Provincetown
The most atmospheric tip of the Cape, but you pay for it
Provincetown sits at the very tip of Cape Cod, 120 miles from Boston and about as far from ordinary as you can get on the East Coast. Commercial Street is the artery: galleries, drag shows, fried clam shacks, and a harbor with fishing boats all within a 10-minute walk. The East End is quieter and more residential. The West End has most of the nightlife. Race Point Beach and Herring Cove Beach, both part of Cape Cod National Seashore, are 3 miles from Commercial Street by bike or shuttle. Bradford Street runs parallel to Commercial and is where you find the more affordable guesthouses. The Pilgrim Monument towers over everything at 252 feet and is climbable in about 20 minutes. MacMillan Wharf has ferry service to Boston in summer. Parking is brutal from late June through August. Come without a car if you can.
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