For a dynamic culinary and arts scene—not to mention a bevy of cocktail bars and an epic Pride celebration—consider Provincetown on the Upper Cape. Chatham, on the Lower Cape, is a quieter option known for its beaches and wildlife. The two are about an hour apart, so it’s feasible to visit locales in both towns.
A blend between a bed and breakfast and a boutique hotel, The Salt House Inn’s charming 1850’s structure boasts rustic wood beams and nautical décor. Lounge with a book in the garden or explore town on one of the complimentary bikes.
Check into Chatham Bars Inn, a historic 217-room seaside retreat with an adjacent golf course, tennis courts, and a private beach. Hop aboard the Bar Tender, part of the inn’s private fleet, for a morning harbor cruise and stroll around the eight-acre farm that grows produce for the two on-site restaurants, The Sacred Cod Tavern and Stars.
In Provincetown, start the day at Chach, a go-to for all-day breakfast and weekend brunch. Order their feta, spinach, and mushroom omelet, huevos rancheros, or homemade granola with vanilla yogurt and fresh fruit.
For lunch, head to The Canteen, a traditional New England–style eatery housed in a 200-year-old building. Select from an array of coastal-inspired dishes made with seasonal ingredients like clam chowder, a succotash grain bowl, and lobster rolls—prepared with lobsters shucked by hand that day.
Stroll along the Provincetown art walk, where galleries open their doors to the town from 6 to 9 p.m. Then, dine at PB Boulangerie Bistro, a French bistro, café, and bakery centrally located between Chatham and Provincetown. Start with the steamed beet salad with goat cheese and candied walnuts, then sample the artichoke heart stuffed with clams and the wasabi-crusted yellowfin tuna. For cocktails, consider Aqua Bar, a casual beach bar with live music.
Check out farm-to-table restaurant Spoon and Seed for breakfast or an early brunch in Chatham. Order the organic maple-cinnamon farro and quinoa porridge topped with fresh berries or a veggie bowl with eggs, avocado, roasted seasonal vegetables, quinoa, and chia seeds.
Refuel after an active morning at the family-run Public Café. Try the turkey pesto sandwich on multigrain, topped with a sunflower seed pesto, cheddar, tomato, and onion or the gluten-free chicken and vegetable curry.
Take in the sunset and a cocktail at The Veranda. Let one of their experts mix you a drink as you look out over Pleasant Bay. For dinner, sit outside at The Wild Goose Tavern in the heart of Chatham Village. Bid goodbye to the Cape with a locally-sourced seafood meal of dishes like Chatham mussels in garlic, shallots, and white wine sauce, blackened fish tacos made from the daily catch, or baked Atlantic cod with lemon-herb gremolata.