Explore Provincetown: A Guide for Your Visit
Back in the ’70s, 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 locals, weekenders and full-timers, gays and straights, singles and couples, families and friends.
For me, having spent all my childhood summers there and as an adult never missing a week or two visit each year, Provincetown 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 pick 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. However, 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 satisfy any palate, and plenty to do whether you’re into outdoor activities or prefer shopping and dining experiences.
One thing has remained constant: Provincetown’s welcoming 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 arrive by plane, boat, or automobile, the latter being great for getting around, though parking is challenging in town. In the 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 South Station. There are several sailings each day during the season. Be sure to plan ahead, as they tend to fill up quickly.
As for packing, keep it simple. It’s not the Hamptons. Provincial daytime wear consists of shorts, bathing suits, sports gear, and flip-flops. Dressing up at night typically 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 to the town’s center, MacMillan Pier, which divides 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 by making your way along Commercial Street, lined with excellent restaurants, art galleries, indie shops, and antique stores.
There are many vacation rentals, hotels, motels, and bed and breakfasts, many within walking distance of the pier. There are also plentiful taxis and pedi-cabs if you prefer not to walk.
Set back off Commercial Street, and about a five-minute walk 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 here. The place offers a free continental breakfast, has a restaurant and bar, and is immaculately clean but not overly fancy.
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 cozy fire pit where guests gather and sip drinks from the in-house Whaler Lounge & Restaurant. Bonus: It’s extremely family- and pet-friendly, along with being affordably priced.
Much fancier, but still infused with the authentic flavor of the town, is The Red Inn, small but luxurious, built in 1805 and last renovated in 2011. Set right on the bay in the West End, it offers beautifully appointed guest quarters with stunning views, fireplaces, beamed ceilings, and wide-plank floors. Reserve early as it can fill up quickly. If you prefer not to splurge, consider visiting for a drink and small bites at what might be the most convivial bar in town.
Day One
If it’s already afternoon and you’re hungry — but not quite ready for dinner — make your way to Mac’s Fish House for happy hour starting at 4 p.m. Enjoy the freshest, briniest oysters for just $1 each. Mac’s also serves the most delightful New England clam chowder, which happens to be gluten-free.
Once you’re recharged, check out the famous Boatslip Tea Dance on the West End for some serious cardio. It’s a lively dance-a-thon that caters to the LGBTQ+ community (but everyone is 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 a DJ spins mellow tunes. Catch the sunset, enjoy a delectable 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 atmosphere.
Then, it’s back to town for an introductory stroll along busy Commercial Street. Artists have flocked here for more than a century, and galleries often have openings on Friday nights when gallery hopping is quite the event. A favorite of mine is Kiley Court, where artist Robert Cardinal captures the essence of the Cape in oil. His son Julian has also garnered attention for his fashion paintings.
If you’re feeling a little tired but still hungry and don’t want to bother with dining in, head down an alley near the Pier for some 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 linguica, the spicy Portuguese sausage, at the iconic Portuguese Bakery. Their breads and pastries are fresh and fabulous. Don’t miss the Malasadas (sweet fried dough).
Right off, you’ve indulged but can balance it out 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 moderately challenging ride on the Province Lands Bike Trail, a five-plus mile loop that takes you through dunes, pine forests, and cranberry bogs. Extend your adventure with routes leading to Herring Cove Beach, Race Point Beach, and Bennett Pond. Entry and exit points abound.
Feeling good about your physical activity, grab lunch at one of two beloved take-out spots: Pop + Dutch, the sandwich shop and small specialty grocery run by two Brooklyn expatriates known for their expertly layered sandwiches, or Relish, where both the sandwiches and the cupcakes attract attention.
Attention shoppers: Now is the perfect time to explore quirky stores. Visit Yates & Kennedy, filled with interesting and stylish found objects, original hand-screened t-shirts, beautiful frames, vintage and leather goods, jewelry, and delightful home accents.
Another enchanting stop is The Captain’s Daughters, a bright, sunlit shop that offers “seaside sundries and tea bar” with a range of “elevated” souvenirs and accessories, wellness products, and an extensive selection of specialty teas (you can also enjoy a cup in their café).
