How to See Provincetown as a One-Day Side Trip from Boston

Windswept sand dunes and a windswept Cher impersonator riding a stand-up scooter down Commercial Street—those are basically the two poles of any getaway in Provincetown, Massachusetts.

I saw both during a recent summer day trip to the artsy, historic, and extremely LGBTQ+-friendly seaside charmer on the tip of Cape Cod. 

My mission was to get as much of the P-town experience as possible without staying overnight, toggling between the destination’s two sides—the natural and the sociable. Follow in my sandy footsteps and you won't hit every Provincetown highlight, but you will come away with a good understanding of what makes the place special. 

The most feasible option for going from the Boston area (where I live, and where I’m basing you on this hypothetical New England vacation of yours) to Provincetown and back in a single day is the Fast Ferry operated by Bay State Cruise Company or Boston Harbor Cruises’ Provincetown Ferry. 

From spring through early fall, the ferries run between the Boston waterfront and P-town several times a day, 7 days a week. (Note that the itinerary that follows is likewise good for spring, summer, and early fall; options on Cape Cod grow limited in winter.)

Don’t try to drive all the way to Provincetown and think you can get a full day of activities in before returning to Boston by nightfall. Summer traffic is notoriously slow and parking in P-town is scarce. You won't need a car once you get there, either—everything is within easy walking or biking distance. 

For my August day trip, my husband and I caught the first Fast Ferry of the day, which pulls out of Boston’s Seaport District at 8:30am and arrives at Provincetown’s MacMillan Pier a mere 90 minutes later. Book the last returning ferry, departing Provincetown at 7:30pm, and that gives you more than 9 hours to fill on the Outer Cape.

Walking straight ahead from the marina, the first thoroughfare you’ll come to is Commercial Street. It’s the town’s, well, commercial street. 

In many ways, P-town’s lively waterfront—with its seafood restaurants, cute shops, and smattering of shingled homes—resembles many other New England coastal villages that have turned their focus from hooking fish to hooking tourists. In Provincetown, though, you’ll see quite a bit more rainbow flags and flyers for drag shows fluttering in the breeze.

No one I spoke with could pinpoint why, exactly, Provincetown became such a gay haven, though wall text at an exhibit at the Provincetown Museum theorizes that the thriving LGBTQ+ presence could be a result of Provincetown’s popularity with early 20th-century bohemians (especially theater artists and painters) or the welcoming attitudes of the Portuguese immigrants who settled here to work in the fishing industry. 

Speaking of that Iberian heritage, Commercial Street’s historic Portuguese Bakery (299 Commercial St.) deserves a stop whether you’ve had breakfast yet or not. Try the custard cups known as pastéis de nata (pictured above) or the clumps of cinnamon- and sugar-dusted fried dough called malasadas.

For a quick, scenic survey of the natural setting, take a 1-hour sightseeing excursion in an SUV from Art’s Dune Tours (4 Standish St.), whose guides have been schlepping tourists through a portion of the Cape Cod National Seashore since 1946 (though the coast wasn’t designated as such until 1961).

Art’s son, Rob Costa, now runs the business. If you ask nicely, maybe he’ll play for you his carefully preserved answering machine recording from foghorn-voiced movie star Kathleen Turner, calling to inquire about whether her own dunes tour will proceed despite a rainy forecast (“Will you go OUT?” she booms, sounding like Lady Macbeth on a beach vacay). 

Out on the dunes, it’s easy to see why painters like this place. Next to the glimmering Atlantic and under a kind of creamy light, ever-shifting sandy hills sport a patchy array of scrub oak, scraggly grasses, beach plums, and rose hips. According to Costa, this vast protected expanse makes up well over half of Provincetown’s land area. It's devoid of human dwellings save for 19 historic shacks, nine of which are owned by nonprofits that use the buildings as temporary residences for artists and writers looking to work without pesky distractions such as indoor plumbing. 

Back in town, you can have a lobster roll for lunch at the popular and photogenic Lobster Pot (321 Commercial St.) if you want. But if, like me, you’re a vegetarian, I recommend the hearty and tangy Mediterranean grain bowl at Provincetown Brewing Co. (141 Bradford St.), which is also home to several sassily named beers and a Dolly Parton pinball machine I coveted intensely.

From Bradford Street, ride the recently installed inclined elevator to the top of High Pole Hill Road, site of the imposing Pilgrim Monument, a 252-foot-tall granite tower completed in 1910 to commemorate the 1620 landing of the Mayflower Pilgrims, who spent about 5 weeks in Provincetown before making a more permanent settlement in Plymouth. (P-town’s soil was too sandy for crops.)

The climb to the top of the monument involves 116 stairsteps and 60 ramps. About 350 feet above sea level, the view from the summit takes in the harbor, distant lighthouses, and, if the skies are crystal-clear, the Boston skyline 42 miles away.

Back at ground level, the adjacent Provincetown Museum walks you through four centuries of P-town history, with artifacts such as huge whalebones and playbills from early Eugene O’Neill premieres. Two new and long overdue exhibits chronicle, first, the Mayflower landing from the perspective of the Indigenous Wampanoag people, and, second, first-person narratives from members of the town’s LGBTQ+ community. 

From here, you can either take a leisurely stroll to peruse the galleries and boutiques on Commercial Street’s East End, or, if you didn’t use up all your energy climbing the monument, rent a bike and hit the Province Lands Bike Trail to loop through pine forests, go past cranberry bogs, and reach beaches such as Herring Cove and Race Point (there’s also a public shuttle to the sand).

My spouse and I went the bike route, borrowing wheels from Provincetown Bike Rentals (136 Bradford St.) and winding up at Boy Beach (just south of Herring Cove), where the crowd is predominantly queer and the swimsuits skimpy—or, in some cases, nonexistent, seeing as how the unofficial dress code is clothing-optional.

Reader, I opted for clothes.

Our schedule didn’t afford enough time to work up the necessary nerve to go au naturel anyway. After a dip in the sea and a brief spell in the sun, we were back on our bikes and pedaling to town.

[Related: Nude Beach Etiquette: 7 Rules for First-Timers]

With bikes returned and the ferry’s departure time still an hour or so away, you can wait with a drink at one of the town’s bars to sample the nightlife you’ll be missing after you leave around dusk. We had beers at the Atlantic House (6 Masonic Place), which purports to have been in continuous operation for more than two centuries.

Or, if you finish your sightseeing by 4pm, you can take part in Boatslip Resort’s Tea Dance (pictured above; 161 Commercial St.), a sweaty, queer-oriented, 3-hour outdoor dance party that’s held every day during summer. 

Just don’t drink so many rum punches that you miss your boat back to Boston.