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

4.93

(123 reviews)

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.