9 a.m. Dig into diner classics
Comfort food is the specialty at Chach, located just northwest of the town’s center. A classic diner vibe is in full effect here, and tables of close friends pick up on the previous day’s conversations without missing a beat. Fuel yourself with vanilla-infused French toast topped with fresh fruit ($15) or eggs Benedict with applewood-smoked bacon, tomato and avocado ($17). You’ll find that same inviting atmosphere — and more brunch favorites — at the West End’s Liz’s Cafe, Anybody’s Bar, which also offers outdoor dining. Go for the chicken and waffles ($15) and order a plate of Portuguese flippers — sugar-dusted hole-less doughnuts ($11) — for the group.
10 a.m. Explore the dunes
Provincetown’s dunes occupy a prominent position within local lore; as the philosopher Henry David Thoreau wrote of them in 1865, one can look out “and put all America behind him.” Now part of the federally protected Cape Cod National Seashore, the dunes stretch out behind the length of the town like an unspoiled and uninhabited sandy backyard — with the exception of 19 shacks originally built for ocean rescuers that became off-the-grid getaways for writers and artists including Jack Kerouac and Jackson Pollock. The National Park Service provides free ranger-led walks into the dunes. Experienced hikers can explore on their own by following the Dune Shacks Trail for about two miles north from where Snail Road meets Route 6. For a less strenuous hourlong journey, hop into one of Art’s Dune Tours’ S.U.V.s ($41), driven by guides well versed in the terrain and its tales.
1:30 p.m. Picnic on the beach
Since you’re now a bit sweaty, return to the center of town to pick up sandwiches and drinks at Far Land Provisions or Pop+Dutch and then head to one of Provincetown’s two marquee beaches ($15 per entry on foot or bicycle, or $25 per car, during the summer). Herring Cove Beach is a bit more social, with a snack bar, a summer concert series, and separate areas favored by gay men, lesbians and those who prefer to sunbathe au naturel. Race Point Beach offers bigger waves, as well as more striking visuals with steep dunes behind you and the expanse of the Atlantic stretching out endlessly ahead. It’s also frequently a lounging area for a horde of seals — as well as the great white sharks that cruise the shoreline to feast on them. Keep your distance.
4:30 p.m. Shop Commercial Street
Provincetown’s legal ban on national chain stores isn’t airtight, but it has helped usher in an array of quirky shops that line Commercial Street in the heart of town. Book lovers have several winning options, including Womencrafts’ unabashedly feminist-themed stock (look for its “48 Years Grateful for My Abortion” street sign), East End Books’ carefully curated new titles, and Tim’s Used Books’ selection of Cape authors and out-of-print art catalogs. Yesterday’s Treasures is packed with all manner of town ephemera, vintage postcards and unique gifts (a copy of “The Ethel Merman Disco Album,” anyone?). Mauclère Leather features handcrafted belts, bags and sandals; the Old Baby offers locally themed clothing with a wry edge; Respoke repurposes haute couture into no-less-haute hats and footwear (its motto, “I once was an Hermès scarf,” says it all).
8 p.m. Grab a lobster roll
Stay on Commercial Street for dinner in an invitingly casual setting at the Irish-pub-style Squealing Pig, where you can order the lightly battered fish and chips ($23) and pair it with a glass of Guinness stout ($9). The Nepali chicken curry ($19) is a less obvious, but no less savory, option (thanks to its Nepal-born chef). Or grab a seat in the Canteen’s backyard, where the beach party atmosphere draws a lively cross section of Provincetown — townie and tourist, young and old, gay and straight alike. Start with the crispy brussels sprouts ($10) and then settle in for a classic New England lobster roll ($28). The outdoor bar makes it easy to linger over drinks and bask in the harbor view as the sun sets behind you.
10 p.m.. Take in a drag show
Thespians love to cite Provincetown’s role as the birthplace of modern American theater thanks to the playwright Eugene O’Neill’s legendary productions here in 1916. (The cultural buzz from those stagings followed him back to New York, where he soon went from unemployable to Pulitzer Prize winning.) Such emotionally wrenching plays are a bit thin on the ground in Provincetown these days, but drama — at least in the form of over-the-top drag — is alive and well. There are plenty of performers paying dutiful tribute to divas past and present, but more interesting are the drag queens pointedly — and hilariously — taking aim at all manner of sacred cows, both gay and straight, in venues like the Art House and the sprawling Crown & Anchor complex (most tickets $35 to $45). You can’t go wrong with anything featuring Dina Martina, Varla Jean Merman or the Little Rascals-meet-Russ Meyer ensembles directed by Ryan Landry. (Needless to say, don’t bring the kids.)
1 a.m. Get in your last licks
Once the bars close at 1 a.m., Provincetown quickly goes dark. One of the few exceptions is Spiritus, started in 1971 by two visiting hippie entrepreneurs who were astonished to discover the town was without a single pizzeria. Over five decades later, Spiritus is still owned by the co-founder John Yingling, though you are more likely to find his grandchildren behind the counter, slinging pizza slices ($4) and scoops of locally made Lewis Brothers ice cream ($4.25) to hungry late-night revelers until 2 a.m. A fun crowd tends to gather out front in the wee hours, but the benches facing the street are prime people-watching real estate day or night.
