9 a.m.: Enjoy diner classics
Located northwest of the city center, Chach specializes in home cooking. In a classic diner setting, close friends sit at tables resuming conversations from the day before. Refuel with vanilla French toast topped with fresh fruit ($15) or eggs Benedict with applewood smoked bacon, tomato and avocado ($17). In the West End, Liz’s Cafe, Anybody’s Bar offers the same charming atmosphere and other brunch classics, and also offers outdoor dining. Order the chicken and waffles ($15) and bring your group for Portuguese flippers, sugar-dusted hole-less doughnuts ($11).
10am Exploring the sand dunes
Provincetown’s sand dunes hold a significant place in local lore. As philosopher Henry David Thoreau wrote in 1865, when you look out from the dunes, “all America is behind you.” Now part of the federally protected Cape Cod National Seashore, the dunes provide a pristine, uninhabited stretch of sand behind the town, like a backyard, except for 19 cabins originally built for ocean rescuers and which became an off-grid retreat for writers and artists such as Jack Kerouac and Jackson Pollock. The National Park Service offers free ranger-led dune walks. Experienced hikers can explore on their own by following the Dune Shacks Trail, about two miles north of where Snail Road intersects with Route 6. For a less tiring hour-long trip, hop in an SUV ($41) with Art’s Dune Tours, driven by a guide well versed in the terrain and its stories.
1:30pm Picnic on the beach
Working up a bit of a sweat, head back to the town center and grab a sandwich and drink at Far Land Provisions or Pop+Dutch before heading to one of Provincetown’s two famous beaches ($15 per person if you walk or bike, $25 per car during summer). Herring Cove Beach is a bit more social, with a snack bar, a summer concert series, and a separate area popular with gays, lesbians, and those looking to enjoy sunbathing in nature. Race Point Beach has bigger waves and more dramatic views, with steep sand dunes behind and the endless Atlantic Ocean ahead. It’s also often a place where seal colonies hang out, and great white sharks circle the shoreline to hunt them. Keep your distance.
4:30pm Shopping on Commercial Street
Provincetown’s legal ban on national chain stores isn’t total, but it has encouraged the emergence of a string of quirky shops along Commercial Street in the town’s center. Book lovers will find some appealing choices, including the explicitly feminist-themed goods at Womencrafts (look for the “Thank You for Abortion for 48 Years” sign), a selection of new releases at East End Books, and a selection of Cape authors and out-of-print art catalogs at Tim’s Used Books. Yesterday’s Treasures is full of all kinds of city ephemera, vintage postcards, and unique gifts (a copy of “The Ethel Merman Disco Album, anyone?). Mauclère Leather sells handcrafted belts, bags, and sandals. Old Baby offers locally-themed clothing with a wry edge. Respoke transforms haute couture into equally luxurious hats and shoes (the motto “I used to be an Hermes scarf” says it all).
8pm: Eat a lobster roll
Stay on Commercial Street for dinner at the Irish pub-style Squealing Pig, in a charming, casual setting. Order the lightly battered fish and chips ($23) and pair it with a glass of Guinness stout ($9). Try the Nepalese chicken curry ($19), a lesser-known but no less delicious dish (made by a Nepalese-born chef). Or take a seat in the back patio at the Canteen, where the beach party atmosphere draws Provincetown’s vibrant eclectic crowd (townsfolk and tourists, young and old, gay and straight). Start with crispy Brussels sprouts ($10), followed by a classic New England lobster roll ($28). Sit back and enjoy the harbor views as the sun sets behind you while you sip your drink at the outdoor bar.
10pm: Watch a drag show
Theater fans often cite Provincetown as the birthplace of modern American theater, with playwright Eugene O’Neill staging his legendary works here in 1916. (The cultural excitement from those productions continued after he returned to New York, where O’Neill quickly went from unemployed to Pulitzer Prize winner.) Though emotional theater is a little scarcer in Provincetown these days, drama, at least in the form of flamboyant drag, is alive and well. There are plenty of performers who pay faithful homage to divas past and present, but more interesting are the drag queens who openly and comically target all manner of sanctuaries, gay and straight, in venues like arthouses and the sprawling Crown & Anchor complex (most tickets cost $35 to $45). You can’t go wrong with any production featuring Dina Martina, Vera Jean Merman, or an ensemble that resembles director Ryan Landry’s Little Rascals-meets-Russ Meyer. (Needless to say, don’t bring children.)
1am, take that last sip
When the bars close at 1am, Provincetown gets dark quickly. One of the few exceptions is Spiritus, founded in 1971 by two hippie entrepreneurs who were surprised to find that there were no pizzerias in town. More than 50 years later, Spiritus is still owned by co-founder John Yingling, but you’re more likely to find his grandsons behind the counter, dishing out slices of pizza ($4) and locally made Lewis Brothers ice cream ($4.25) to hungry late-night revelers until 2am. A fun crowd congregates in front of the shop at dawn, but the street-front benches are great places for people-watching any time of the day or night.