4-Day Weekend in Cape Cod: Beachcombing, Island Hopping, and New England-Style Eats

Cape Cod—that slender curvature of Massachusetts coast and its famed pair of isles, Nantucket and Martha’s Vineyard, epitomize “away” like no other escape valve on the upper Atlantic shore. Since the late 1800s, droves of summer vacationers have been bewitched by this area—its ageless miles of seagrass studded beaches, clam shack roads, and classic coastal towns from Falmouth to Provincetown beckoning like a flexed arm. Every lighthouse here tells a story, as does the eponymous architecture—epitomized by those tidy, single-story cottages with their impossibly steep roofs.

The Cape, Nantucket, and Martha’s Vineyard jointly represent a serene departure from urban life. The shingle-style buildings are human-scale, life moves at a slower pace, and the uncannily beautiful light has inspired generations of artists. Steeped in nautical motifs, here’s your small-town Americana with a coastal New England twist. Cape Cod is truly a charmed, beloved place for everyone these days—not just the rich, recognizable, and well-heeled (though you’ll still find plenty of them out here, too).

Where Is Cape Cod?

Cape Cod (aka “the Cape”) is a hook-like peninsula located southeast of Boston that takes about an hour and 20 minutes to reach by car from its closest major city. Driving to Provincetown, the tip of the Cape, and its most vibrant village, takes another 40 minutes. Along the way, you’ll hit such charming spots as Wellfleet and North Truro. Many people opt to travel by sea. Several ferry lines run from Boston Harbor to Provincetown, and take around 90 minutes.

A pair of rarefied vacation islands, Martha’s Vineyard (just call it “the Vineyard”) and Nantucket, lie south of Cape Cod—with the Vineyard much closer to the mainland and Nantucket more far-flung. Either can be reached via passenger and car ferry from the mainland. Ferries also run between the two islands.

Best time to Visit Cape Cod

Summer is high season on the Cape, with generally moderate, breezy temperatures that are warm enough for swimming when much of the country is a sweaty caldron. July can be somewhat busier than August, but June can be lovely as well. Those in the know hold out for September when the kids are back in school and the weather is blissful. Visitors seeking quiet and the changing of the leaves will push their vacations later into the fall.

Where to Stay in Cape Cod, Nantucket, and Martha’s Vineyard

Edgartown Collection, Martha’s Vineyard

Composed of five hotels—Christopher, Richard, Sydney, Coco, and Edgartown—positioned just blocks from each other in the center of the Vineyard’s most beautiful town, the Edgartown Collection is long on charm. Inside, you’ll find canopy beds and waffle kimono robes; outside, lounge beside a fire pit. Enjoy a homespun continental breakfast (coffee, fruit, overnight oats, homemade sweet and savory pastries), before you set out for the day.

The Red Inn, Provincetown

This landmark hotel and restaurant, which was built in 1805, epitomizes the West End—away from the day-trippers. It’s a those-in-the-know kind of place, where devotees return every summer for cocktails on the lawn facing the harbor. If you’re able to snag one of the prized half-dozen individualized suites, you’ll enjoy easy access to the beaches and bike trails. The Monument View Suite takes in the vista starring Provincetown’s Pilgrim Monument; the Chauffeur's Cottage boasts a seaside deck. Or you can splash out the tri-level Delft Haven Residence, with its deep soaking tub and baby grand piano.

The White Elephant, Nantucket

This shingle-style complex rose up in the 1920s—100 years later, the White Elephant manages to quietly dazzle with its brand-new restoration. Though it commands a great deal of prime real estate in Nantucket’s main town, it blends in seamlessly, with a range of accommodations to suit every preference, from rooms and suites in the main inn or Harborside Hotel to discreet cottages to tricked-out lofts for families or multiple couples. You can swim laps at the pool house or set up on the sandy beach just steps from the hotel’s verdant lawn. Dine inside or out at the Brant Point Grill, the White Elephant’s all-day dining venue.

