Explore the Towns: The Island is made up of a variety of unique towns, each with their own personality. We LOVE them all… just depends on your taste. Visit Chilmark, home to the towns of Menemsha & Aquinnah, for the most authentic experience full of stunning views & sunsets. Edgartown & Oak Bluffs are the most happening with lots of dining (only non-dry towns on the island) & activity options. Best advice- remember it’s an island… so when in doubt, just keep circling.
Beaches: Bask in the sun in one of beautiful, secluded beaches. If staying in Edgartown, South Beach is the most popular. Hidden gem: venture on a 20-minute bike ride to the south shore for Long Beach (Long Point Wildlife Refuge)… it’s well worth the views of the Atlantic Ocean and freshwater pond. Get the full beach scoop here.
Gay Head Clay Cliffs: The multi-colored clay cliffs at the western end of the island (Aquinnah) are a must see. The Gayhead Light, the first lighthouse on Martha’s Vineyard, and beautiful vistas make for THE perfect photo-op. Rainy day? Even better. The clay from the cliffs turn the water our favorite color- PINK.
Chilmark Chocolates: Stop by the famous chocolate shop to satisfy your sweet tooth. The tiny shop can only accommodate about 10 people at a time but is WELL worth the wait. Our favorite: the milk almond crunch.
Flying Horses Carousel: Head to Oak Bluffs and take a ride on the nation’s oldest platform carousel. Make sure to take a stroll around Oak Bluff’s adorable “gingerbread houses” that have carousels carved into the woodwork afterwards.
#BuyMeLilly: Visit our friends at In the Pink in Edgartown for your Lilly fix.
Larsen’s or Menemsha Fish Market: The highlight of our trips to Martha’s Vineyard is always the Menemsha sunset. Walk in and order your favorite seafood from Larsen’s or Menemsha Fish Market and sit on the beach with a bottle of wine (BYOB) while watching the sun set over the glistening ocean. It’s truly an unforgettable experience.
L’Etoile: Stylish & intimate, L’Etoile is the perfect spot in Edgartown to have a relaxing dinner. Looking for a spot for cocktails before dinner? Order a Startini at their Star Bar.
Port Hunter: Stop by this vibrant venue for a fresh meal & a craft beer with live music. There’s a different menu every day and many ingredients are grown in their garden right in the backyard.
The Seafood Shanty: Located in downtown Edgartown, this restaurant’s patio has the best views of the waterfront. Try to score a seat on the rooftop deck for a casual lunch.
Chowder Company: This local fish house & raw bar in Oak Bluffs has the best chowder on the Vineyard. THE. END.
Artcliff Diner: Our favorite breakfast spot… expect the full 1960s diner experience with mismatched glasses and all. It’s the perfect place to grab breakfast before heading to the Vineyard Haven ferry to hop to another island.
Back Door Donuts: Nestled just off the main path in Oak Bluffs is HEAVEN. Visit this hole-in-the-wall bakery after a night on the town for dessert. The line can be quite long at times but helloooo apple fritter.
Harbor View Hotel: Our #1 recommended place to stay on Martha’s Vineyard. Located in the heart of Edgartown, the historic hotel overlooks the Edgartown Lighthouse. All generations will enjoy the property & stunning ocean views.
Kelly House: A registered historic hotel of America, the homey Kelley House in Edgartown is another option. Stop by The Newes, the hotel’s pub, for lunch paired with limited-release New England beers.
You never know what the weather will be like on Martha’s Vineyard. So prepare for everything with easygoing pieces that take you from morning shopping to the beach to dinner. The Lilly Pulitzer Dusk Strappy Silk Slip Dress or the Captiva Tunic Cover-Up are the perfect go-to styles. Make sure to stop by In the Pink in Edgartown to be fully outfitted!