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Popular Events

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. 

Whether you seek a relaxing seaside outing, or a serious team building experience, Boston Sailing Center can customize the perfect sailing event for your organization. With forty years of experience on boats ranging from twenty-four to forty feet, Boston Sailing Center is well equipped to satisfy your company’s needs.

Harbor Cruise

This relaxing, skippered outing provides a unique view of Boston Harbor and the surrounding islands for you and your guests. Your team members can try their hand at trimming the sails and taking the helm or they can just relax and enjoy the view. This event works on any of our boats and is a great way to unwind and enjoy the best view of Boston Harbor. 

Around the Islands Race

Regattas offer a friendly element of competition to both new and experienced sailors. 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. 

Group Size

36 Guests Maximum


The Boston Sailing Center is available Monday - Friday from 1pm to 5pm for corporate or private charters. Single boat charters can also be accommodated in the morning or in the evening for a sunset sail. Events requiring six or more boats are restricted to Mondays and Tuesdays. 


Call or email us for updates at This email address is being protected from spambots. You need JavaScript enabled to view it., or submit a quote request below. There is a 2-hour minimum for single boat charters and a 3-hour minimum for multiple boat charters.