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Are you looking for an exciting alternative to golf or sightseeing for your group? Experience the beauty and excitement of Boston Harbor in a way few people can. 

At the Boston Sailing Center you can charter a single boat with captain, or put your group on a fleet of boats for a relaxing island cruise or an exhilarating regatta.

Whether you are entertaining clients, welcoming others to Boston, or having a company outing, we have the fleet and staff to make your event memorable. Guests can participate as crew, learn basic sailing techniques or just sit back, relax and enjoy the view.

Harbor Cruise

A leisurely, skippered outing that provides guests with a unique view of Boston Harbor and the surrounding islands. Guests can try their hand at trimming the sails and taking the helm or they can just relax and enjoy the view.

Racing Regatta

Regattas offer a friendly element of competition to both new and experienced sailors. We offer two versions - a longer race around one of the Harbor Islands or multiple short course races around buoys set in Boston's Inner Harbor. Both include a briefing on safety and basic sailing, an onboard practice session, and sailing coaches on every boat.

Island Race

This format starts with a briefing on safety and basic sailing held on our upper deck overlooking the harbor. The group then divides into teams and heads to the boats for a practice session with their onboard coach. The boats then jockey for position for the start between the signal boat and the starting mark. Once the starting horn sounds, the fleet heads out around one of the Harbor Islands. If the conditions permit, the instructors will coach the crew on setting the spinnaker for the run back to the finish.

Short Course Racing

For a more intense racing experience, we offer a format with several short races which requires more boat handling by the crews. Each race starts between a signal boat and a starting mark after a 5 minute countdown. The fleet then heads upwind and rounds the windward mark, sets the spinnaker, and heads to the finish line. The regatta winner is the team with the lowest combined score from all the races.

Group Size

"Round the Buoys" Racing events can usually accommodate up to 48 participants with 4 people per boat plus an onboard coach. The other formats can accommodate up to 105 with 4 to 6 people per boat plus skipper. Spectator boats are available allowing for events up to 150 people.


The Boston Sailing Center is available Monday - Friday from 9am to 5pm for corporate charters. Special arrangements may be possible for evening charters.


Take to the water with an experience skipper and hit the race course for a fun filled afternoon of racing or hangback and enjoy a cruise around the Harbor while your skipper does all the work! We believe you will find our prices to be an exceptional deal for an afternoon or evening spent on the water. There is a 2-hour minimum for single boat charters and a 3-hour minimum for multiple boat charters. Half day events range from $140 to $160 per person plus a 15% skipper gratuity. Call or email us for a custom quote at This email address is being protected from spambots. You need JavaScript enabled to view it. 

Upper Deck Rental

The top deck of our permanently docked riverboatThe Merrimack Queen, features beautiful views of Boston Harbor. Spend the day on the water and come back for a post race award ceremony and BBQ. If you just need the space to host your private or corporate party then we have the perfect space for you!