Sunday Manifest: Martha’s Vineyard

Lovingly called “The Vineyard” by locals, Martha’s Vineyard has long been the summer vacation destination of choice for ex-presidents and other celebrities looking for a quiet coastal getaway. Don’t be surprised if you run into Bill Murray having lunch at an outdoor café or Ted Danson and Mary Steenburgen taking in a show at the Martha’s Vineyard Playhouse. You may even find yourself vacationing alongside island regulars such as David Letterman, Spike Lee, and members of the Kennedy and Obama families.

What they and other visitors know is that this quintessential New England destination, located on the southeastern coast of Massachusetts, is a true northeastern island paradise. Less crowded than nearby Cape Cod, but just a short ferry ride away, The Vineyard has everything you want from an upscale coastal community—charming cottages, historic lighthouses, high-end boutique hotels, family-friendly beaches, and clear blue water that’s perfect for swimming and sailing during the warmer months. 

Photo: jo Crebbin/Shutterstock

The 96-square-mile island is roughly divided into two very different regions, dating back to its whaling days. There’s up-island (and the small towns of West Tisbury, Chilmark, and Aquinnah) and down-island (home to Edgartown, Vineyard Haven, and Oak Bluffs).

Up-island, which is actually the western part of Martha’s Vineyard, has a rural, remote feel, with a lush landscape of rolling hills and forests dotted with small farms, general stores, and homes that are more spread out. It’s the best part of the island to visit if you want to get away from the action, buy local farm-fresh produce, or walk the landmark Aquinnah Cliffs.

Down-island, along the eastern coast, boasts a more sophisticated New England vibe. The towns here feature bustling main streets and downtown areas and a near-endless list of things to see and do (all within easy walking or biking distance), making it a perfect home-base for a Martha’s Vineyard vacation.

The vibrant, historic harbor town of Edgartown is a particularly nice place to stay. Home to picture-perfect houses, high end art galleries, upscale shops, incredible restaurants, and perfectly preserved Cape Cod architecture, it’s both elegant and accessible, and puts you in the heart of the action.

Fans of Stephen Spielberg’s 1975 blockbuster, Jaws, may recognize Edgartown as one of the main shooting locations for the movie. Standing in for the fictional town of Amity, many iconic landmarks captured in the film can still be seen here today. Several local tour companies offer walking Jaws tours through the town, pointing out where all of your favorite scenes were shot and sharing details about the production. These unique tours are a fun, family-friendly way to explore the area on foot while getting a behind-the-scenes look at a legendary movie.

Photo: Aubrey Odom-Mabey/Unsplash

When you’re ready to hit the beach, there are several to choose from, each with something different to offer. July through September are the best beach months for anyone wanting to swim on Martha’s Vineyard, but visitors can enjoy time along the shore during other months as well.

The family-friendly Joseph Sylvia State Beach is the one to visit if you want to spend your summer days playing in the water. Here, you can swim, go kiteboarding, or try windsurfing. There’s free parking, calm water, and two miles of white sand to enjoy. Just be sure to get there early and reserve your spot since it can get crowded later in the day.

Katama Beach, often called South Beach because of its location on the island, is a popular three-mile public beach known for its turquoise water and sweeping sand dunes. It’s a hot spot for surfers due to its rough surf, but also attracts swimmers who tend to hang out at its protected, salt-pond side where the waters are calmer.

Lighthouse Beach, a great gathering spot for vacationers looking for a quieter beach day, is just a 10-minute walk or bike ride from most downtown Edgartown hotels. A short sandy path opens to a wide beach with calm water and a scenic lighthouse, making it perfect for picnicking, swimming, or fishing.

For more fun and adventure on Martha’s Vineyard, consider renting a bike during your stay or sign up for a scenic, guided bike tour. Visit the local museums—Cottage Museum, the historical Martha’s Vineyard Museum, and the Vincent House Museum are excellent options. Or charter a boat for an exhilarating sailing cruise around the island.

Photo: christopher781/Shutterstock

You should also find time to visit the stunning Menemsha Hills, a 211-acre nature reserve known for its diverse plant habitats. You’ll see wetlands, woodland groves, and low, marshy landscapes here, and it’s a wonderful spot for a leisurely hike or simple picnic. If you’re not afraid of heights, climb Menemsha’s 308-foot high Prospect Hill, with vistas that span the rugged shoreline of the cliffs of Aquinnah and across the Vineyard Sound to the Elizabeth and Normal Islands. 

You can also visit Chappaquiddick Island’s 18 square miles of beaches, salt marshes, and coastal inlets. This small, secluded part of Edgartown is great for walking, kayaking, fishing, and bird watching.

For meals, we recommend lunch at The Terrace at Charlotte Inn, an elegant bistro-style restaurant located in a beautifully updated Edwardian home in Edgartown Village. Whether you dine in the light-filled conservatory or outdoors on the spacious stone patio, it’s a lovely place to relax between shopping and sightseeing. Atria (also in Edgartown) is a great spot for a sophisticated dinner, and features an extensive wine list, cozy dining room and brick cellar bar, and a seafood-focused menu that changes seasonally. And, for more casual fare, Little House Café in Vineyard Haven is an excellent eatery serving fresh, innovative dishes for breakfast, lunch, and dinner, as well as a variety of baked goods and coffee—perfect for dining in or getting it to go.

Our Manifest team has put together a fabulous five-day trip to Martha’s Vineyard, which you’ll find on our Experiences page. But if The Vineyard isn’t on your vacation wish list, we’re always happy to curate a custom trip for you wherever you’d like to go.