5 Days in Martha’s Vineyard

Martha’s Vineyard. It’s the picturesque island right out of a fairytale. The colorful gingerbread cottages, clean beaches, old light houses, and a working fishing village earns Martha’s Vineyard a spot on your destination bucket list. It’s one of the biggest summer destinations in America, not just for average people like you and me but for celebrities as well. If that doesn’t prove it’s worth visiting at least once, nothing does. In full disclosure, I will admit, it is quite expensive but depending on your budget, it’s so worth it.

Martha’s Vineyard is an island off of Cape Cod in Massachusetts. With it being New England’s largest island, it is easy to get overwhelmed with itinerary ideas. But no worries, we’ve got you covered!

Day 1:

First things first, learn the way around the island. Martha’s Vineyard is made up of 6 towns so there is quite a wide area to discover.

As always, the hotel is a great starting point! It really doesn’t matter where you stay but the Winnetu Oceanside Resort in Edgartown is our recommendation.


The Winnetu, while not exactly on the beach, has wonderful views of the ocean. The rooms start at just under $500 a night but it is soo worth it.

The rest of the day is perfect for driving from town to town just to learn your way around and to find the best routes.


Day 2:

This is the day I would spend in Edgartown (mostly because that is where the hotel is, if you stay at the Winnetu).

If you are a fan of the Steven Spielberg movie Jaws, you are probably aware that the movie was filmed in Martha’s Vineyard back in 1975 and the famous bridge, known today as the “Jaws Bridge” is still there and is now an iconic landmark for tourists.

Jaws Bridge

Though the signs tell you not to, jumping off of the bridge has become a staple for tourists and it is considered a summer right of passage for some. If you have no interest in actually jumping off of the bridge, you will definitely have a few laughs while watching other people do it!

If you are into lighthouses, stop by the Edgartown Lighthouse while you are in the area.

Edgartown Lighthouse


Finally, I would end the day with dinner at the Wharf.

The Wharf Burger

Being a part of New England, there is no doubt they have great seafood but I’d go for the burgers. Their burgers took us back there three different times during our trip.


Day 3:

Oak Bluffs is next to Edgartown and is filled with a variety of activities.

It too has a lighthouse! The East Chop Lighthouse.


Another great experience in Oak Bluffs is taking an oyster farm tour with Cottage City Oysters. Oyster Farms are not your typical farm and it’s interesting to see the process the oysters we eat go through to get to our table.


The number one thing you must do in Oak Bluffs is check out the gingerbread cottages. They are a Martha’s Vineyard staple and no trip to the island is complete without walking through this little cottage city.


After walking around the cottages, be sure to stop at Ben and Bill’s for some one of a kind lobster ice cream. Yes, you read that right. Lobster ice cream, with real chunks of lobster and butter.

lobster ice cream

It’s not exactly the best flavor, but it’s the experience that counts. Right?


Day 4:

The towns of Chilmark and Aquinnah are a great place to spend the last full day in the Vineyard. Both located at the westernmost part of the island. Start the day off in Aquinnah visiting the Aquinnah Cliffs. The cliffs are a National Historic Landmark owned by the Wampanoag Tribe of Gay Head so you can’t actually go up on the cliffs but the views are still amazing. They were formed by glaciers millions of years ago and if you go at the right time of day, the array of colors are absolutely stunning.

Aquinnah Cliffs

And while you’re at it, check out the Gay Head Lighthouse!

If you want to spend some time on the beach, Aquinnah has one of the most picture perfect beaches on Martha’s Vineyard!

And finally, a great way to end the day is at Menemsha, a fishing village in the town of Chilmark. Stop by Larsen’s Fish Market for some fresh seafood to enjoy while watching the sun set over the harbor.

Larsen's Fish Market


Day 5:

Wake up and head to Vineyard Haven for some fresh baked muffins at the famous Black Dog Bakery Cafe. If you are not up in time for breakfast, don’t worry. They serve lunch as well!

And finally, the perfect way bring the trip to an end is to stop by Island Alpaca on your way to catch the Ferry to spend time with some of the cutest and huggable alpaca you will find! Island Alpaca opened in 2004 as a place for visitors to unwind and relax by spending some time feeding, petting, and yes, hugging all the alpaca your heart desires.


Martha’s Vineyard is a wonderful destination but it is a seasonal destination. Many of the island businesses and hotels are closed during the winter months. And with that, be sure to book your accommodations well in advance if you plan on visiting during peak season.

Travel Tip: It’s an island so expect rain and bring a jacket as it can be a little cold year round.

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