Curator’s statement
Charming coastal towns never seem to go out of style, and Cape Cod, Massachusetts, is no exception. As someone who grew up in Boston, I almost forget that most people are not privy to the magic that is a New England summer. Think historic cottages, boutique hopping, and seaside dining with the best flavors. Cape Cod is the perfect long-weekend getaway for those looking for seaside bliss combined with storied elegance.
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Day 1: Leisure & lobster rolls
Morning
Your first full day in the Cape should be about tapping into your New England energy. Rent a bike and follow the Shining Sea Bikeway for stunning landscapes, cute little villages, and views of the harbor.
Evening
End your day with a classic seafood dinner at Beach House Grill. Think seaside views and perfect golden-hour sunsets.
Day 2: Sip, shop & stars
Morning
Head down to Hardings Beach. This beach is typically quiet in the morning—especially during the late summer—and perfect for a yoga session, a peaceful stroll, or a meditation practice.
Afternoon
Spend the midday sipping, strolling, and shopping along Chatham's Main Street. I would suggest grabbing lunch at Captain’s Table for the best clam chowder and crab cakes. If you have time, make a stop at the Chatham Pier Fish Market for some local treats.
Evening
Grab dinner at La Bella Vita Kitchen & Bar, then head to Marconi Beach for some stargazing sans light pollution. A perfect end to a perfect New England day.
Day 3: Ocean discovery
Morning
Your last day in Cape Cod deserves to be iconic. Charter a boat for a day of sailing in the Atlantic. The best thing is: you have options. If your travel style leans more adventurous, you can take a stab at deep-sea fishing, while the vacationers can charter a yacht with champagne on demand. The Cape is also home to lots of marine life, so whale watching, sea lion spotting, and dolphin sightings are all on the table.
Evening
Enjoy a final dinner at Pepe’s Wharf Restaurant in Provincetown, a seaside restaurant giving major coastal vibes. I recommend ordering the garlic and clam flatbread.
Need to know
Renting a car is going to be the best way to move around the Cape at your leisure. Towns can be further apart than you'd think, so be sure to plan ahead!
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For more inspiration and insider recommendations, visit our Cape Cod page.