Three Days in Provincetown—What to See and Do

If you’re looking for a quick summer vacation, head to Provincetown (better known as P-town), the former Portuguese fishing village that T+L readers have named America’s favorite beach town. Visitors to P-town return for its quirky small-town character, stunning seashores, and the salt-scented air that is quintessential New England.

Getting to P-town is easy, since you can arrive by boat, car, or plane. Cape Air has multiple flights every day between Boston Logan and the Provincetown Airport, where you can get a taxi to your hotel. If you’re flying into Boston and plan to take the ferry, give yourself at least an hour between wheels down and your ferry departure time. Alternatively, if you’re traveling into Boston by rail, Amtrak trains bring passengers to South Station, which is a 20-minute walk or short cab ride to the ferry docks. The high-speed catamarans run by Bay State Cruise Company and Boston Harbor Cruises have multiple boats per day, but check their schedules and book ahead of time—otherwise you might miss the last ferry and get stuck in Boston overnight. If you’re planning to drive the length of the Cape along U.S. Highway 6, be aware that weekends during the high season are usually fraught with traffic and delays. Parking in Provincetown is also an issue, so traveling without a car is preferable.

Day One

If you’re arriving in the afternoon by ferry, most hotels, bed-and-breakfasts, and Airbnb and vacation rentals are located within walking distance of MacMillan Pier, which divides the city into the East and West Ends. A walk down Commercial Street, Provincetown’s main thoroughfare, will give you a quick introduction to the city’s artistic atmosphere and friendly year-round locals and seasonal residents, who are affectionately referred to as "townies." Commercial Street is lined with art galleries, boutiques, antiques shops, and many great restaurants. Our preferred hotel option is the Salt House Inn.

After you’ve checked in to your accommodations, pick up a bicycle rental. This is the best mode of transportation in the city and will give you the most freedom. We recommend Ptown Bikes, Gale Force Bikes, and the Bike Shack. Reserve your rental at least a week ahead of your trip, especially during high season. Prices start at $23 per day, but you can also rent by the hour.

During the summer season, don’t miss the Tea Dance at the Boatslip Beach Club from 4 to 7 p.m (admission is $5). The popular daily LGBT (but very hetero-friendly) social event is a great place to sip cocktails, show off your dance moves, and make new friends. Even if you’re not up for twirling to disco beats, the Tea Dance is always great for people-watching.

If a late-afternoon dance party isn’t your thing, check out JD’s, a sports bar with a second floor terrace. The daily happy hour from 4 to 6 p.m. has cheap local oysters, crab claws, and $5 sushi rolls.

One of the best new restaurants to open in Provincetown in recent years, Canteen has the best lobster roll on Cape Cod. Order it hot or cold—either way is perfect. The fish-and-chips and cod bánh mì are also delicious. Place your order at the counter, then find a table in the backyard, which has sublime views of Provincetown Harbor.

If art is your thing, take an evening constitutional for the Friday night Gallery Walk, when the city’s dozens of art galleries stay open late. Most of the galleries are in the East End, so start there and head west.

Day Two

Joe’s Coffee & Café and Kohi are both locally owned options for strong coffee and a quick breakfast to fuel the day ahead. If you’re looking for a sit-down option, check out Café Heaven for standard brunch fare.

Between April and October, the waters off of Cape Cod are perfect for spotting humpback whales. Book ahead for an early-morning sightseeing cruise with Whale Watch Dolphin Fleet, which has multiple departures from MacMillan Pier throughout the day.

Back in port, hop on your bike and head west. Stop in at general store Pop + Dutch to order sandwiches (we love the Carolina Gentleman, with spicy pimento cheese) and stock up on snacks and drinks for a beach picnic before biking to Herring Cove Beach.

To get to the beach, continue west on Commercial Street and take it as far as possible, following the road as it winds north at the Pilgrim's First Landing Park. Head out of town and toward the salt marshes, which will be on your left. After a half-mile, you'll spot a large wooden bicycle rack located just outside of town on Route 6A. Lock up your bike and follow the trail to the beach. From here, it’s a 15-minute schlep to the shore. Depending on the tides and time of day, be prepared to wade through the tidal pools and salt marshes. The path is unmarked, but fairly easy to follow—just look for the footprints. While it’s not officially a nude beach, the farther you walk along the shore, the less clothing you’ll see. On the way back, you can walk across the moors and swim in the tidal pools if the tide is in.

