1. Where to Stay
Watch the foot traffic along Commercial Street from the front-porch rockers at Anchor Inn Beach House (from $260), a 23-room mansion decked with ornate Victorian four-poster beds. Request one of the sixteen back rooms for a private balcony overlooking the boat-dotted bay.
Kick back in an Adirondack chair among wisteria and seagrass at the Inn at Cook Street’s garden (from $269; $185 after 9/7). The 1836 Greek Revival home is painted in warm pastels and adorned with gabled ceilings and patchwork quilts. (Pulitzer Prize winner Michael Cunningham wrote part of A Home at the End of the World from the second-floor Writer’s Room.) On weekend nights, guests can congregate around the open backyard grill.
Forgo typical B&B kitsch at the White Porch Inn (from $150), a nine-room estate favored for its whitewashed décor and proximity to Wired Puppy, a local gathering spot with the best coffee on the Cape, according to Cape Cod Life. Request the Long Point Light Room for sweeping views of the Harbor.
2. Where to Eat
Reserve a window-side table at the Red Inn, an upscale lodge with a huge brick fireplace and rustic wood detailing. Fresh seafood like oysters and cod are the specialties, all caught off the Cape Cod shores. Start with a pre-dinner tea-infused martini ($10) on the deck, where you can watch the evening sun glinting across the boats.
Assemble a picnic lunch at Far Land Provisions, a café and country grocery that sources its produce and meats from regional farms. Order the best-selling Pilgrim Lake sandwich—turkey, Cheddar, and cranberry mayo piled atop a bulky Portuguese roll ($6.50)—along with a homemade chocolate-chip cookie.
Feast on New England staples at the Mayflower Cafe, a local stalwart with vinyl booths, wagon-wheel lamps, and walls covered with caricatures from the forties and fifties. The spot is known for the best Cape-sourced lobster rolls in town: cut chunky and served on a buttered hot-dog bun with shredded lettuce ($13.95).
3. What to Do
Walk the fabled breakwater, a 1.2-mile wall of flat-topped rocks that connects the town to Long Point beach. Jump off on either side to swim to the private, islandlike sand dunes (around a fifth of a mile). Follow the worn-in sand path until you hit the beach, which is often deserted in early morning and late afternoon. Continue a mile down the surf to Long Point lighthouse, a deserted, beautiful structure that juts up just before the sand tapers into the sea.
Take a twenty-minute stroll across the dunescape toward Herring Cove Beach, a gathering spot for Provincetown’s sizable gay community (but welcoming to all). Lounge on the beach and wait for high tide, when the winding marsh paths you’ve just crossed will be flooded by water. Then grab a float and explore the blissfully quiet temporary riverways, shielded from view by high reeds. Bring goggles to watch the crabs scuttling underfoot.
Drive northwest to the end of the Herring Cove parking lots, then hang a right onto the windswept Hatches Harbor. The huge swath of sand turns into a sparkling, twelve-foot-deep pool during high tide, when local kids (and daring adults) cannonball into the water.
4. Insider’s Tip
Though the bars let out at the puritanically early hour of 1 a.m., don’t miss the after-party at Spiritus Pizza, the only eatery in town open until 2 a.m. The front patio becomes a nightly block party in summer, where regulars gorge on pizza and Emack & Bolio’s ice cream. The house specialty is the Greek slice ($3.75), topped with olives, onions, and feta cheese. Be aggressive when squeezing past the crush of revelers—orders are taken haphazardly at the counter.
5. Oddball Day
Before bumming around the beach, spend a day exploring town by bike. Start with coffee at one of two mainstays: On the East End, Wired Puppy’s medium-dark Sweet Puppy is the favorite; on the West End, Joe Coffee & Café’s (170 Commercial St.; 508-487-6656) blend hails from a Western Massachusetts beanery. Order breakfast at Cafe Heaven (199 Commercial St.; 508-487-9639), where local art covers the walls and the banana cornmeal pancakes are the specialty. Rent cycles at Ptown Bikes ($22/day) and hit the Province Lands Bike Trail, a hilly, five-mile loop that starts at Herring Cove Beach and winds through a picturesque dunescape. Follow the signs to Beech Forest, a prime destination for waterfowl watchers that runs alongside Bennett Pond, a freshwater pool awash in lily pads. Bike back along Commercial Street, stopping off at Marine Specialties, a massive curiosity shop crammed with everything from nautical kitsch to dead-stock vintage dishware. Afterward, spend the evening out on Commercial Street’s East End, where Norman Mailer lived for years. Dine at the bayside Mews Restaurant & Café, a romantic spot set back from foot traffic by lush topiary. Friday evenings mark the town’s official gallery crawl (7 to 9 p.m.), when residents stream down Commercial and free wine flows. Don’t miss landscape portraits by local painter John Dowd at William Scott Gallery and photographer Mischa Richter’s moody images of Provincetown people and places (August 27-October 24) at the Provincetown Art Association and Museum, open until 10 p.m. on Fridays (with free admission after 5 p.m.). Cap off the night at Enzo, a dimly lit basement bistro where native piano legend Billy Hough pounds out classic LPs like Ziggy Stardust from beginning to end (Fridays, 11 p.m.).
Provincetown.com is the go-to site for everything from inns to cabaret shows to galleries.
Wicked Local/Provincetown offers arts coverage of Provincetown and nearby Cape towns.
Watch the after-hours party form on the front patio of Spiritus Pizza from the spot’s webcam.