Martha’s Vineyard Private Tour: 6 Towns, Carousel & Cliffs

Summary

Private drive through Martha’s Vineyard towns old whaling stories gingerbread houses and clay cliffs

You’ll ride through six very different towns on Martha’s Vineyard with a local guide—see Victorian cottages in Oak Bluffs, taste fresh chowder by Menemsha harbor, walk beneath white columns in Edgartown, and stand above the painted clay cliffs of Aquinnah with Atlantic winds in your hair. It feels like you’re borrowing someone else’s island life for a day.

What’s the experience like?

I didn’t expect the air in Oak Bluffs to smell so much like salt and grass — kind of sweet, actually. Our guide, Tom (he grew up here), started us at the Flying Horses Carousel. It’s apparently the oldest in America, but what I remember most is the faded paint and how everyone—kids and adults—seemed to laugh the same way when they caught the brass ring. I tried it once and missed, which Tom said was “pretty standard for first-timers.” No judgment.

We wandered through those wild gingerbread cottages next. They’re all colors you’d never put together on purpose—lavender next to lime green—and you can still see old names painted above some doors. Tom told us about summer revivals and how people would sing under the open-air tabernacle. I could hear someone practicing piano inside one cottage as we walked by. It felt like a place that doesn’t care about time much.

Edgartown was different—white houses, crisp fences, everything a bit more serious. We stopped at the Old Whaling Church (the columns are huge) and then strolled down to see the Edgartown Harbor Lighthouse poking out over gray water. The wind picked up there; I had to pull my jacket closer. Later, we passed through Vineyard Haven, which Tom called “the front door” of Martha’s Vineyard. He waved at a guy unloading fish from a truck—everyone seems to know each other here.

Up-island felt quieter—rolling hills, stone walls tangled with vines, sheep grazing like they owned the place. We made a quick stop in Menemsha for clam chowder (still thinking about that peppery broth), then headed for Aquinnah Cliffs. The colors in those cliffs don’t look real—reds and purples streaked through yellow clay—and there’s this lighthouse just sitting on top like it’s keeping watch over everything. The Atlantic wind is strong up there; it smells sharp and cold. We stretched our legs and took photos but mostly just stood around looking out at all that water. On the way back we crossed that bridge from Jaws—the movie one—which made everyone laugh for some reason.

Step-by-step itinerary

Day 1 — Explore Martha's Vineyard highlights

• Visit oldest platform carousel
• See Clay Cliffs of Aquinnah
• View Gingerbread Cottages and East Chop Lighthouse
• Tour New England Whaling Town

Top questions

How long does this Martha's Vineyard private tour take?

The tour covers all six towns with stops and typically lasts around half a day, depending on your pace and interests.

Is hotel or ferry pickup included?

Yes, pickup is included—you can arrange for pickup from your hotel or nearby ferry terminal with your guide.

Can infants or small children join this private tour?

Yes, infants and small children are welcome; specialized infant seats are available if needed.

What are some highlights of this private Martha's Vineyard tour?

You’ll visit Oak Bluffs’ carousel and gingerbread cottages, Edgartown’s lighthouse and whaling church, Menemsha fishing village, Aquinnah Cliffs, plus scenic countryside stops.

Is this tour suitable for people with limited mobility?

The tour is suitable for all physical fitness levels; prams or strollers can be accommodated easily.

Can we customize our route or stops during the day?

Yes—the itinerary is flexible and can be tailored to your group’s interests or needs along the way.

What’s included

Your day includes pickup (hotel or ferry), a comfortable air-conditioned vehicle just for your group of up to six people, an easygoing local guide who knows every shortcut (and story), plus plenty of chances to get out for photos or snacks along the way—even specialized infant seats if you need them.