How to Explore Martha’s Vineyard in 48 Hours (or Less!)

Gay Head Lighthouse
Gay Head Lighthouse (Jason Paluck via Flickr)

Ah, Martha’s Vineyard. The very name conjures images of windswept beaches and Kennedy family scandals. Presidents Clinton and Obama have vacationed here. It’s an island embodied by, if you will, those pastel-colored “Black Dog Martha’s Vineyard” t-shirts you see proudly worn across the states, or those (also pastel-colored) shorts with mini crabs and martini glasses embroidered all over them.

Over the years I’ve pondered and written about this island oasis of the rich and preppy. Still, I never had a good opportunity to visit the places I’ve heard so much about, like Moshup’s Beach or the Gay Head Lighthouse and cliffs, nor have I had good reason to speak aloud charming town names like Aquinnah or Menemsha.

When the wedding of good friends in nearby Rhode Island coincided with the 4th of July weekend, Ayaz and I decided to extend our New England stay for a bit and take a quick trip from Providence to the Vineyard.

By quick, I mean, really quick: we had a whopping 24 hours to make the most of the island. Never deterred by time (or lack there-of), and always game for our next adventure, we hit the road — and it was spectacular.

Getting There

The Vineyard is only reachable by ferry, boat or small plane. Both passenger and car ferries service the island, and this is admittedly the most popular way to get here. We opted to take the ferry, but chose to leave our car behind in the ferry company’s lot — while it’s always convenient to have a car, we truly didn’t need one during our brief stay.

There are ferries from New York City and Rhode Island, but we used the Steamship Authority ferry from Falmouth in Cape Cod, MA to the town of Oak Bluffs on Martha’s Vineyard. The Falmouth terminal has paid parking lots and shuttles to the ferry for folks leaving their cars.

The $8 per person ferry ride was about 45 minutes, and completely pleasant — there were snacks, drinks and even wifi.

Where to Stay

pequot hotel martha's vineyard
Ayaz enjoying a spot o’ lemonade at the Pequot Hotel.

There are certainly nicer towns in which to stay, but if you’re only popping into the Vineyard for a night or 2 and you happen to be without a car, I’d recommend staying in Oak Bluffs. The town isn’t the most charming on the island, but it’s sure as heck convenient for a quick trip. There’s a beach, the ferry drops you off here so accommodations should be walkable, the public bus runs through here frequently, and there are plenty of shops, restaurants and activities to keep you busy.

Bed and breakfasts with wraparound porches are de rigeur here, and we stayed the night at the Pequot Hotel, which much to my delight included an afternoon snack complete with freshly-baked chocolate chip cookies and lemonade. Breakfast wasn’t shabby, either. There were quiches, cereals, baked goods, and more to choose from.

What to Do

Gay Head Lighthouse and Aquinnah Cliffs

Aquinnah Cliffs and Gay Head Lighthouse
Aquinnah Cliffs and Gay Head Lighthouse

One of the most photographed sites on the island, the lighthouse and  dramatic red and black cliffs perched upon the Vineyard’s westernmost point are truly striking. The public bus will take you directly to the site, where you’ll find a very small smattering of food stands and tchotchke shops. You can pay to climb the lighthouse and capture wraparound views of the area, or simply walk along the cliffs’ edge.

Moshup Beach

Who doesn’t love a good old-fashioned nude beach? Well, truth is, me. It’s never the people you want to see naked frolicking on the sand, is it? Anyway, I digress. A portion of Moshup is indeed clothing optional, but for the most part you’ll find regular, bathing suit-wearing folks lounging on the splendid, windswept sand and dipping toes into the chilly, crashing waves. The beach is located adjacent to the Gay Head Lighthouse and cliffs.


The fishing village of Menemsha (Jef Nickerson via Flickr)

Dun-DUN. Dun-DUN. You know what that sound is? That’s the sound of Jaws! Yes, the shark-infested horror flick was filmed in the tiny fishing village of Menemsha, which has, remarkably, remained a tiny fishing village for all these years, despite its notoriety. Stroll around the docks for a bit and be sure to stop in at one of the many fresh seafood shacks where you can belly up with a lobster roll (with meat cooked fresh from the traps) or grab some fresh steamers.

Ride the Flying Horses

If you’ve traveled to the Vineyard with the little ones, make a beeline for the Flying Horses Carousel in Oak Bluffs. Built in 1876, it’s the oldest operating carousel in the United States and is listed as an official historic landmark. Twenty hand-carved horses adorn the carousel and have manes and tails made from real horse hair. (Ew).

Watch the Sunset From Nancy’s Restaurant

nancy's restaurant
A glass of sauv blanc and a sunset.

Ask anyone for the best place to catch a sunset while enjoying a cocktail and I swear, they’ll tell you Nancy’s. Head for the upstairs restaurant or more casual lower deck and watch the sun dip low over the marina and boats. The upstairs restaurant food is quite a bit pricier than the counter service down below — but whichever you choose, you’ll be in a prime position for sunset watching.

Ride the Bus

Martha’s Vineyard has a remarkably well-organized public bus service that runs different lines accessing points throughout the entire island. Thanks to the VTA, we had absolutely no need for our car (though having one does afford more freedom to explore, obviously). With limited time on the island, we found riding the bus was a great way to see sights across the far reaches of the Vineyard. Of course, you can also line up a proper bus tour from one of the outfitters in town, and get guided commentary during your trip, but we went for the cost-effective VTA day pass — a whopping $7 — whee!