Martha’s Vineyard. Who doesn’t want to spend a week on the island, it’s beautiful! In full disclosure we’ve never visited during the busy summer season, so I can’t speak to that. However, we have spent time on the island in the spring and fall, which are truly lovely seasons to visit. The days are still warm and the tourists have either not yet arrived before Memorial Day, or they’ve left by Labor Day.

Martha’s Vineyard
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The great thing about visiting Martha’s Vineyard is how easy it is to visit each of the villages on the island. They are, in essence, geographically compartmentalized. Take a look at this photo of a postcard on which you can see each village.

An overview of Martha’s Vineyard
Demographics

One aspect that makes the island easy to explore is the size, because it’s only 20.5 miles in length with a total area of 96 sq. miles. In other words, it’s not very big. Each village on the island offers its own charms, and with the beaches, hiking trails, golf courses and of course, the ocean, Martha’s Vineyard is truly an island paradise. Did I mention it’s also a foodie destination, especially the fresh seafood.

Although we are reasonably familiar with the island, we continue to learn each time we visit. We can find our way around the island although it can be a bit confusing at times. For example, Vineyard Haven is a community within the town of Tisbury. West Tisbury is another village and it’s where we stay. Each village, although seemingly very similar, does have distinct differences between them. With that being said, let’s take an island tour. Shall we? We’ll start at Vineyard Haven and make our way around the island.

Vineyard Haven

Vineyard Haven and Oak Bluffs are where the island ferries arrive/depart. With one exception, we’ve always arrived in Vineyard Haven. Woods Hole, Massachusetts is our departure point from the mainland. The ferry system is operated by The Steamship Authority. Reservations for passengers, bicycles, and cars can be made and paid for online. To give you an example of pricing, for the two of us and our car we pay $225.00 round trip. It’s about a 45-minute ferry ride from the mainland to the island. If it’s a clear day, it’s a beautiful ride.

One of the smaller ferries getting ready to depart Woods Hole, MA Other ferries are much larger.

If being on the water doesn’t float your boat so-to-speak, you can fly to the island.

Vineyard Haven offers visitors boutique shopping, ice creameries, bakeries and a multitude of dining options. If you like pie, don’t miss the mouth-watering Key Lime pie at Pie Chicks. It all makes for a lovely time of browsing and taking in the sites. And, there is a particular bench near the water where one (or two) can sit and take in the ocean view while enjoying one’s favorite flavor of ice cream, or a piece of pie. Just sayin.

Oak Bluffs

Oak Bluffs is right on the ocean road and as such there is usually a lovely breeze in the air. There are two big reasons why we always make a point to visit Oak Bluffs. One, we love to take a walk through the community of 318 Gingerbread Houses, which you can read our post about the houses here, and two, a must stop at Back Door Doughnuts. I mean, who doesn’t love doughnuts? We highly recommend the apple fritters.

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Edgartown

Edgartown is lovely. Well, all of Martha’s Vineyard is lovely, but Edgartown has an upscale vibe. Suffice it to say the Obamas live on Edgartown Pond. Spend an afternoon strolling along the historic streets of the town such as Water Street where one can oohhh and aahhh at the gracious homes and gardens. Enjoy a meal at one of the many eateries, do some boutique shopping, play a round of golf, or maybe go out on a yacht for the day. The Edgartown Lighthouse is one of five on the island and it’s a nice walk out to it.

Chappaquiddick

Chappaquiddick, I believe, is actually a peninsula but I’ve also read it described as a “sometime” island. I suppose it has to do with the tides. The island is reachable by two small car ferries that go back and forth. It takes 2 1/2 minutes. The peninsula/island is very small with one paved road, and just one local store, Jerry’s Place. Chappaquiddick is probably most well-known for the association with Senator Ted Kennedy who had a tragic accident in 1969 while driving across a bridge on the island.

South Beach

Just as the name says, South Beach is a long stretch of beach on the Atlantic Ocean. The area is most notably known for the wind surfing on an inland bay just across the road from the ocean beach. It’s usually quite windy.

A gray and cloudy day but the surfers loved it.
West Tisbury

West Tisbury is where we stay when we visit. We are fortunate in that we stay in the vacation home of extended family. West Tisbury is a bit rural, but since the island isn’t very big, it doesn’t take long to get anywhere on the island. If you refer to the postcard photo above, it looks as if West Tisbury is a long drive to Vineyard Haven. Actually, it’s just a quick 13-minute drive right across the island.

Martha's Vineyard
This lovely home was built by our extended family 25+ years ago. We consider ourselves very fortunate to be recipients of such generosity.

Although West Tisbury is a bit rural, there are interesting things to do. One of our favorites is a stop at Martha’s Vineyard Glassworks, which is a gallery of hand-blown glass pieces. Visitors can watch the artists work with the glass. It’s fascinating.

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See our fish?

We have a glass fish, we named Martha Tisbury, that we watched being blown from beginning to end. Truthfully, we walked away after watching the creation of our fish, but somehow Santa Claus managed to put it under our tree! Christmas magic!

If you love old-school general stores, a stop at Alley’s General Store in West Tisbury is a must. So much fun.

Our favorite beaches in West Tisbury are Lambert’s Cove and Long Point Wildlife Refuge which boasts a beautiful long stretch of white sand beach.

Chilmark

West Tisbury and Chilmark pretty much just run together, at least in my mind. It’s a lovely rural area. There is one must stop destination in Chilmark, Chilmark Pottery. The artist/owner settled on Martha’s Vineyard in the early 80’s and has been a mainstay on the island ever since. Each and every time we visit we make a stop to admire his work.

I should mention that pretty much anywhere on the island you can find a hiking trail, or a place to take a long walk. Just check an app such as AllTrails and start walking.

Aquinnah

Approximately 21 miles from Oak Bluffs you can find yourself in Aquinnah. With a population of just a few hundred, it is a rural village. Set atop the cliffs you’ll find the Aquinnah Lighthouse, one of five on the island. The views from the top are spectacular to say the least. A few shops and eateries complete a stop.

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The Aquinnah Lighthouse. Visitors can enter the lighthouse for a minimal fee.
Menemsha

Menemsha is the quintessential fishing village. It is the real deal. If you want fresh seafood just off the boat, this is the place to go. You can walk in to a number of small fish markets and place your order. We haven’t found a market with a fryer so no fries or deep fried anything, but lobster rolls, chowder, lobster bisque, etc., are on the menu. Take your order and walk down to the beach, take a seat on the retaining wall and enjoy lunch while watching the waves break. Does it get any better?

The idyllic fishing village, Menemsha
How to Spend a Week on Martha’s Vineyard

So, that’s it. We made our way around the island taking a peek at the highlights. One week is the ideal length of time to spend on Martha’s Vineyard because you can experience pretty much everything and still have down time to relax. Of course any length of time would be great; a weekend, a week, a month or an entire season.

A couple of final thoughts. The year-round population on Martha’s Vineyard is approximately 17,000 but during the summer season the number of people swells to nearly 200,000. Just like the vacation home of our extended family, more than 50% of the homes on the island are seasonal residencies. Also, it’s not an exaggeration to say that Martha’s Vineyard is expensive. If you think about it, local businesses have to rely on the tourist seasons to sustain them for the entire year. While some businesses actually close during the winter, they still have to pay rent. Dining out can be pricey as well, and keep in mind there are no fast food eateries or chain stores. Just like with any destination planning, it’s always a good idea to do your due diligence.

That being said, a week well-spent on Martha’s Vineyard makes for a wonderful vacation.

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