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.
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Difficulty
easy
Duration
6 hours
Fitness Level
Suitable for all fitness levels; requires basic mobility for boarding and walking uneven island terrain.
Wildlife
History
The islands served as key defensive points from the Revolutionary War through World War II, with visible remains of old fortifications and gun emplacements.
Conservation
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
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.
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.
Tours Offered
3
Two-hour, half-day, full-day options
Vessel Type
Cutter ketch
Traditional cutter ketch available
Trip Durations
2–6 hours
Short to full-day sails
Islands Visited
Grape · Lovells · Bumpkin
Onshore stops and wildlife viewing
Reserve a 2-hour, half-day, or full-day trip from Courthouse Docks — limited seats per sail, book early.
Wear soft-soled shoes
Hard-soled shoes and heels aren’t allowed on board for safety; opt for sneakers or boat shoes.
Bring your own picnic
You’re welcome to bring snacks, sandwiches, and drinks to enjoy on board or ashore.
Dress in layers
Ocean breezes can be cool even in summer, so prepare with layered clothing and a windbreaker.
Respect island wildlife
Stay on marked trails and avoid disturbing nesting birds and other animals during your visit.
Layered Clothing
Allows adjustment to changing temperatures and ocean breezes during the trip.
spring
Sunscreen
Protects exposed skin from strong sun while sailing and on the islands.
summer
Soft-soled Shoes
Provides safety on deck and comfort for island hikes.
Hat & Sunglasses
Protects eyes and face from sun glare reflecting off the water.
summer