Island-Hopping Boston Harbor: A Private Sail to Grape, Lovells, and Bumpkin
A private, six-hour sail to quiet beaches and historic islands—no ferry crowds, just wind, tide, and time.
The mainsail snaps awake and the harbor answers. Boston’s skyline leans back as the bow noses into open water, gulls riding the breeze like they own it—because they do. From the Courthouse Docks in the Seaport, the city feels close enough to touch, yet a few tacks later the edges soften. Water takes the lead, the wind urges you on, and the islands—low green humps shaped by glaciers—begin to rise out of the chop like quiet invitations.
Trail Wisdom
Dress for the Harbor, Not the City
It’s often 5–10°F cooler on the water; pack a windproof layer even on sunny days.
Footwear That Works On Deck and Shore
Wear soft-soled shoes for the boat and bring sandals or light hikers for cobble and sand landings.
Plan a Smart Picnic
Pack easy, handheld foods and canned drinks—there’s no formal table aboard and trash must be packed out.
Mind the Sun and Bugs
Polarized sunglasses and sunscreen are key; carry bug spray for marshy spots, especially mid-summer.
Local Knowledge
Hidden Gems
- •Lovells Island’s oceanside bunkers with sweeping Atlantic views
- •Bumpkin Island foundations and quiet western beaches at low tide
Wildlife
Osprey, Snowy egrets
Conservation Note
These islands are part of Boston Harbor Islands National and State Park—stay on trails, pack out trash, and give nesting shorebirds wide berth.
Grape Island saw a 1775 skirmish known as the Grape Island Alarm; Lovells and nearby islands hosted military installations through World War II.
Seasonal Guide
spring
Best for: Cool, steady winds, Quiet island trails
Challenges: Chilly sea breeze, Occasional fog
Crisp sailing with fewer boats on the water. Layers and a shell make shore exploration comfortable.
summer
Best for: Warm swims, Long beach picnics
Challenges: Strong sun exposure, Greenhead flies in July–August
Peak season for island time and wildlife activity. Sun protection and bug spray keep the day dialed.
fall
Best for: Clear skies and stable winds, Fewer crowds
Challenges: Cooler afternoons, Shorter daylight
Golden light and great sailing conditions. Pack a warm layer for the ride back to the Seaport.
winter
Best for: Brisk harbor views, Potential seal sightings
Challenges: Cold temps, Limited charter availability
Cold air, quiet waters, and limited operations. If available, bundle up and keep trips short and focused.
Photographer's Notes
What to Bring
Lightweight Windproof JacketEssential
Harbor winds can chill even sunny days; a shell keeps you comfortable under sail and on beaches.
Polarized SunglassesEssential
Cuts glare on the water and helps spot wildlife and underwater features near shore.
Compact Dry Bag
Keeps phone, camera, and snacks dry during spray or damp landings.
Bug Spray (EPA-registered)
Helps deter greenheads and mosquitoes around marshy island sections.
Common Questions
Can I bring my own food and drinks?
Yes—picnic-style food and canned drinks are encouraged. Complimentary water and sodas are provided, and all trash must be packed out.
Do we get off the boat to explore the islands?
Yes. You can disembark on Grape, Lovells, and Bumpkin to walk trails and beaches while the captain waits offshore.
Is prior sailing experience required?
No. The trip is captained, and guests are not required to have sailing experience.
What should I wear on my feet?
Soft-soled shoes on the boat (no hard soles or heels). Bring sandals or light hikers for sandy and cobble shorelines.
Are restrooms available on the islands?
Facilities are limited or seasonal. Plan accordingly and use onboard facilities when available.
Is the trip suitable for kids?
Yes. This private charter is family-friendly; bring sun protection, snacks, and layers to keep kids comfortable.
What to Pack
Wind shell, polarized sunglasses, picnic-style lunch with plenty of water, and a compact dry bag—each keeps you comfortable, protected, and organized on deck and ashore.
Did You Know
In May 1775, colonists clashed with British troops on Grape Island over hay for livestock—the “Grape Island Alarm,” one of the Revolution’s earliest harbor skirmishes.
Quick Travel Tips
Arrive 15–20 minutes early to find the Courthouse Docks; rideshare is easiest in the Seaport. Pack sun protection even on overcast days—UV bounces off water. Bring bug spray in midsummer for marshy island sections. Expect good cell service near Boston, but it can be spotty on the outer islands.
Local Flavor
Post-sail, grab lobster rolls at The Barking Crab, oysters at Row 34, or a hazy IPA at Trillium Fort Point. If you’ve got time before or after, the ICA Boston sits on the waterfront with rotating exhibits and a harbor-facing deck that stretches the day out a little longer.
Logistics Snapshot
Closest airport: Boston Logan (BOS). Departure: Courthouse Docks, Seaport (2 Northern Ave). 5–10 minutes by car from Downtown/Back Bay. Cell service is generally strong near the city; can fade on the outer islands. No permits needed for this private charter; BYO food and drinks are allowed (no marijuana per federal law).
Sustainability Note
Boston Harbor recovered thanks to decades of cleanup—keep it that way. Pack out all trash, avoid fragile dune vegetation, and maintain distance from nesting birds and eelgrass beds.
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