Provincetown, Massachusetts Weekend Guide: Best Hotels, Restaurants, and Things to Do

Decades ago there was a sign at the branch of Routes 6 and 6A leading into Provincetown, MA, the onetime Portuguese fishing village located at the very tip of Cape Cod that read, “Provincetown Either Way.”

The sign offered direction, but it was also a metaphor for the open-minded attitude of this tiny town (just 17.5 square miles, almost half of it water), which, even today, is a haven for tourists and townies, weekenders and full-timers, gays and straights, singles and couples, families and friends.

For me, who spent all my childhood summers there and, as an adult, never miss spending a week or two there each year, it is a slice of heaven.

Growing up, my family rented a three-bedroom apartment known as “Garbage Gables” on the town’s main thoroughfare, Commercial Street, right on the bay. Its big, rickety, waterfront porch creaked and swayed dangerously in the wind. Legend had it that playwright Eugene O’Neill had stayed here, inscribing poetry on the ceiling beams.

My mom, an early hippie, worked at a leather shop, handcrafting sandals. My brothers and I roamed freely. As soon as we arrived from our Connecticut home, we would hightail it into town to one of several insanely overstocked penny candy shops (some still exist) and load round wicker baskets with sweets. After swimming in the bay all day we would pluck snails and mussels off rocks, dig for clams, and steam them for supper, melted butter running down our chins.

Today, an official clamming license is a must, and our ramshackle abode has long been converted to chic condos that sell for around a million bucks. But though the town has changed, it still seeps into your soul like magic — the extraordinary light, views, dunes, and colors are inspirational. There’s food that can sate any palate, and plenty to do whether you’re all about the outdoors or a shopping and dining sophisticate.

One thing has remained constant: Provincetown’s embrace. You’ll want to stay longer, but if you only have three days, here's how to make the most of your time.

How to Get to Provincetown

You can come by plane, boat, and automobile, the latter great for getting around, though parking is difficult in town. In high season, the one way in and out on Route 6 can be a traffic nightmare. There are regular Cape Air flights from Boston Logan and Provincetown Airport but better still, take the 90-minute ferry from Boston run by Bay State Cruise Company and Boston Harbor Cruises at the South Station. There are several sailings each day during the season. Book ahead, because they are b-u-s-y.

As for packing, keep it simple. It’s not the Hamptons. Provincetown (AKA PTown) daytime wear consists of shorts, bathing suits, sports gear, and flip-flops. Dressing up at night means putting on a pair of jeans and a clean shirt. (The exceptions are the female impersonators — you might run into Cher — who cruise Commercial Street in full drag, promoting various nighttime shows.)

Where to Stay in Provincetown

Assuming you take the ferry, you’ll be delivered into the town’s center, Macmillan Pier, the dividing line between the city’s East and West Ends. The Pier itself is lined with touristy stops — t-shirts, fudge and taffy makers, ice cream shops, fast food, and more. You’ll immediately get the artsy vibe of the town and an eyeful by making your way on Commercial Street, which is lined with great restaurants, art galleries, indie shops, and antique stores.

There are VRBOs, hotels, motels, and bed and breakfasts galore, many within walking distance of the pier. There are also plentiful taxis and pedi-cabs if you don’t want to schlep.

Set back off Commercial Street and about a five-minute shuffle from the pier is the lovely Pilgrim House, est. 1810, a totally renovated boutique hotel with three floors and 19 rooms. Henry David Thoreau was reportedly a guest. The place is immaculately clean but not frilly, offers a free continental breakfast, and has a restaurant and bar.

The Harbor Hotel on the East End is across the street from one of PTown’s most iconic bay views. There’s a pool and a toasty fire pit where guests hobnob and sip drinks from the in-house Whaler Lounge & Restaurant. Bonus: It’s extremely family- and pet-friendly, along with being well-priced.

Much fancier, but still oozing with the authentic flavor of the town is the The Red Inn, small but luxurious, built in 1805, last renovated in 2011 and set smack on the bay in the West End, it offers beautifully appointed guest quarters with gorgeous views, fireplaces, beamed ceilings, and wide-plank floors. Reserve early. If you don’t want to splurge, come for a drink and apps at what might be the most convivial bar in town.