If you have a car, you won't be able to park along the road, but you can drive further down Route 6A to get to the Herring Cove Beach parking lot, where you’ll pay $20 to park within the U.S. National Seashore.

After an afternoon of sand and sun, head to your hotel to refresh before enjoying sunset cocktails and dinner at the historic Red Inn, located in a former home built in 1805. Captain William Bradford purportedly stepped off the Mayflower and first set foot on the beach here in 1620. Try anything from the raw bar or the local seafood dishes from executive chef Philip Mossy.

If you’re not too tired, cap off the evening with a drag show. America's still-undiscovered national treasure, Seattle-based Dina Martina, spends summers in P-town performing song-laden comic masterpieces. She’s an American Miss Malaprop and is not to be missed. If the show is sold out, go see any of the other performers at the Crown & Anchor, or entertain yourself with a sing-along or open mike at the hotel's piano bar or at the nearby Tin Pan Alley.

Toward the end of the night, everyone in town inevitably ends up at the Atlantic House, the oldest gay nightclub in the U.S.

Day Three

If you have the stamina after a late night on the town, climb the ramps and steps to get to the top of the 252-foot-tall Pilgrim Monument, which dominates the Provincetown landscape and was erected in 1910 to commemorate the arrival of the Pilgrims. From the top, you’ll get a bird’s-eye view of the city and harbor.

Jump back on your bike and head to Race Point for a long ride along the twisty paved Province Lands Bicycle Trail, maintained by the National Park Service. The best time to bike through the dunes is late afternoon, when the sunlight turns the sand orange and pink. For some true peace and quiet, you can also stay overnight at the Race Point Lighthouse keeper’s cottage. Park your bike near the lighthouse and hike to the dune shacks, which have housed writers- and artists-in-residence since the 1920s.

If you’re a lighthouse junkie, there are two others to see in Provincetown. Back in town, walk the harbor break wall from Pilgrim’s First Landing Park out to Long Point Beach, where you can spot both of them: Long Point Light and Wood End Light. Great photo ops abound, but give yourself enough time to walk back. A round-trip hike to the end of Long Point should take three hours.

If shopping is more to your nature, you have many options for gifts, antiques, and one-of-a-kind souvenirs. For the best local T-shirts, go to Tim Scapes for designs with a modern twist or Hook Provincetown, located in a teensy narrow storefront. The Provincetown Bookshop has a broad assortment of classic lit, summer beach reads, and a good selection of Cape Cod authors. Stop in at Loveland in the West End for bohemian marine-themed home décor and gift items. For antiques, go to Remembrances of Things Past, Yesterday’s Treasures, and Scott Dinsmore. Don't miss Marine Specialties for an oddball assortment of quirky gifts and ocean relics.

If you have time for one last meal before boarding the ferry back to Boston, stop in at the Lobster Pot for Portuguese kale soup and a lobster combo meal. The restaurant's famous neon sign is a beacon for seafood lovers.

Staying a third night? Take a twilight sail on a chartered schooner. A two-hour tour on the Hindu, a Provincetown fixture since 1946, will give you gorgeous views of the harbor, town, and beaches. Bring a bottle of wine and snacks for a romantic sunset cruise.

First-time visitors to Provincetown should check the Provincetown Chamber of Commerce’s calendar of events to see if your trip coincides with any of the popular theme weeks. This diverse city is a year-round destination for the LGBT community, and the summer season is filled with many parties and festivals. The Chamber also maintains a very helpful list of properties that have last-minute availability, since summer weekends get booked far in advance and tend to have scant vacancy.

Christopher Tkaczyk is the Senior News Editor for Travel + Leisure. Follow him on Twitter and Instagram at @ctkaczyk.

For more long-weekend itineraries in America's best vacation destinations, click here.