Published: June, 2020
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Provincetown (Ptown), Massachusetts

“It is the Morocco of America, the New Orleans of the north.” ― Michael Cunningham, Land's End: A Walk in Provincetown
— Rachel Wynne
  • More about your oliver guide:
  • Trip type: Adult, Beach
  • Activity level: moderate
  • Ideal length of trip: Long weekend

to & from

During the summer 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.

Where to Stay

There are dozens of amazing small boutique hotels tucked away in Provincetown. I suggest checking out the location before booking- in town vs out of town. If you want quiet retreat do not stay in the heart of town.

Where to Eat and Drink

Restaurants come and go in Ptown. From fish shacks to high end dining, Ptown offers something for everyone.

  • I like walking out to the West End in the morning and popping into small bakeries ( and boutique food markets for morning tea and pastries. Reservations are encouraged for the nicer spots in town.
  • Joon Bar: We have had some nice meals at the bar. Local seasonal specials.
  • Red Inn: Classic Cape Cod dining with a great view.
  • Ciro and Sals: A Ptown classic, italian fare.
  • Provincetown Brewing Co: Opened recently, casual off Commercial Street.
  • Lobster Pot: What you see is what you get- if you want a lobster roll this is your spot.
  • Mac’s Ptown: On the outskirts of town, Mac’s has become the defacto seafood spot on the Cape. Always consistently good. We like the sushi the best! And stop by their fish market next door for the local catch and great sauces as well as take away.

What to Do

Strolling Commercial Street is an activity unto itself. I prefer the outskirts of town. I particularly like walking in the West End where beautiful seaside homes are perched on the edge of the sea. The nightlife in Ptown is definitely geared towards the LGBTQ+ but can be enjoyed by all. There is never a lack of things to do in Ptown.

  • Galleries:A few galleries not to miss: Berta Walker Gallery 208 Bradford Street, Four Eleven Gallery 411 Commercial Street, Provincetown Art Association and Museum (PAAM) 460 Commercial Street (great seasonally curated shows and also week long workshops)
  • Climb Pilgrims Monument: 252-foot tower in the center of town with 116 steps built in 1907 to commemorate the 1692 arrival of the Mayflower. The Pilgrims’ first landing in the New World in Provincetown
  • Whale Watch: Dolphin Fleet
  • Sunset cruise: Bay Lady II or Hindu 
  • Bike: The Provincelands Bike Trail, a five-plus mile loop that takes you through forests, dunes and bogs. There are plenty of bike rental places in town.
  • Herring Cove for sunset Pack a picnic from FarLand Provisions 150 Bradford Street Small corner store & deli featuring on-site bakery and prepared foods
  • Take a Dune Tour: Art’s Dune Tours provides a off-road tour experience to our family of visitors through the heart of the National Historic District of the Cape Cod National Seashore Park.
  • Shopping: The Provincetown Bookshop 246 Commercial Street , Marine Specialities 235 Commercial Street, Shor Home 240 Commercial Street, Captain’s Daughter 384 Commercial Street, Century 191 Commercial Street
  • Dance!: 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.

inside scoop

Ptown is crowded, really crowded in the summer months. Go in September or October when the crowds die down and it is easier to navigate. If you are there in the summer months stay in the West End.

skip it

Skip huge festival weekends. It is just mayhem (unless mayhem is what you are looking for).

What to Pack

Anything goes in Ptown! We have seen it all from leather chaps to drag to speedos. We have also seen impeccably dressed men out on the town. It all depends on what you are there for. Casual day wear more dressed in the evenings.


From lobster rolls to drag queens there is a little (or a lot) of something for everyone in Provincetown, MA. My childhood summers were spent one town over, when Provincetown was an art mecca and a somewhat sleepy Portuguese fishing town. Now there is nothing sleepy about Provincetown (unless you are there in December). Provincetown has become a summer gathering place for the LGBTQ+ community and it feels like celebration on Commercial Street everyday.

Still grounded in the arts- From the 1940s to the 1950s, Provincetown was a summer center of Abstract Expressionism represented by such painters as Franz Kline, Jackson Pollock, Lee Krasner, Motherwell, Helen Frankenthaler and Fritz Bultman, in addition to Hofmann. And more recently Mary Oliver, Joel Myerowitz, Michael Cunningham and John Waters (who I have been seated next to on Cape Air 8 seater flights) Provincetown is an eclectic mix of communities gathered on a small sand bar on the tip of Cape Cod.

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