the importance of adaptability, communication, and execution under pressure."

As the season continues, Team Something Chill is excited to take the lessons learned in Annapolis to their next stop on the Women's World Match Racing Tour in Marstrand, Sweden, in July 2026. The team looks forward to continuing to represent the foundation while competing at the highest levels of their sport.

"We would like to extend our sincere gratitude to the AYCF for its continued support of our team. Competing at events of this caliber would not be possible without the foundation's generosity. The opportunity to race against Olympic medalists, world-ranked competitors, and top international teams is invaluable to our development, and we are deeply appreciative of AYCF's investment in helping us pursue these opportunities."