The John Derian shop is located in an old sea captain’s house, just a short distance off Commercial on Law Street. You’ll discover a treasure trove of artist Derian’s graphic decoupage pieces alongside numerous other home goods. Don’t miss Loveland, a fantastic and slightly quirky shop showcasing local artists and craftspeople. It brims with delightful knick-knacks, home goods, and unique gifts.
A must-visit is Marine Specialties where the inventory is eccentric, featuring everything from coffee mugs to military-style outfits. You may even spot a gas mask.
If shopping isn’t for you, consider signing up for the Herring Cove Tidal Lake kayak tour at Coyote Kayaks. It’s advisable to plan this in advance. Enjoy a chance to “ride the tide” in and out of tranquil tidal “rivers” during this two-hour guided experience which requires no prior kayaking experience, launching from The Moors at the end of Route 6.
Make a reservation for The Mews Restaurant and Café which is one of the few upscale dining options open year-round. Try to reserve a table by the window for gorgeous bay views complemented by sparkling tea lights overhead, creating a romantic atmosphere without the stiffness of a formal dinner. The menu features everything from juicy Angus burgers and large steaks to Indian-inspired lobster Vindaloo. Do consider trying a specialty martini; they offer a selection of over 300 vodkas.
If you’re dining with a group, check out Spindler’s for expertly crafted cocktails and wooden serving boards piled with delicious options, from smoked and cured fish to charcuterie and cheese. Note: Be sure to try Spindler’s house-made “charred” bread accompanied by honeyed butter; it’s a must-have. Conversely, for a serene dining experience in a charming atmosphere, explore Mistralino on Bradford, known for perfectly executed Italian classics such as chicken parmesan or more sophisticated pasta dishes that evolve with the seasons.
Feeling sated, it’s time for some entertainment. Prepare for laughter at Dina Martina, the wildly popular drag performer who brings irreverent humor to her shows at the Crown & Anchor. There’s a variety of shows scheduled, so check out the program at the Art House for acts ranging from musical performances to comedy.
Day Three
By now, you might be feeling a bit fatigued, perhaps even slightly hangover. However, it’s time to persist. Enjoy a hearty breakfast/brunch at Chach, where the diner-like appearance hides a luscious menu that includes homemade muffins, overstuffed breakfast burritos, and a variety of Benedicts. Another great choice is the inviting Liz’s Café, Anybody’s Bar where you must try the flippers (a Portuguese favorite): fried dough, Vermont syrup, sweet butter, and powdered sugar. You can soak up the previous night’s indulgences with their homemade corned beef hash or perhaps embrace the “hair of the dog” with a great Bloody Mary.
After a substantial breakfast, it might be the perfect time to climb the Pilgrim Monument, a 252-foot tower located in the center of town with 116 steps. Erected in 1907 to commemorate the 1620 arrival of the Mayflower, marking the Pilgrims’ first landing in the New World, the breathtaking view from the top encompasses much of the town.
If you seek a memorable way to conclude your visit, consider a whale watching excursion with Dolphin Fleet Whale Watch. Luckier passengers on these three-to-four-hour trips might see a variety of whale species, including a Humpback frequently spotted with a newborn calf.
Experience the otherworldly beauty of the Provincetown dunes, part of the Cape Cod National Seashore. It’s among the few uses of the term awesome that truly apply; some dunes soar 100 feet tall. You may glimpse the legendary dune shacks, where artists and writers still seek solitude and inspiration, having once drawn in the likes of Jack Kerouac and Tennessee Williams. Five times a day, Art’s Dune Tours takes visitors on one-hour desert excursions.
Ahoy, mateys! If pirates pique your interest, check out the Expedition Whydah Pirate Museum on your way out of MacMillan Pier where artifacts and treasures from the only authenticated pirate shipwreck in the area—this one occurring in 1717 off Wellfleet, just two towns from PTown—await your discovery.
Before you leave, stop by the Lobster Pot restaurant at the Pier for a taste of Portuguese soup. This hearty kale-based dish, once a staple for Portuguese fishermen, remains widely popular today. It’s filled with linguica, kidney beans, potatoes, onion, and, of course, kale.
First-timers to Provincetown should consult the ever-resourceful Provincetown Chamber of Commerce, which posts a calendar of events including festivals, parties, and themed weeks, providing assistance with last-minute lodging suggestions for spontaneous visitors.
