Positioned at the very end of Cape Cod, Provincetown is a genuine outpost of welcome, and has been for centuries. The first landfall of England's Puritans, it grew as a fishing settlement, attracted artists with its renowned light, and now proudly proclaims itself a thriving destination for gay America.
What may be most remarkable about Provincetown, though, is what surrounds it—vast sand dunes and more than 30 miles of beaches that offer instant escape into seaside wilderness. Whether you're sunbathing on peaceful Herring Cove or walking into the breezes that cross Race Point Beach, the protection of the Cape Cod National Seashore designation keeps your views—and moments—pristine.
Downtown, the colorful historic buildings and friendly locals (including dogs, who seem to enjoy equal status with their masters) make every stroll here a rich event. Walking the length of Commercial Street, the town's main drag—from the gallery-lined East End to the rowdier, party-loving West End—lays out a lot of the enjoyment that Provincetown has to offer: everything from boutiques and bars to seafood shacks, fudge shops, bookstores, and coffee houses.
Where to Stay: Carpe Diem Guest House is an adults-only sanctuary a half block from the harbor. Its Namaste spa features a Turkish-style steam room and morning yoga. The breakfast here (included) is the best in town. Rates start at $199; 800-487-0132 or carpediemguesthouse.com.