Day One

If it’s already afternoon, and you’re hungry — but not yet for dinner — make your way to Mac’s Fish House for happy hour starting at 4 p.m. Slurp down the freshest, briniest oysters until you burst for $1 each. Mac’s also serves the most divine New England clam chowder that happens to be gluten-free.

You’re recharged, so check out the famous Boatslip Tea Dance on the West End for some serious cardio. It’s a wild dance-a-thon that caters the to the LGBTQ+ community (but everyone's welcome!) and runs daily in season from 4-7 p.m. If you don't feel like working up a sweat, head to the Far Land On The Beach concession at beautiful Herring Cove Beach where there’s a DJ spinning mellow tunes. Catch sunset, chow down a luscious lobster roll, and wash it down with wine or beer. (On Wednesdays and Sundays there’s live music, too.) Most Friday nights, the National Park Service lights a bonfire to enhance the mood.

Then it’s back to town, to take an introductory stroll on open late Commercial Street. Artists have flocked here for more than a century and galleries often have openings on Friday nights when gallery hopping is, well, high art. A favorite of mine is Kiley Court where artist Robert Cardinal captures the essence of the Cape in oil. Recently, his son Julian has garnered attention for his fashion paintings.

You’re tuckered out but still a bit hungry and don’t want to fuss? Tuck down an alley near the Pier and grab a takeout order of outrageously delicious, authentic, handmade dumplings at Kung Fu Dumplings. Sit, eat, and people watch on a bench at Town Hall.

Day Two

Rise early and grab an egg sandwich with linguicia, the spicy Portuguese sausage, at the iconic Portuguese Bakery. Breads and pastries are fresh and fabulous. Succumb to Malassada (sweet fried dough).

Right off, you’ve blown your diet, but you can assuage your guilt and cover some ground by renting a bicycle for the day at one of many local bike shops, including Provincetown Bike Rentals, Gale Force Bikes, and the Bike Shack.

It’s fun and easy to ride through town, but sometimes crowds make it tough to maneuver. Consider a just-challenging-enough pedal on the Provincelands Bike Trail, a five-plus mile loop that takes you through dunes, pine forests, and cranberry bogs. Add a few miles with extensions to Herring Cove Beach, Race Point Beach, and Bennett Pond. You can enter and exit at various points.

With guilt in your rearview mirror, grab lunch at one of two beloved takeouts: Pop + Dutch, the sandwich shop and pint-sized specialty grocery store run by two Brooklyn expats known for their lovingly layered sandwiches, or Relish bakery & sandwich shop, where the sandwiches are good and the cupcakes draw crowds.

Attention shoppers: Now’s a good time to check out a slew of quirky-cool stores. Visit Yates & Kennedy chockfull of interesting and stylish found objects, original hand-screened t-shirts, beautiful frames, vintage and leather goods, jewelry, and enchanting stuff for the home.

Also thoroughly enchanting is The Captain’s Daughters, an airy, sunlit space which bills itself as a purveyor of “seaside sundries and tea bar” where you’ll find “elevated” souvenirs and accessories, wellness offerings (there’s a plentiful collection of topical CBD creams), and a massive selection of specialty teas (you can also get a cup at the café here).

The John Derian shop is set in an old sea captain’s house, just a hop off Commercial on Law Street. You’ll discover a trove of artist Derian’s famously graphic decoupage pieces, along with plenty of other home goods. There’s Loveland, a fabulous and slightly kitschy shop featuring the works of local artists and craftspeople. It’s brimming with delightfully odd knick-knacks, home goods, and gifts.

Finally, a must stop is Marine Specialties, where the inventory is positively cuckoo, ranging from coffee mugs to military and faux-military outfits. We’ve even spotted a gas mask here.

Not a shopper? Sign up for the Herring Cove Tidal Lake kayak tour at Provincetown Aquasports. Plan this a day ahead. You can “ride the tide” in and out of peaceful tidal “rivers” during this two-hour guided tour. It doesn’t require experience and launches at The Moors at the end of Route 6.

