Club Cruises


Our big boat racing and cruising fleet is very active both on the Chesapeake Bay and in New England. We sponsor a Spring and Fall Cruises each year on the Chesapeake. Plus the bi-annual New England summer cruise 

Spring 2024 - Oxford MD (May 23 - 26)
Fall 2024 - Rock Hall, MD (October 3 - 6)

Spring 2025 - St. Michaels, MD (May 22 - 25)
Summer 2025 - Oyster Bay, NY North Shore Long Island to Block Island (July 12 - 20)
Fall 2025 - Annapolis, MD (September 25 - 28)

Spring 2026 - Solomons Island (May 21 - 25)
Fall 2026 - Gibson Island (September 24 - 27)


Our past officers, trustees and members deemed this activity of such importance to the life of the Club that they actually wrote it into the By-Laws. Article 17, Section 2: “At least once in the spring and fall … there shall be a cruise of the Fleet, and all yachts enrolled therein shall be invited to participate.”

The Spring and Fall cruises are a great way for members, guests and newcomers to enjoy the special camaraderie that comes from our common interest and do so in different, exciting venues. Each cruise begins with a “kickoff” onshore welcome reception as boats converge from their various homeports and old friendships are renewed. The final night is brings the awards ceremony and a dinner to toast to the weekend. Trophies are presented not just to those who exhibited their sailing prowess, but also to those who may have demonstrated, perhaps inadvertently, the more humorous side of the sport.

Between the opening and closing ceremonies, yachts usually anchor out, either singly or in large rafts, delighting in being on the water and soaking in the beauty of the surroundings.  Often you’ll see a Stand-Up Paddle Board, Opti or rafts floating amongst the raft-ups.

The days are mostly set aside for yacht races, which often serve the function of moving the fleet from one location to the next. In recent years, The Race Committee has started two classes. All owners are requested to apply for a PHRF of the Chesapeake rating certificate before the cruise. Yachts without a certificate, such as those that have been chartered, are nonetheless encouraged to race.  They are all assigned a rating by the Race Committee. Although we take our racing seriously, we aim to have fun while doing it. Most yachts are sailed by one or two couples or a family, not by a dozen professional racers.

During the Spring Cruise, the first day of racing is the Annual Fun Race for the Happy Hour Trophy. Not only is the race fun and lighthearted, the race instructions can often test one’s wits. This is a great time to shake out the cobwebs that have accumulated amongst the crew during the long winter months.

Although sailing and racing are a highlight of any cruise, many powerboat owners and non-racing owners join the cruises to participate in the parties and raft-ups, and to follow the action on the racecourse. To encourage non-boat owners to come along, a list of charter companies is available. It is a great time for all! For more information please contact the Cruising Fleet Captain, Carolyn Folk at