Martha’s Vineyard: Full Island Tour with Menemsha & Aquinnah Cliffs

Summary

Six towns, clay cliffs, gingerbread houses and salty air on Martha’s Vineyard

You’ll ride in an air-conditioned van around Martha’s Vineyard with a local guide, stopping at all six towns—from colorful Aquinnah Cliffs to Menemsha’s seaport and Oak Bluffs’ gingerbread cottages. Hear stories about whaling captains and movie scenes as you wander beaches and lighthouses. It’s three hours that somehow feel both full and easygoing—you might even forget your phone for a while.

What’s the experience like?

I didn’t expect the colors at Aquinnah to look so unreal in person — like someone had taken a paintbrush to the cliffs. We’d just hopped out of the van, still a bit chilly from the AC (which honestly felt good after the sun), and our guide, Mike, started telling us about the Wampanoag people who’ve lived here forever. The wind smelled faintly of salt and something earthy I couldn’t place. I tried to take a photo but it never really catches it right, you know?

We covered all six towns in three hours, which sounds rushed but didn’t feel that way. There was this stop in Menemsha where we watched a couple of kids daring each other to jump off the Jaws bridge — apparently people do that all day. The water looked freezing but they were laughing so hard I almost wanted to try it myself (I didn’t). Mike pointed out some old whaling captain’s houses as we passed through Edgartown; their porches looked like they’d seen every kind of weather.

The gingerbread houses in Oak Bluffs were smaller than I pictured — almost like storybook cottages, except with real people watering plants out front. I tried to pronounce “Aquinnah” right and Li laughed when I butchered it (she grew up here; she said everyone gets it wrong). The whole island feels both familiar and strange at once. By the time we circled back to the van for one last look at the lighthouse above the cliffs, I realized I hadn’t checked my phone once during the tour. That doesn’t happen much these days.

Step-by-step itinerary

Day 1 — Full island tour with key stops

• Pass by Jaws filming beach
• Visit Aquinnah Cliffs
• Pass by Aquinnah lighthouse
• Pass by Gingerbread Houses
• Pass by oldest merry-go-round
• Stop at best beach for sunsets
• Pass by whaling captains church
• Pass by Edgartown lighthouse

Top questions

How long does the Martha’s Vineyard full island tour last?

The tour lasts approximately three hours from start to finish.

Does this tour include stops at Aquinnah Cliffs?

Yes, there is a stop at Aquinnah Cliffs where you can get out and explore.

Are gingerbread houses included in the itinerary?

Yes, you’ll visit Oak Bluffs to see the famous gingerbread houses.

Is transportation air-conditioned?

Yes, travel is in comfortable air-conditioned Ford Transit vans.

Can infants or small children join this tour?

Yes, infants and small children can ride in a pram or stroller on this tour.

Are service animals allowed on this Martha’s Vineyard tour?

Yes, service animals are permitted during the tour.

Will there be opportunities for food or snacks?

You’ll have a chance for quick chowder or lobster bisque at Menemsha Beach.

Is public transportation nearby for meeting up?

Yes, there are public transportation options available close by.

What’s included

Your day includes pickup in an air-conditioned high-top van with large windows for sightseeing comfort as you travel between all six towns of Martha’s Vineyard. A local guide shares stories along the way while you stop at places like Aquinnah Cliffs and Menemsha seaport—with time to step out for photos or even grab some chowder if you want before heading back.