Make a reservation in advance for The Mews Restaurant and Café. It’s one of the few upscale restaurants that is open year-round. Try to reserve a table by the window. With a gorgeous view of the bay and little tea lights sparkling overhead, it’s romantic, without feeling like Valentine’s Day. The food is mostly American with a touch of the exotic and ranges from juicy Angus burgers and big steaks to Indian-inspired lobster Vindaloo. Do consider a specialty martini… there are more than 300 vodkas on the menu.

If you’re with a group check out Spindler’s, where there are delicious “crafted” cocktails and wooden serving boards laden with everything from smoked and cured fish to charcuterie and cheese. These are crowd pleasers. (Note to bread lovers: try Spindler’s homemade “charred” bread with honeyed butter. It’s worth it.) Flip side, if you’re looking for a serene dining scene in an uber-charming setting consider Mistralino on Bradford. Under newish ownership they turn out perfectly prepared Italian classics such as chicken parmesan or more sophisticated dishes such as spring pea agnolotti.

Sated, go to a show. Get ready to bust a gut at Dina Martina, the wildly popular, profoundly irreverent drag goddess who spends the summer in PTown performing at the Crown & Anchor. There are loads of other shows as well. Check out the schedule at the Art House for acts ranging from musical to comedy, along with visits by Debra Messing and Kathy Najimy this summer. In the mood for a spirited sing-a-long? On Friday and Saturday gather ‘round Bobby Wetherbee’s piano at the Dive Bar at the Crown and Anchor and belt out popular tunes. Wetherbee has been gigging there for 50 years and is a legend.

Day Three

Admit it, you’re zonked. Maybe a little hungover. Play through the pain. Have a big breakfast/brunch at Chach where the diner-like exterior belies the luscious menu including homemade muffins, overstuffed breakfast burritos, and all kinds of yummy Benedicts. Another great choice is the homey Liz’s Café, Anybody’s Bar where you must try the flippers (a Portuguese favorite): fried dough, Vermont syrup, sweet butter, and powdered sugar. Soak up sins of the night before with the homemade corned beef hash or maybe it’s the hair of the dog that bit you. Try a great Bloody Mary here.

After a big breakfast, it’s probably a good time to climb the Pilgrim Monument, a 252-foot tower in the center of town with 116 steps. It was built in 1907 to commemorate the 1692 arrival of the Mayflower here, the Pilgrims’ first landing in the New World in Provincetown. The breathtaking view at the top encompasses most of the town.

If you really want to pack it in a memorable finale to your visit, consider a whale watch at Dolphin Fleet Whale Watch (lucky passengers on these three-to-four-hour trips will see a variety of whale species, including a Humpback that is sometimes spotted with a newborn calf). Alternatively, you can get a gander at seals, whose population is growing, on the Provincetown Seal Tours. This outfit runs 45-minute tours six times a day.

You’ll feel like you’re on another planet on a guided tour of the Provincetown dunes, part of the Cape Cod National Seashore. An accurate use of the word awesome, some of the dunes are 100-feet tall. You can get a glimpse of the legendary dune shacks, where artists and writers still go for solitude and inspiration, and where the likes of Jack Kerouac and Tennessee Williams have labored. Five times a day, Art’s Dune Tours takes visitors out for one-hour tours.

And, ahoy, Mateys, if you happen to have a thing for pirates, check out the Expedition Whydah Pirate Museum on your way out of MacMillan Pier. There, you’ll find artifacts and treasures recovered from the only authenticated pirate ship wrecked in the area — this one in 1717 off Wellfleet, two towns from PTown.

Don’t leave before grabbing a kale soup at the Lobster Pot restaurant at the Pier. The hearty meal in a bowl was a staple for Portuguese fishermen and is popular today. It’s loaded with linguica, kidney beans, potatoes, onion, and of course kale. (My mom made a great one.)

First-timers to Provincetown should consult the always helpful Provincetown Chamber of Commerce posting a calendar of events including festivals, parties, and theme weeks, and offering help with last-minute lodging suggestions for spur-of-the-moment visitors.

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