THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Step aboard Boston Sailing Tours’ 6-hour charter to Grape, Lovells, and Bumpkin Islands for a secluded day of sailing, wildlife, and historic island trails just minutes from downtown Boston.
Step aboard Boston Sailing Tours’ 6-hour charter to Grape, Lovells, and Bumpkin Islands for a secluded day of sailing, wildlife, and historic island trails just minutes from downtown Boston.
Book with Boston Sailing Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Boston Sailing Tours · Boston, Massachusetts
Boston’s harbor bustles with energy, but just beyond its skyline lie islands where time slows and nature holds sway. Boston Sailing Tours offers an exclusive 6-hour sailing adventure to Grape, Lovells, and Bumpkin Islands—three relatively isolated outposts that aren’t accessible by public ferries. Departing from Courthouse Docks at 2 Northern Ave, this journey combines the thrill of open-water sailing with the intimacy of private island discovery, making it a standout among coastal adventures in the region.
During the trip, the Francesca—the comfortable sailboat captained by seasoned mariners—navigates the cool, sparkling waters of the Boston Harbor Islands National Recreation Area. Passengers disembark to roam unspoiled beaches, hike old trails, and absorb sweeping views of the Atlantic. These islands serve as quiet refuges for diverse seabirds and small mammals, while weathered military installations whisper stories from the Revolutionary War through World War II, offering a tangible link to New England’s coastal defense history.
What sets this experience apart is the freedom to pack your own food and drinks, turning your day into a personalized picnic afloat and ashore. The islands receive few visitors annually, meaning you’ll likely enjoy significant stretches of solitude amid coastal pines and rocky shorelines. Boston Sailing Tours prides itself on providing an authentic maritime adventure rooted in local geography and history, with expert guidance to ensure comfortable, safe travel.
Whether you’re seeking a family outing, a unique day trip with friends, or a chance to disconnect from the city, this sailing charter delivers a balanced blend of recreation, education, and rare landscape encounters. It’s a singular way to engage with Boston’s maritime environment beyond the usual tourist paths.
easy.
6 hours.
Suitable for all fitness levels; requires basic mobility for boarding and walking uneven island terrain.
Yes, guests are encouraged to bring easy-to-eat snacks and drinks, including beer or wine in cans or bottles. Hard liquor and red wine are not allowed.
Boston Sailing Tours provides USCG-approved life jackets for all guests, with children under 12 required by law to wear one.
No experience is needed; the crew manages the vessel while you enjoy the journey and island visits.
If the tour is canceled due to weather, you may reschedule or receive a refund minus a 10% fee.
Pets are not permitted aboard the Francesca or on the islands to protect wildlife and maintain safety.
The boat departs from Courthouse Docks at 2 Northern Ave, Boston, with paid public parking nearby.
The islands served as key defensive points from the Revolutionary War through World War II, with visible remains of old fortifications and gun emplacements.
Boston Sailing Tours supports responsible tourism by limiting visitors on the islands and promoting Leave No Trace principles to protect delicate habitats.
Boston Sailing Tours operates sailing excursions out of Boston, Massachusetts, offering a range of guided and hands-on experiences on Boston Harbor. The company runs three primary trips: a 4-hour "Half-Day Sail Around The Islands" departing from Courthouse Docks that sails along the New England coastline and past historic stone fortresses; a flexible "2-Hour Day/Sunset/Night Sail" for short scenic cruises that showcase landmarks like the USS Constitution and Castle Island; and a 6-hour "Full Day Sailing & Island Experience" that visits Grape, Lovells, and Bumpkin Islands with time ashore to explore beaches, wildlife, and military remnants. All advertised trips allow guests to bring their own food, drinks, and music aboard. The Half-Day Sail specifically notes a traditional cutter ketch as the sailing vessel and offers opportunities for guests to take the helm. Departure point for at least one listed trip is Courthouse Docks in Boston. The full-day itinerary includes landing at seldom-visited islands for wildlife viewing and beach time. Trips vary in length to suit short outings and extended island exploration. Boston Sailing Tours markets these experiences to visitors and locals seeking scenic views of Boston Harbor, historical coastal sites, and island access without a long ferry. Trip details and durations are provided so prospective customers can select the sail that best fits their timing and interests.
Book with Boston Sailing Tours