BOSTON BOAT TOUR FIELD GUIDE
Solitude and Shorelines: A Six‑Hour Sail to Boston’s Hidden Islands
A private, six-hour charter from Boston that lands you on rarely visited Grape, Lovells and Bumpkin Islands—this guide explains what to expect, what to bring, and how the day unfolds.
Solitude and Shorelines: A Six‑Hour Sail to Boston’s Hidden Islands.
Adventure brief
Solitude and Shorelines: A Six‑Hour Sail to Boston’s Hidden Islands
Embark on a unique 6‑hour sailing adventure from Boston to the secluded Grape, Lovells and Bumpkin Islands. The charter lets you disembark to explore wildlife, quiet beaches and historical military remnants while the captain and vessel remain on station, offering a rare chance to experience islands that receive very few visitors each year.
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.
Route Schematic
Itinerary Route Schematic
Stops focus on three small islands in Boston Harbor where you disembark to explore beaches, trails and historical remnants.
Grape Island
A first landing to explore shorelines, observe wildlife and walk short trails.
Lovells Island
Time to explore beaches and remnants of coastal military installations while enjoying expansive harbor views.
Bumpkin Island
A final island visit with additional shore time for short hikes and beachside relaxation before returning to Boston.
Passengers should be prepared for short shore landings and walking on island trails; the operator runs private charters and the vessel remains available while you explore.
Highlights
Outing Highlights
Three private islands within a day’s sail
This full‑day charter visits Grape, Lovells and Bumpkin Islands—each accessible only by private boat—allowing time to step ashore, hike old trails and take in views across the harbor.
Secluded beaches and abundant wildlife
Expect an amazing diversity of wildlife and the sense of near‑solitude that comes from islands that see very few visitors annually—ideal for quiet observation and photography.
Fingerprints of coastal defense
Onshore you’ll find remains of military installations spanning the Revolutionary era through World War II, scattered among beaches and trails that invite exploration.
What the day feels like
What the day feels like
The day is a measured balance of sailing and shore time: a private vessel leaves Boston’s waterfront and cruises out to a string of islands where you can step ashore to hike, picnic and inspect coastal ruins while the captain waits offshore. The itinerary is built for a relaxed pace over the course of a six‑hour charter.
Suitability
Who it's for
Who this trip suits
Practical planner
Details to review before reserving
The tour is a 6‑hour private charter.
Dress in layers; in spring and fall bring a jacket or sweatshirt. In summer bring a hat, sunglasses and sunscreen. Wear soft‑soled shoes (boat shoes or sneakers); hard‑soled shoes or high heels may be disallowed and you may be asked to go barefoot for safety. Bring easy‑to‑eat picnic foods; alcoholic and non‑alcoholic drinks are permitted.
Departure is from Boston Sailing Tours at Courthouse Docks, across from Marcelino's Seaport at 2 Northern Ave, Boston, MA 02210; paid public parking is available.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the sailing and island experience?
The charter is six hours in duration.
Where does the trip depart from and is there parking?
Trips depart from Courthouse Docks (2 Northern Ave, Boston, MA 02210) and paid public parking is available.
Can I bring my own food and drinks?
Yes—you’re welcome to bring your own food and drinks; light picnic‑style items and canned drinks are recommended. Complimentary water and sodas are provided on board.
How many people can join a charter?
Charters accommodate up to six people.
What are the payment terms?
Twenty percent is due at the time of booking; the remaining balance is due at the time of the charter.
Are there restrictions on items to bring?
Per federal regulation, marijuana or marijuana‑containing products and illicit drugs are not permitted aboard.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-08-18T01:18:37.030Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.