I’ve always heard about how beautiful summers are in Martha’s Vineyard, but until this weekend, I’ve never truly grasped the magic of the island – imagine this: quaint gardens, unassuming elegance, and incredible charm around every corner.

To my surprise and delight, every home on island was architecturally and color coordinated (cue my glee!), but my happiest discovery was how absolutely picture perfect the yards were; every neighborhood was a curated beauty of hydrangea, lilies, and bright green grass. 

Grey is THE color on island, and shingle style homes are the prominent architectural style – brought in the 1600’s by the first European settlers.

Almost every home is a shade of grey with white trim, white picket fence, and beautiful lawns overflowing with flowers. It makes for incredibly charming and picturesque neighborhoods all over island.

One touch I noticed, and loved, was the American flags flying in homes and all around town.

Martha’s Vineyard is a similar size to St. Croix (the island I grew up on in the US Virgin Islands) making it feel quite homey. While we have only 2 towns, Martha’s Vineyard has 6 dotted around the island, all architecturally reminiscent, but each having developed their own personality.

Here are some of the highlights of each town:

  1. Edgartown: The Historic Town, Harbour, & Harbour Lighthouse
  2. Oaks Bluff: Gingerbread Homes & Flying Horse Carousel
  3. West Tisbury: Grange Hall (Farmers/Artisan Markets)
  4. Aquinnah: Gay Head Cliffs & Lighthouse
  5. Chilmark: Rolling Hills & Menemsha’s Fisherman’s Village/Beach
  6. Tisbury/Vineyard Haven: Scenic Harbour & Main Street

It was an unassuming, idyllic weekend spent in Martha’s Vineyard.

Early Saturday morning we stumbled upon a rustic Farmer’s Market at Grange Hall in West Tisbury on our way to the cliffs in Aquinnah.

There was live music, baskets overflowing with local produce, children playing in the field, and homemade goodies galore; it felt as though the entire island had convened together on this sunny morning, at this historic hall, all for this beautiful moment in time.

I took my time idling over the most beautiful bundles of pink stargazer lilies, couldn’t resist the scent of freshly baked bread, stood in the longest line for Vietnamese spring rolls, and gazed longingly at the locally produced honey, chocolate, and scones. Of my samplings, the jalapeño jam on a cracker was my favorite. 

I don’t normally play favorites when I travel, but of all the towns, Edgartown and Menemsha were where I enjoyed my time the most.

The summer days were long, salty, and spent on the sea, and when the evenings cooled off, sitting in the harbor was the perfect place to sip rose and watch the long rays of the sun set over the deep blue sea.

Where To Stay:

I found Edgartown to be the most charming of them all, and based on what I heard from the locals, I would recommend staying in the Charlotte Inn.

What To Pack:

I love to be inspired by the place I’m visiting, mixing and matching pieces from my closet until I sense the feeling of the destination is properly translated into my own style.

Martha’s Vineyard, with all it’s historic grandeur, has a decidedly irresistible air of casualness. It’s an island of understatement. 

Plan on leaving behind all your flashiest clothes, and focus on casual elegance. With classic lines and preppy details, you can never go wrong for any occasion. 

Depending on the time of year you are visiting, there could be a crispness in the air, and I found layers to be the key to comfort on both land and water.

Here are a few key pieces to consider while packing:

The White Shirtdress:

The One-Piece:

The Breton Stripe Sweater:

The Flowy Summer Dress:

The Woven Essentials:

Mix & Match Pieces:

What To Do:

Lighthouses: Explore all the lighthouses the island has to offer, from Edgartown to Aquinnah. They are in picturesque locations, my favorite being the lighthouse overlooking the cliffs in Aquinnah.

Farmer’s Markets: Spend the morning leisurely wandering the local artisan/farmers’ markets, nibbling on homemade pastries, sampling lavender honey, sipping iced coffee, and chatting with the neighbors. 

Boating: Spend the afternoons on a boat with friends, or if you’re renting a home with friends by the sea, put on a good playlist, prepare a round of fruity inspired summer drinks, and enjoy spending time with your besties in and around the harbour swimming, sailing, and sunbathing.

Chappaquiddick Island: Take the Chappy Ferry from Edgartown to this rustic island. Relax on the beach or visit the Japanese gardens.  

Town Hopping: Visit the 6 famous towns: Edgartown, Oaks Bluff, Vineyard, Aquinnah, Chilmark, and Tisbury – each with something unique to offer.

Where To Eat:

Martha’s Vineyard is filled with beautiful farm land. The fruit and vegetables on island are fresh, abundant, and most importantly – delicious!

There are so many options, either inland or along the coast, but of the places I tried, I recommend these two:

Mad Martha’s: Indulge in homemade ice cream at Mad Martha’s (try the blueberry ice cream!) 

Rosewater Market: A cute cafe with beautiful outdoor seating and a delicious menu.

All in all, this was one of the most beautiful, laidback weekends I’ve ever experienced in the Northeast, perfect for friends and family getaways – and I truly look forward to my next visit with my family!

Xx, CC