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.
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.
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.