Daytrip from Boston to Martha’s Vineyard

One of the best things about being in Boston… is not being in Boston. Hey, the city is charming, bustling, and can scratch every culinary, cultural, or citified itch you have. But it’s also what’s around the greater Boston area that is such a treat. Martha’s Vineyard - only a few short, easy hours away (if you plan right) - is one of those nearby gems. So, what does a day trip look like from Beantown to the Vineyard?

Transportation

Martha’s Vineyard isn’t as small as people think. So, if you want to get a full day in, you’ll want to start early and plan your transportation as such. Coming from Boston requires a drive. If you don’t have a car (or want to splurge luxuriously on an Uber), there are buses. And many tour packages include the bus from Boston and a ferry ride. Because, yes, you’ll be taking a Cape Cod ferry to the island - itself a tranquil, sea-breeze-in-your face journey, but one that needs to be figured out. You can depart from Hyannis, Falmouth, and Woods Hole.

Exploration

So, what is Martha’s Vineyard? Or rather, what is on Martha’s Vineyard? Well, the island is made up of six towns, which are Oak Bluffs, West Tisbury, Vineyard Haven, Aquinnah, Edgartown, and Chilmark. Aquinnah is the only town that isn’t easily reachable by the Vineyard’s otherwise convenient, bus-based, public transportation system (although its stunning cliffs and Gay Head Lighthouse are a must-view). But wherever you go, shops, cottages (especially the gingerbread ones in Oak Bluffs), eats of all kinds, the sea air, beaches, everything you’ve heard about Martha’s Vineyard is there for you to take in. The most explored areas are Edgartown, Vineyard Haven, and Oak Bluffs - all connected by the No. 13 bus system. Edgartown has the most robust downtown, which takes nothing away from its charm.

Eating

Apple fritters at Back Door Donuts in Oak Bluffs. The Seafood Shanty in Edgartown, followed up by ice cream from Mad Martha’s. A slice of pizza at Chilmark General Store. Martha’s Vineyard represents the best of New England eating: running the gamut from folksy delish to high-end Michelin-level bites. You can even fish out your own clams for dinner from a pond (granted you need a license, but it’s not a painful process). The best thing to do beforehand is a bit of research into what eateries you want to indulge in. Then plan your food tour accordingly. As mentioned, Martha’s Vineyard is a collection of towns, therefore eating itineraries have to be taken into consideration. That said, Oak Bluffs seems to be the best spot for meal choices, if you had to limit yourself to one town. But really, you can’t go wrong anywhere. There’s always a munch to discover.

Beaching  

What’s visiting Martha’s Vineyard without getting the sand between your toes and posting up against the breeze off the mighty Atlantic Ocean? With well over a hundred miles of shoreline, the Vineyard has beaches for walking, beaches for relaxing, beaches for activities, and beaches that are great for all of the above.

The most popular, and therefore often the most populated, of the twenty beaches on the island is South Beach a.k.a Katama Beach. It’s named after the bay on one side, which has calmer waters than its Atlantic side. This is often the beach that people visit if they only visit one on the Vineyard, and it is truly worth the trip (despite the crowds). The supple sand cushions your feet and makes for an unsurpassed beach stroll. But if you’re feeling active, you can take a surfboard or a boogie board onto the ocean half and ride the waves. Whatever you want out of a beach, South Beach has it.

A more quaint, compact beach to visit is Menemsha Public Beach. Perfect for peaceful walks and taking in the sunset, it also has incredible seafood in the adorable nearby village of Menemsha. This is a spot to visit if you’re looking for something a little more on the quiet, contemplative side. Which, combined with a scrumptious lobster roll, makes for something close to a transcendental experience.

An even more secluded pocket of the Vineyard is East Beach, located on remote Chappaquiddick - “Chappy” to the locals. No big crowds, just tranquil swimming and uninterrupted fishing, if you so desire. Take the Chappy ferry, walk over historic Dikes Bridge, and - after you pay the entrance fee to the Trustees, who own the land - visit the nearby Japanese Gardens for added serene pleasure.

One of the more iconic Martha’s Vineyard beach experiences is out in Aquinnah: Moshup Beach. Not only is it at the foot of the famous cliffs but it’s in the same vicinity as Gay Head Lighthouse - one of the great sights on the Vineyard. Because of the cliffs, the beach itself is a bit rocky and not as plush as some other areas of the shoreline. But its also one of the more scenic experiences on an already very scenic island.

These are only a fraction of the beaches the Vineyard offers, and it’s tough to say you’ll go wrong with any sandy spot you decide to visit.  

Helpful Suggestions

Ultimately, you want to book your trip to Martha’s Vineyard from Boston as far in advance as possible. It can never hurt. Oftentimes, as you get closer, ferry spots and bus tickets get swallowed up - not to mention restaurant reservations. Whatever the case, you don’t want to be in a position of floundering around the town - unless you want to be a Vineyard bum (and there’s nothing wrong with that). Also, it behooves you to pick out specific towns or beaches to target. 

Just know, no matter how you go about your approach to Martha’s Vineyard from, say, Newbury Guest House or any other part of Boston, you’re going to be in for a treat. Whether you want to be a part of the tourist crowds in the town centers, or ramble through the rural, salt-kissed terrain of Aquinnah, you’ll have an experience you won’t soon forget.