The ultimate guide to Cape Cod, Martha's Vineyard and Nantucket

Taking a bite out of a hefty lobster roll, picking seashells along powdery beaches and watching fireworks — nostalgic memories for many Americans who spent their summer vacations visiting these quintessential locations. Steeped in history, Cape Cod was the site where the Mayflower Pilgrims first docked in 1620 and has been the preferred summer retreat for many American presidents. This pocket of Massachusetts comprises the hook-shaped peninsula of Cape Cod, along with the neighbouring islands of Martha’s Vineyard and Nantucket. From scenic bike trails and nature reserves to seafood shacks and boutique shopping, here’s a guide for how to make the most of your visit.

Cape Cod

With its hilly dunes, pristine shorelines and salty sea breeze, Cape Cod has offered a welcome respite for those looking to escape the hustle and bustle of city life since the 19th century and, over the years, became the muse of literary legends like Henry David Thoreau and Eugene O’Neill. While the beaches are the main draw, other highlights include the many museums, nautical-themed boutiques, art galleries, historic lighthouses and restaurants serving freshly caught seafood.

Cape Cod is made up of 15 towns, and at the tip of the peninsula, Provincetown is where it all began. The site of the Mayflower’s first landing, Provincetown has served as the home of the Nauset tribe, a fishing and whaling hub, and an LGBTQ-friendly artists’ colony. For a sweeping view of the town, visitors can climb the 252ft Pilgrim Monument, the tallest all-granite structure in the US.

The oldest town on Cape Cod is Sandwich, settled in 1637. Its historic district features the still-working Dexter Grist Mill, as well as the Hoxie House, one of the oldest surviving houses in Massachusetts. Nature enthusiasts can wander through the 700-acre Shawme-Crowell State Forest, which has 15 miles of hiking trails surrounded by pitch pine and scrub oak.

At the elbow of Cape Cod, Chatham is a quaint New England fishing village with a picturesque main street, a 48ft-tall lighthouse and seafood restaurants like the popular Mac’s Chatham Fish & Lobster. Further up the coast is the Cape Cod National Seashore, home to scenic hiking trails, six swimming beaches and historic sights that stretch out along 40 protected miles of coastline. 

In Mid Cape, Hyannis is the main departure point for ferries to Martha’s Vineyard and Nantucket. Here, visitors can learn about the 35th president’s connection to Cape Cod at the John F. Kennedy Hyannis Museum or delve into the region’s nautical traditions at the Cape Cod Maritime Museum. Before catching the ferry, don't miss the chance to feast on some fried clams or clam chowder at Spanky’s Clam Shack.

Martha’s Vineyard

Martha’s Vineyard is a storybook time capsule of small-town charm, regal Gothic Revival homes, cheerful ice cream shops, rolling hills and pristine coastlines. Just seven miles off the coast of Massachusetts, the Vineyard — as it’s often called — is a triangular-shaped island made up of six towns, each with a distinctive personality.

The largest is Edgartown, an old whaling port with streets lined with boutiques, art galleries, restaurants and the former homes of whaling captains, merchants and prominent local families. Four miles northwest of Edgartown is Oak Bluffs, a popular stop for day-trippers who come to have a leisurely picnic at the grassy Ocean Park. Here, visitors can take a whirl on an antique carved wooden horse at the Flying Horses Carousel, the oldest platform carousel in the nation, and take photos of the multi-hued Gingerbread Cottages at The Campground.

Between Edgartown and Oak Bluffs is the famous ‘Jaws Bridge’, which featured in the 1975 film Jaws. Visitors can get a behind-the-scenes insight into the movie and then delve into the island’s history at Martha’s Vineyard Museum in Vineyard Haven, the town centre of Tisbury. In the summer, the farmers’ market in West Tisbury is abuzz with vendors selling jams, dahlias, fresh produce, cheese and artisanal bread.

A visit to Martha’s Vineyard wouldn’t be complete without a stop at Aquinnah, on the island's western end. Here, guests can learn about the stories of the Aquinnah Wampanoag tribe at the Aquinnah Cultural Center, see the 1799 red-brick Gay Head Lighthouse and marvel at the craggy red-clay Aquinnah Cliffs.

Nantucket

While Nantucket has a reputation for being the playground of the rich and famous, the island’s unspoiled beaches, scenic hiking trails and historic sites make it the ideal escape for those seeking a laid-back break. Nantucket exudes quiet luxury with its cobblestone Main Street, grand Greek Revival houses, curated boutiques and fine dining restaurants. But venturing beyond the main thoroughfare, visitors will discover a landscape of rolling hills, rugged pastures and miles of sandy beaches. Surfers favour the bigger waves at the aptly named Surfside Beach, as well as Nobadeer Beach, while families with little ones prefer paddling around the shallow waters at Jetties Beach.

One of the best ways to explore Nantucket is on two wheels, through a network of more than a dozen bike paths. After snapping a photo of the 26ft-tall wooden Brant Point Lighthouse, pedal to the 1686 Jared Coffin House, one of the oldest residences on Nantucket, and then head to the Old Mill, one of the oldest operating windmills in the country.

For a more challenging cycle, visitors can take the 8.7-mile Polpis Bike Path with stops at Altar Rock, the Nantucket Shipwreck & Life Saving Museum, the Windswept Cranberry Bog and the red-and-white Sankaty Head Lighthouse. You can stop for a refreshing beer at Cisco Brewers, where there’s also live entertainment plus food trucks selling lobster rolls and oysters. Round the day off by toasting the sunset at the harbour-side Straight Wharf Restaurant, dining on even more — you guessed it — deliciously fresh seafood.