For decades, Martha’s Vineyard has proven to be a worthy opponent to The Hamptons when it comes to Northern summer retreats. You could find Jackie Kennedy water skiing on the open water back in the 70s, or in recent years catch Barack Obama eating ice cream from Mad Martha’s. Princess Diana even made a visit for a fortnight back in the 90s, and Oprah favors this Massachusettian island as well. Regardless of the noteworthy names that frolic the vineyard, I’ll break down what to do while you’re enjoying MV for yourself (photos included). 

 

Where to Stay

Hob Knob Hotel

Nestled in Edgartown (Vogue’s favorite area of Martha’s) is this luxury boutique hotel and spa has hosted guests for nearly a century and allows visitors to fully immerse themselves within the vineyard lifestyle. It’s located a stone’s throw away from the village of shops and restaurants and is worth the stay. Even President Kennedy has stayed here! 

 

The Charlotte Inn

This quaint, Edwardian-style boutique hotel is where Princess Diana chose to stay while in Martha’s Vineyard. The owner of the inn, Gery Conover, and his son, Tim, were able to make her stay as paparazzi-free as possible, and she was so grateful for the peaceful vacation, she threw a thank-you party for the duo. The Inn is just outside of Edgartown, offering luxury and the perfect amount of seclusion. Whether you spend your time sitting within the Inn’s private gardens or having tea in an English sitting room, you’ll find yourself in utter peace, as did Lady Di. 

 

Summercamp Hotel

Nestled in Oak Bluffs (my favorite area of Martha’s) is the uber chic and playful Summercamp Hotel. This place to rest your head perfectly mixes rustic, retro, and nostalgic aesthetics all while being perfectly located in the heart of town. 

 

Where to Eat & Drink

Behind the Bookstore

This charming eatery serves a plethora of coffee and specialty coffee drinks alongside their all-day food menu. It’s tucked away behind Edgartown Books (hence the name) and encourages guests to enjoy their delicious pastries and Orange Thyme Lattes on the lawn while diving into a new novel. 

 

Toccopuro Coffee

There couldn’t be a more picturesque cafe when it comes to Martha’s Vineyard. You’ll find bicycles parked out front as people rush in and out with to-go cups covered in their baby blue, ocean-themed branding. Grab a muffin and your drink of choice and walk towards the water for the perfect afternoon. There are locations in both Oak Bluffs and Edgartown. 

 

L’etoile Restaurant

This chef-owned and operated French restaurant and bar focus on seasonal dishes in a “casually elegant” atmosphere. Their menu is innovative, fresh, and aims to showcase the flavors of the ingredients in the best way possible. Don’t forget to stop by the bar before or after your meal for one of their specialty cocktails like L’etoile’s infamous “startini.”

 

Black Sheep

This restaurant is the perfect spot to stop if you’re looking to have a gourmet oceanfront picnic. While you can, and should also dine in, many of their dishes are prepared to be taken away well, allowing for an exceptional snack while beaching at Chappaquiddick Island. 

 

The Terrace at Charlotte Inn

For an upscale dining experience that transports you to an English garden with French cuisine, look no further than The Terrace at Charlotte Inn (you may even be staying here)! Each menu item can be expertly paired with a glass of wine from their curated selection, ensuring nothing short of an elegant evening (with top-notch service). 

 

Dos Mas

The sister restaurant to Taco Martha’s Vineyard (formerly known as Backyard Taco), offers delicious authentic tacos alongside other fan favorites like yucca fries, vegan nachos, and their scrumptious house chips. Their homemade corn tortillas are not to be passed up, and I’d recommend getting your meal to-go and eating it on a blanket in the center of Ocean Park. 

 

Back Door Donuts

An (un)well-kept secret and a staple to Oak Bluffs. Open solely in the evenings, this daytime bakery shuts its front doors and works out of the door in the back parking lot to provide what could easily be dubbed the greatest donuts I’ve ever consumed, along with incredibly large (and delicious) apple fritters. The line will be long, but it will move fast. Don’t fret, and don’t knock it until you try it. 

 

Where to Shop

Lululemon

I know what you’re thinking, but this Lululemon is worth the trip if you love their athleticwear. Why? Because they’ve got Martha’s Vineyard branded items you can only purchase at this location! Now you’ve got the opportunity to snag a souvenir you’ll wear more often than most. 

 

The Black Dog

An “if you know, you know” situation. Everyone who spends time in Martha’s Vineyard has a Black Dog sweatshirt or two (or seven). You simply can’t leave the island without one– it’s an unwritten rule of sorts. 

 

Chilmark Pottery

Everyone that has a permanent or summer home in the vineyard has more pieces from this gem of a store than they’d like to admit. Almost all of the pottery for sale is made on-site by the master potter, Geoffrey Borr. I had the most insightful and inspiring conversation with him whilst browsing the space and even got to feel raw porcelain in my hands. A truly magical experience, and is not one to be missed. 

 

CB Stark Jewelers

The unofficial supreme jeweler of the island. Known for their silver and gold Martha’s Vineyard-related pendants, you can find anything from the shape of the island to a cup from Mocha Motts to adorn your neck or wrist. You can also find well-known designers like John Hardy and Lika Behar in-store as well.