Sailing heads to Annapolis for annual Kennedy Cup

Kennedy Cup
Nov. 1-2, 2025
Robert Crown Sailing Center
Annapolis, Md.
Hosted by Navy

Results

VALLEJO, Calif. – Following a season full of dinghy regattas, Logan Chapman, Indigo Craig, Owen Cuyler, Chase Englehart, Mateo Krok, Julian Levash, Miles Metoyer Cole Newbrook and Oscar Perry will head to Annapolis, Maryland, to compete in the Cal Maritime's inaugural offshore event of the season.

The Keelhaulers are very familiar with the Kennedy Cup since the program has won the John F. Kennedy Memorial Trophy five times, last winning the regatta during the 2022-23 season. 

If past results offer an indication of the schools competing this year — Navy, Michigan, Wisconsin, College of Charleston (last year's champion) and Rhode Island are a handful of teams that competed in previous events — Cal Maritime will face teams whose student population is exponentially larger by comparison. However, as the regatta's history indicates, the Keelhaulers are one of the teams to beat, despite its size, since it always fields a crew that will take on anyone, anytime, anywhere and consistently punch above its weight — just look at its performances post-COVID.

The warning signal for Saturday and Sunday will take place at 10 and 11 a.m., respectively, with the event's final race starting no later than 2 p.m. on November 2. Even though eight races are scheduled throughout the weekend, only two are needed to deem the regatta official.

Competitors will race Navy 44 MK2 sloops off the Chesapeake Bay off the mouth of the Severn River. 

The Kennedy Cup is one of two offshore events currently on the Keelhaulers' schedule, the other is the Port of Los Angeles Harbor Cup taking place in early March at the Los Angeles Yacht Club in San Pedro, California.