Martha’s Vineyard: Private Island Tour with Cliffs, Lighthouses & Pickup

★★★★★★★★★★ 4.91 (88 reviews) 98% rated it 5 stars

Free cancellationExcellent quality

1/31

Duration3h

GroupPrivate

LanguagesEN

PickupAt your hotel

Private drive past lighthouses, cliffs & colorful cottages in Martha’s Vineyard

You’ll ride in comfort past Martha’s Vineyard’s lighthouses and historic homes, walk along Aquinnah Cliffs with their wild colors, taste fresh local seafood from Wampanoag vendors, and wander through Oak Bluffs’ famous gingerbread cottages—all with stories from a local guide. It’s relaxed but full of little moments you’ll remember long after you leave.

Step-by-step itinerary

Private guided tour of Martha's Vineyard

Drive past Steamship Authority Wharf
Drive along Vineyard Haven's Historic Main Street
Stop at West Chop lighthouse and bluff
Drive past West Chop Club and Elizabeth Islands overlook
Stop for photos at Elizabeth Islands overlook
Walk around Aquinnah Cliffs and take pictures
Learn about Aquinnah Lighthouse relocation
Drive along Main Street in Edgartown
Stop at Edgartown lighthouse and Harbor View Hotel
Drive past Jaws Bridge and Sengekontacket Pond
Stop for pictures at Gingerbread Cottages
Drive along Oak Bluffs harbor and East Chop bluff
Return to Vineyard Haven and drop off at terminal

The Experience

We rolled off the ferry at Vineyard Haven and our guide—Tom, who grew up on the island—was already waving from his spotless mini-van. He handed us cold water (needed it; I always forget how salty the air is here) and we set off down Main Street. The houses looked almost too perfect, but Tom pointed out which ones were old whaling captain homes and which were just pretending. He knew every shortcut. We drifted by West Chop Lighthouse, where the wind picked up and you could smell pine mixed with ocean. I tried to take a photo through the window but mostly got my own reflection.

The best part for me was Aquinnah Cliffs. We stepped out and the wind nearly stole my hat. The clay cliffs looked painted, honestly—I’d seen photos but standing there was different. There were two Wampanoag women selling seafood and I got a fried scallop roll that dripped butter down my wrist (worth it). Tom told us about how they moved the lighthouse to save it from falling into the sea—imagine moving a whole lighthouse! We wandered around for a bit, everyone sort of quiet just looking out at Nomans’ Land and those distant islands.

Later we wound through Edgartown—old churches, white fences, people waving from porches like they actually knew us. At Jaws Bridge I half-expected someone to jump in (no takers today). Oak Bluffs had these wild gingerbread cottages all painted up like candy; I kept losing track of which one I’d already photographed. By then I’d stopped trying to keep track of time or directions—Tom had it handled. He dropped us back at the Steamship Authority Terminal with just enough time to grab ice cream before our boat left. Still thinking about that view from Aquinnah though… kind of sticks with you.

What’s included

Your day includes pickup at the Steamship Authority Wharf in Vineyard Haven, bottled water for everyone (trust me—you’ll want it), a super clean luxury mini-van just for your group (up to five people), all historical commentary as you pass through six island towns with your professional driver-guide sharing stories both old and new along every stop.

Good to know

Easy physical levelPublic transport nearbyInfants must sit on laps

Operated by Laid Back Tours