What to Do on Cape Cod and the Islands

Cape Cod is one of the best places to bike in the country, with routes through and between the towns, plus sloping trails in the dunes. The area is also catnip for pedestrians. Quaint galleries proliferate for art hoppers, especially in Provincetown, and excellent cuisine is plentiful—not just the region’s famed lobster rolls and New England clam chowder, but also baked goods, artisanal ice cream, and more elevated dining. The Cape and the islands also boast sandy, picturesque beaches and charming rental cottages, where folks happily while away the afternoon rocking on a porch with a bottle of wine and delicacies from one of the many general stores and farm stands.

Day 1: Savor the Flavors of Provincetown

There’s no place on earth like Provincetown. “Ptown is magical,” says Joe Bruno, a hair stylist who moved to North Truro permanently from Los Angeles and opened Bruno’s Chop Shop on Ptown’s colorful Commercial Street last April. “I always wanted it to be my ‘end up’ place. It’s very accepting and nurturing.”

An epicenter of the LGBT+ community and a touchstone for visual and performing artists for generations, this was the hideaway that nourished everyone from playwright Eugene O’Neill and painter Jackson Pollock to today’s most outré drag performers. When walking along Commercial, a block from the sea, it’s not unusual to spy screenwriter and playwright Tony Kushner (Angels in America, Lincoln, The Fabelmans), actor Murray Bartlett (The White Lotus, Welcome to Chippendales), novelist Michael Cunningham (The Hours), or political pundit Andrew Sullivan.

Ptown quickly seduces all comers of all stripes. If you’re just visiting for the day, get here early as you’ll want to fit in as many meals as possible. Provincetown grub is that good. Locals and tourists line up at The Canteen for its raw bar, hot and cold lobster rolls, and an addictive grilled cheese sandwich lavished with cheddar, smoked Gouda, Gruyere, and Parmesan on sourdough bread. It’s pretty difficult to leave The Canteen’s patio and vast bayside garden once you’ve scored a table, but your rental bike is calling.

Pedal to the West End, the town's tip—which curls around, so the edge of Provincetown is actually west, not east. It’s a rite of passage to walk along the rocky breakwater that extends into the bay. “Walk halfway out and just take in the world,” Bruno advises. Then, hop back on your bike to take in the views of coastal marshes that catch the area’s famously ethereal light, which crescendos at stunning Herring Cove Beach with its golden sands and cool waters. Awol Hotel (formerly Inn at the Moors) is perfectly situated across the street from the shimmering marshlands—boasting a heated pool and fire pits.

From here, it’s a short walk to the Red Inn, where it’s de rigueur to meet up for cocktails (the Summer Manhattan and the Tea-tini are favorites) and dinner. Owner Philip Mossy has owned the Red Inn for 22 years and says that patrons can’t get enough of the Wellfleet oysters, pan-roasted cod, and smoked duck.

Day 2: Meander Down the Cape and Hop a Ferry

For breakfast, Provincetown Portuguese Bakery, smack in the middle of Commercial Street, is an institution for its malasadas (sweet fried dough) and rabanadas (Portuguese French toast). As you meander through town, be sure to take in at least a few of Ptown’s galleries. Woodman Shimko Gallery is a mainstay with frequent openings where collectors mingle with glasses of wine among the home accessories and the popular Hank Hudson digital designs on canvas.

Continue east along Shore Road—by bike, bus, taxi or even pedicab—and you’ll reach quiet North Truro, which has a gently curving beach and, facing it, 22 identical, green-shuttered cottages all named for flowers. You may want to pick up provisions for a picnic on the sand. For that, there’s Days Market & Deli (great soups, smoothies, poke bowls), or you can continue on to Highland Road to explore what passes for North Truro’s town center. There you’ll find yet another impressive deli, Salty Market, which produces insanely good roast beef sandwiches and brisket tacos. What’s for dessert? You’ll find more tough decisions at Chequessett Chocolate and High Tide Kitchen, an ice cream truck where you can order quirky combinations like coffee mud pie on a birthday cake cone topped with unicorn sprinkles.

If you can’t get enough of the Outer Cape (and who can?), continue south to the nearby town of Wellfleet, the original location of famed market Mac’s on the Pier (there’s a Mac’s in Ptown as well), where you can choose a picnic table and devour the town’s namesake oysters and littleneck clams.

