Martha’s Vineyard: 3hr Island Tour with Local Stops & Cliffs

Summary

Oak bluffs to aquinnah cliffs in three hours of island color and local tales

You’ll ride through Martha’s Vineyard with a local guide who knows every shortcut and story, stopping at rainbow-bright gingerbread houses, historic Edgartown streets, and finally the windswept Aquinnah Cliffs. Expect salty air, quick laughs with fellow travelers, small surprises along the way — plus time to stand quietly where land meets ocean.

What’s the experience like?

I still remember how the ferry smell clung to my jacket when we hopped off at Oak Bluffs — all salt and engine. The van was waiting just where they’d said, diagonally across from the ticket office, and our driver (Ben — he grew up here but left for college and came back, which he told us before we’d even buckled up) waved us over. It felt like joining someone’s family road trip more than a regular Martha’s Vineyard tour. We squeezed into the seats, windows already fogging a bit from the morning chill. Ben grinned and said “Don’t worry, AC works too well sometimes.”

First stop: those gingerbread houses. Painted every color you can think of — honestly, I’m not sure how the pinks don’t clash with the blues but somehow it works. Ben told us about camp meetings and how kids weren’t allowed at first (which made me laugh because now it looks like a place built for kids). He pointed out his favorite porch swing and then let us wander for ten minutes. I caught this whiff of cinnamon from someone’s open kitchen window; it almost made me want to knock and ask what they were baking. We passed Vineyard Haven and Edgartown, hearing about whaling days and lighthouses — quick flashes of history between stretches of quiet road.

The highlight was definitely Aquinnah Cliffs. We had about fifteen minutes there — not enough if you want to hike around but just right for standing at the edge, wind in your face, watching gulls float above those wild stripes of clay. The colors shift with the sun; I didn’t expect that part. A local woman was selling jewelry by her car and told me she’d been making shell necklaces since she was a kid. I bought one for my niece (she’ll probably lose it in a week but whatever). On the way back through Chilmark and Menemsha, Ben slowed down so we could see people jumping off that bridge from Jaws — some guy did a cannonball and everyone on our bus cheered.

Three hours went fast. There’s something about seeing all six towns in one go that makes you realize how different each corner feels — like little worlds stitched together by these winding roads and old stories. I keep thinking about those cliffs though; maybe next time I’ll stay longer just to watch the light change.

Step-by-step itinerary

Day 1 — 3-hour Martha's Vineyard island tour

• Visit oldest operating carousel
• Pass by historic Edgartown whaling site
• Stop at Aquinnah Cliffs
• Pass by 1828 Lighthouse Keeper's home
• See Gingerbread Houses area
• View Jaws movie bridge jump site
• Visit operating Martha's Vineyard Lighthouse

Top questions

How long is the Martha’s Vineyard island tour?

The tour lasts 3 hours total, including stops.

Where does the tour start on Martha’s Vineyard?

Tours depart diagonally across from the Oak Bluffs Steamship Authority Ticket Office near the Soldier Statue.

Is pickup included for this day trip?

The tour starts at a central location in Oak Bluffs; hotel pickup is not included.

Are children allowed on this Martha’s Vineyard tour?

Children must be at least 10 years old to join this tour.

What are some highlights included on this island tour?

You’ll see Oak Bluffs’ gingerbread houses, Edgartown’s historic spots, Aquinnah Cliffs, Menemsha bridge (from Jaws), lighthouses, and more.

Is lunch included during the 3-hour tour?

No meals are included; there is time for snacks during stops if you bring your own.

What kind of vehicle is used for this shared island tour?

The tour uses comfortable air-conditioned vans or mini-buses marked "MV Transport."

Does this Martha’s Vineyard day trip operate in bad weather?

Yes, tours run in all weather conditions; dress appropriately.

What’s included

Your day includes transportation in an air-conditioned van or mini-bus starting from Oak Bluffs with live commentary by a professional local driver-guide. You’ll visit all six towns on Martha’s Vineyard with narrated stops including fifteen minutes at Aquinnah Cliffs. The small-group setting makes it easy to ask questions or just enjoy the views as you go.