Curator’s statement
Growing up in the suburbs of Boston, going down the Cape or to Nantucket and Martha’s Vineyard was like our version of the Hamptons. While parts of it have changed over the years, its charm has remained, with many sites and restaurants still mainstays. It’s one of my favorite places to go, and I still have family that live across the Cape (from Plymouth to Dennis and Provincetown). It’s the perfect weekend getaway on its own, or as an add-on to a trip to Boston or New York.
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Where to stay in Cape Cod, Nantucket, & Martha's Vineyard
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Things to do in Cape Cod, Nantucket, & Martha's Vineyard
Beaches
Cape Cod, Nantucket, and Martha’s Vineyard each have tons of beautiful beaches. Race Point and Coast Guard Beach have sweeping views, but the former is great for sunsets and the latter is popular with body surfing. Mayflower Beach is perfect for families and exploring tide pools. Cisco Beach on Nantucket is a surfer’s paradise, and Menemsha Beach on the Vineyard is great for swimming and another sunset favorite.
Museums
In Hyannis, visit the JFK Museum about the Kennedy family’s Cape legacy. The nearby Rail Museum is great for families and railroad history fans. Nantucket’s Whaling Museum dives into its maritime past with great exhibits, and the Martha’s Vineyard Museum blends island history, art, and coastal views. For some local & regional art, the Cape Cod Museum of Art in Dennis is a must-visit.
Sites
Cape Cod’s Highland Light (the oldest & tallest on the Cape) and the Pilgrim Monument offer great views. On Nantucket, Brant Point Lighthouse (built in 1746), the Old Mill (the oldest functioning windmill in the US), and the island’s cobblestone-lined Historic District are charming, quintessential experiences. Check out the clay cliffs of Aquinnah and the gingerbread cottages of Oak Bluffs on Martha’s Vineyard. Be sure to ride the oldest platform carousel, the Flying Horses Carousel (brought from Coney Island in 1876), and try to catch a brass ring!
Wildlife
For some of the best whale-watching opportunities, head to Provincetown for daily departures April to October. There’s also great bird watching at Monomoy Refuge in Chatham, Felix Neck on the Vineyard, and Coskata-Coatue on Nantucket. The Woods Hole Science Aquarium is a hands-on favorite for all ages, and the oldest public aquarium in the US.
Biking & hiking
Cape Cod’s Rail Trail stretches over 25 miles from Yarmouth to Wellfleet, perfect for cycling. The Great Island Trail in Wellfleet is home to some of the Cape’s most rugged hiking trails but leads to some beautiful secluded beaches. On Nantucket, there’s over 30 miles of paved bike paths across the island, while Martha’s Vineyard’s Correllus State Forest offers 14 miles of trails for walking or cycling away from the coastline.
Wineries & breweries
Head to Truro Vineyards for Cape-grown Chardonnay or Merlot (they also have a new small-batch distillery making gin and rum). On Nantucket, Cisco Brewers is a lively all-in-one stop for local beer, rotating food trucks and live music (plus on-site Triple Eight distillery offerings and wine from Nantucket Vineyards). Over on Martha’s Vineyard, check out Bad Martha’s microbrewery.
Places to eat & drink in Cape Cod, Nantucket, & Martha's Vineyard
The Nautilus (Nantucket): Asian and Latin twists on seafood that’s tapas-style small plates perfect for sharing. It’s a fun crowd with a great cocktail menu.
Galley Beach (Nantucket): The setting alone makes this a must-stop! Right on the sand, grab a cocktail, stay for the sunset and seafood.
Lookout Tavern (Martha’s Vineyard): This is the go-to casual joint that’s seemingly always packed with some tasty lobster rolls and fish.
Détente (Martha’s Vineyard): Upscale date-night dinner spot without the fuss. It’s cozy with good food and wine.
Water Street Kitchen (Wood’s Hole): A little hidden and totally charming with seasonal dishes, a small menu, and sidewalk seating.
The Skipper (South Yarmouth): A Cape Cod institution since 1936. Lobster rolls, chowder, fried seafood, and soft-serve for dessert, right across from the beach.
Fishermen’s View (Sandwich): Enjoy the deck on a sunny day with super fresh seafood and sushi overlooking the marina.
The Pheasant (Dennis): Set in a restored barn that adds to the charm, it’s a rustic but cool, homestyle dinner with a great cocktail list.
Blackfish Bistro (Truro): Tucked into a little old blacksmith shop, it’s lowkey but elevated seafood, pasta, and meat dishes.
Twenty-Eight Atlantic (Harwich): Found at the Wequassett Resort (which has some other great dining and drinks spots), it’s the perfect upscale, special-occasion restaurant.
Mac’s Chatham Fish & Lobster (Chatham): Quick and casual, grab a lobster roll and enjoy it outside or to-go. They have several restaurant and seafood market locations across the Cape.
Need to know
Much of Cape Cod, Nantucket, and Martha’s Vineyard is seasonal. Many restaurants and hotels operate between April to October (each will vary, though). Expect crowds in peak season, from June through August.
It’s also easy to get to and get around. You can fly into a local airport and rent a car, use public transport, ride-share services, ferries or even rent a bike. It all depends on how much you want to see during your visit.
Double-check which towns the ferries operate to on Nantucket or Martha’s Vineyard.
If you’re driving, there’s only two bridges in or out of the Cape. Parking can also be tricky with small lots and some towns requiring resident permits.
For more inspiration and insider recommendations, visit our Massachusetts page.
Travel Advisor
Rod Carrillo-Lundgren
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