Full Day Sailing & Island Charters by Boston Sailing Tours
Difficulty
easy
Duration
6 hours
Fitness Level
Suitable for all fitness levels; requires basic mobility for boarding and walking uneven island terrain.
Overview
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.
Full Day Sailing & Island Experience
For all ages! • 6 Hours • Up to 6 People
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About This Adventure
Embark on a unique 6-hour sailing adventure from Boston, exploring the secluded Grape, Lovells, and Bumpkin Islands. Disembark to discover stunning wildlife, pristine beaches, and historical military remnants. Enjoy the freedom to bring your own food and drinks while experiencing the tranquility of these rarely visited islands.
20% is due at the time of booking. The remaining balance is due at the time of the charter.
Departing Location
Boston Sailing Tours departure location is at Courthouse Docks, Located Across From Marcelino's Seaport - 2 Northern Ave, Boston, MA 02210. All trips will depart from this location. Paid public parking is available. MAP
Duration
6 Hours
About
A Unique Experience: We are the unique sailing charter company in Boston that offers an exploration tour of Grape, Lovells, and Bumpkin Islands, only accessible by private boat. You can disembark and discover the islands while the boat and captain wait for you.
What is there? An amazing diversity of wildlife can be observed. You will be able to experience secluded beaches with spectacular views of the other islands and the ocean. You will also find remains of a military installation dating from the Revolutionary War to World War II and old trails to hike around. The islands receive very few visitors every year. During your tour, you are likely to be the only one.
What to Bring
CONSIDER TO BRING Sailors should dress for safety, comfort, and weather. In spring and fall, dress in layers and bring a jacket or sweatshirt; it can be cooler at sea than on land.
In summer, bring a hat, sunglasses, and sunscreen.
For safety and comfort, soft-soled shoes like boat shoes or sneakers are the preferred footwear aboard the Francesca. You will be asked to go barefoot for safety reasons if you wear hard-soled shoes or high heels on board.
WHAT NOT TO BRING You’re also welcome to bring aboard your own food and drinks. We recommend keeping food to snacks and easy-to-eat items like sandwiches. Plan as if you are going on a picnic as we do not have a formal table on board. Drinks can include alcoholic and non-alcoholic beverages.
Per Federal regulation no marijuana or marijuana-containing products no illicit drugs
Food, Drinks, Music
• You’re welcome to bring your favorite food, drinks, and music. • We recommend easy-to-eat items and canned drinks. • We do not have a formal table in the cockpit • We have complimentary water and sodas on board
FULL GUEST INFORMATION
Adventure Tips
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.
Local Insights
Wildlife
- Ospreys nesting on island cliffs
- Harbor seals often spotted near shoreline rocks
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.
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Adventure Hotspots in Boston, MA
Frequently Asked Questions
Recommended Gear
Layered Clothing
Allows adjustment to changing temperatures and ocean breezes during the trip.
spring specific
Sunscreen
Protects exposed skin from strong sun while sailing and on the islands.
summer specific
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 specific