Hyannis Port is about 35 miles down the road (about an hour’s drive) where you can hop a ferry, with or without a car, to Nantucket. Check into the White Elephant. It’s the most luxurious hotel on the island, with a sublimely personable staff overseen by general director Bernhard Duerrmeier. You can book a suite at the main inn with a terrace overlooking the harbor, a private garden cottage, or a 3-bedroom downtown loft a few blocks away. A helpful staffer will set you up on a bike, so you can pedal the few blocks downtown to sample the chocolate peanut butter cookie dough ice cream at the Juice Bar, which sometimes draws lines down the block.

Hopefully, that hasn’t spoiled your appetite, as the White Elephant’s Brant Point Grill is sure to serve up a knockout dinner. Treat yourself to a specialty cocktail, like the ACK Sunshine, concocted with Ketel One peach and orange blossom vodka, pineapple, and lemon, before tucking into a dinner of avocado and cucumber gazpacho with Alaskan king crab and shaved caviar—and the restaurant’s outstanding lobster mac & cheese, made with rigatoni and Vermont cheddar.

Day 3: Nosh Through Nantucket

Swim it all off the next morning over some laps in the White Elephant’s sun-splashed pool. Then arrange to visit the hotel’s sister property, Wauwinet, the island’s sole Relais & Châteaux property, which is more remote. Now that you’ve worked up an appetite again, breakfast is the perfect excuse to check out Wauwinet’s restaurant, Topper’s. Order the decadent cinnamon roll French toast with caramel apples, candied pecans, and cream cheese frosting, then settle into a plush wicker lounge chair on the lawn facing the tranquil waters of Nantucket’s northeast coast.

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Once back at the White Elephant, walk or bike around the heart of Nantucket, which is stuffed with character. Centre Street is the place to admire contemporary art—specifically at Sam Owen Gallery, featuring the colorful “drip” paintings of Gian Garofalo. A few doors down is Born & Bread, where you can snag a few Nutella Cruffins for the trip over to Martha’s Vineyard.

The high-speed catamarans take about an hour to cross Nantucket Sound, pulling into Oak Bluffs, which is well-known for its fanciful gingerbread cottages. Lark Hotels, a boutique chain, is well-represented on the Vineyard. If you want to be close to the ferry, Summercamp—which harkens back to an idyllic summer childhood of badminton and board games—is just a few minutes’ walk to the disembarkation spot. The multi-building hotel is also conveniently close to a row of casual raw bars and grills, including the Shuck Shack and the Sand Bar, and a heavenly strip of sand and crystal-clear waters south of the ferry pier.

The real name of the game in the Vineyard is Edgartown, the island’s historic, upscale town where the five hotels of the Edgartown Collection still evocatively hold court. Edgartown is absolutely captivating, with its live music spilling onto cobblestone streets lined with hydrangea-festooned homes, bookstores, boutiques, and fudge shops. Of course, this place is a refuge for presidents. The Clintons summered here, as did the Obamas, who purchased a 29-acre estate on Edgartown Great Pond in 2019 for $11.75 million. Dinner choices abound in town. Chief among them is Atria, where the plancha-seared George Bank scallops with curried carrots are top-notch.

Day 4: Vanish on Martha's Vineyard

From Edgartown, hop on your bike in the morning to experience the island’s bucolic side. It takes less than 10 minutes to make it a bit inland to Morning Glory Farms, where the breakfast items, baked goods, and soups rotate daily. On a recent morning, walnut jam bars, salted honey pies, and lemon ginger scones were on the menu. Founded in 1975, Morning Glory uses its 70 acres to grow vegetables, herbs, flowers, and summer fruit. So, fill up a bag with strawberries, peaches, and beach plums—and pedal onward.

In less than 20 minutes, you’ll find yourself at one of the longest, broadest, and most appealing beaches you could ever casually roll upon. South Beach occupies the bottom line of this triangle of an island. Here, you can walk (and walk) and find perfect solitude. Every once in a while, a local sitting on a beach blanket will wave to you and smile. That’s the Vineyard. Lots of dough, but no attitude.

Soon you’ll be checking your phone to make sure you’re on the last possible ferry back to reality.