When I planned our Martha’s Vineyard day trip, I didn’t know much about the island, other than that it was a favorite summer escape for American royalty. It’s one of those places where history and headlines quietly overlap. From presidential summers to the final flight of John F. Kennedy Jr., the island carries stories that go far beyond what you see on the surface. As a matter of fact, it was only 2 days after our visit that Obama’s chef mysteriously drowned there.
So for me, this Martha’s Vineyard day trip was part historical curiosity, part current-event fascination, and part mystery.
What I found instead was the real reason this island holds so much appeal.
Although I didn’t know it at the time, the Martha’s Vineyard day trip would end up being my favorite of the entire summer road trip.
How to Get to Martha’s Vineyard (and What We Did Instead)
We drove our rental car to the ferry, but we did not take it across to the island. Turns out, you need to be organized enough to reserve a vehicle spot in advance, so we went as walk-ons instead.
My husband, a true sports car lover, had already found a rental place within walking distance of the ferry terminal. He booked us a convertible because really, what better way is there to explore an island in the summer?
We boarded the ferry at Woods Hole around noon, and by 1 p.m. we were stepping onto Martha’s Vineyard.
How to Get Around Martha’s Vineyard (Without a Car Ferry Reservation)
I expected mansions upon mansions—the kind of place you might have once seen on Lifestyles of the Rich and Famous. I doubted we would even get close to the water.
I could not have been more wrong.
Oak Bluffs greeted us with color, movement, and that breezy waterfront energy that instantly makes you want to linger.
Ocean Park sits at the center, overlooking the bluffs the area is named for. A traditional white gazebo anchors the park, surrounded on the other three sides by streets lined with Victorian homes.
After picking up a map at the ferry terminal, we walked a block or two to grab our rental car—and just like that, we had the freedom to explore the island at our own pace.
Oak Bluffs: History, Gingerbread Cottages, and the Oldest Carousel
Oak Bluffs has a much more interesting history than what might have been portrayed on Robin Leach’s famous ’80s show.
I was thinking wealth, wineries, and grapes, right?
Instead, Oak Bluffs began as a religious campground. People came for summer revivals and stayed in tents. Over time, those tents evolved into the colorful gingerbread cottages you see today.
In the late 1800s and early 1900s, it was also one of the few places that welcomed Black families on vacation. Over the years, notable figures like Spike Lee, Oprah, and the Obamas have all had ties to the area.
While in Oak Bluffs, don’t miss the carousel. Built in 1876, it is considered the oldest operating platform carousel in the United States.
Aquinnah Cliffs Overlook: One of the Best Views during your Martha’s Vineyard Day Trip
Once we got settled in, lowered the roof, and pointed ourselves across the island, our first stop was the Aquinnah Cliffs Overlook—home to the dramatic clay cliffs and the historic Gay Head Lighthouse.
We drove across the island through rural areas that looked like a mix of hobby farms and part-time cottages, surrounded by flowers and lush shades of green. As we approached the western end of the island, the landscape began to rise.
We were fortunate to find parking quickly and made our way uphill past a small row of weathered cedar-shake buildings. Shops, food stands, and information stations lined the path leading to the viewpoints.
Yes, the view was stunning. It had the kind of dramatic coastal beauty I usually associate with photos of the Scottish Highlands or the cliffs of Dover—except this was right here in the USA.
Gay Head Lighthouse: A Piece of Martha’s Vineyard History
Further along stood a small but striking lighthouse made of solid brown brick.
Built in 1799, the Gay Head Lighthouse sits so close to the cliffs that it had to be moved back 130 feet in 2015 to keep it from falling into the sea.
It was the first lighthouse built on Martha’s Vineyard and helped guide ships through the tricky waters near the cliffs and the Elizabeth Islands. It also has a connection to the Aquinnah Wampanoag community, including a history of Native American lighthouse keepers.
We climbed to the top, and for me, the circular catwalk was the highlight. Not only could we take in the view, but we could feel the wind rushing off the water and past us.
Standing there overlooking Aquinnah, it’s easy to think the cliffs have always looked this way—but they’re constantly shifting, as the lighthouse itself proves.
Menemsha Fish Market: The Best Lobster Roll on Martha’s Vineyard?
We eventually made our way back to the car, and with the roof down, we drove until something caught our eye.
That next stop was Menemsha Fish Market.
We had pulled over because we spotted a beach—but what we found was so much better.
A small fishing village and harbor sit just behind the shoreline. While my husband let his son enjoy the front seat of the convertible during a joy ride, I wandered along the beach and into the fishing area.
Much to my surprise, I found fresh lobster—a lobster roll without the roll.
I didn’t try every lobster on the island, but I was convinced this had to be the best lobster roll on Martha’s Vineyard!
Before leaving that side of the island, we stopped briefly at Eastville Point Beach. It wasn’t a long stop, but it was one of those quiet little moments that stays with you. Two sailboats moved in tandem across the horizon while a few more waited nearby, their masts and hulls creating that peaceful harbor scene Martha’s Vineyard seemed to do so effortlessly.
Telegraph Hill & Vineyard Haven: A Quiet Stop and an Unexpected Crowd
As we continued driving, we spotted what looked like a lighthouse tucked into a quiet neighborhood.
We almost missed it behind the trees but stopped when we noticed a small sign marking the area as Telegraph Hill—a reminder that long before cell service and GPS, this elevated point was used to spot ships and send signals inland.
The East Chop lighthouse was closed, but the setting felt quiet and slightly removed—like a place that had been watching the island change for a very long time.
We later made our way into Vineyard Haven, hoping to explore and shop, but quickly realized we had arrived during the Tisbury Street Fair. The streets were packed, parking was impossible, and the energy was high.
It became one of those “we’ll come back next time” stops.
Is Martha’s Vineyard Worth Visiting?
With the last ferry of the day approaching, we made our way back to Oak Bluffs.
My stepson did a little shopping while James and I found a spot overlooking the harbor and ordered drinks, letting the day settle in.
I came expecting something polished—maybe even a little out of reach.
What I found instead was an island that was naturally dramatic.
A place that shifts quickly—from soaring cliffs to working fishing docks to quiet neighborhoods and busy harbor towns—all in a single afternoon.
It wasn’t one moment that made Martha’s Vineyard day trip stand out.
It was how quickly it kept changing on us.
And somewhere between the cliffs, the lobster, and that final drink overlooking the harbor… it became my favorite day of the entire trip.
Martha’s Vineyard Day Trip Map Route
What’s Next on the Road Trip
Next up, we head into Boston for two consecutive days—where the pace picks up and history feels a little less quiet.
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