Jetset to Martha's Vineyard with Gray Malin
September 9, 2016
Do you follow Gray Malin on Instagram? We're constantly enamored with his jetsetting ways. His recent trip to Martha's Vineyard proved to be both gorgeous work (see the new collection here!) and and some really fun play. He's dishing up on all the hidden gems on Martha's Vineyard. Check out the must eat, sleep and do's plus get cozy with his signature snaps of the beaches on MV and Nantucket.
Last month, I had the chance to join my cousin on a family trip to Martha’s Vineyard. My grandparents owned a house in Edgartown and my Dad and his four brothers have endless stories growing up going to "The Vineyard." One of my Uncles' even lives there year round to this day! Overall I was really blown away by this beautiful slice of Americana. Together we did a lot of exploring of this uber cute island and it was a treat to experience it from the eyes of my family who have been coming for so many years.

Miacomet Beach, Nantucket

Jetties Beach, Nantucket

Estimated at 100 square miles of land and divided into 6 towns: Tisbury, Edgartown, Oak Bluffs, West Tisbury, Chilmark, and Aquinnah - My cousin, Abby and I covered lots of ground! I spent the better part of the four days interviewing my family for tips so below is a collective guide of my travel tips for anyone looking to plan a vacation to this timeless island.

Aquinnah Umbrellas, Martha's Vineyard

The Couple, Martha's Vineyard


The Harbor View Hotel

This beautiful hotel looks over the light house and has a wrap around porch that is perfect for sipping Bloody Mary's on rainy days.

The Charlotte Inn

In the words of my cousin, Abby, this hotel is "ridiculously cute!"

The Beach Plum

Set on a hill overlooking the Menemsha harbor, this quaint 19th-century inn is a 7-minute walk from the Menemsha village

Rent a House

Lastly, for a larger group, the best way to go is to rent a house, through usual suspects like AirBnB or VRBO, and then there is also HomeAway. This obviously isn't too much of an insider tip but wanted to include nonetheless as this is what we did, and it was so ideal being all together under one roof.

Sunfish Sailboat, Martha's Vineyard

Surfside Beach, Nantucket



This is the part of Martha's Vineyard that I stayed in. It was very easy to bike around and check out all the the shopping and restaurants in the area. Known for their light house, the most iconic beach to visit is Light House Beach, which is also great place to go crabbing!

Oak Bluffs

*In 1866 Robert Morris Copeland was hired by a group of New England developers to design a planned residential community in Martha's Vineyard. The unique "Carpenter's Gothic" architectural style of the cottages was often accented by the owner's use of bright, multi-hue paint schemes, and gave the summer cottages a quaint, almost storybook look. Dubbed "gingerbread cottages," they became a tourist attraction in their own right in the late nineteenth century. And tourists, like myself, still enjoy them today! They are just SO Instagram'able.


Tucked at the western end of Martha's Vineyard, Menemsha is an old fishing town located in the town of Chilmark, which is famous for Alley's General Store and for being where President Obama likes to stay while visiting the Vineyard in Chillmark.

Aqinnah Beach

Famous for the red cliffs and beach, this a MUST see in MV. South Beach Bridge, dubbed The Jaws Bridge at State Beach is perfect for the movie lover in all of us, especially those who love scary movies! Take in some movie magic history and visit the beach where the move JAWS was filmed.

Ocean Rain, Nantucket

Black Lab, Martha's Vineyard


The Bite

This legendary clam shack has tremendous fried oysters and clams

Nancy's Restaurant

(Also known for being Sasha Obama's summer job) has been serving up tasty seafood since the 1960s.

Offshore Ale Company

This is obviously a heated debate but I have to say I really enjoyed my Lobster Roll here and it went down quite nicely with a cold brew.

Scoop Shack

Literally, the best ice cream I've ever had. Cool Mint Oreo was 70% Oreo cookies crunchy and 30% mint chocolate chip ice cream. Homemade daily!

The Atlantic Restaurant

During the day they serve bacon at the bar instead of nuts or other bar snacks. People love it! Then, at night it becomes a big bar scene, it's definitely a happening spot to go anytime of day.

Aquinnah Kayaker, Martha's Vineyard

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