Provincetown, Massachusetts
updated february 8 2024
The dunes at Race Point Beach
I only discovered the magic of Provincetown in June of 2009. I was going for what was intended to be a solo trip. As fate would have it, my then-new boyfriend ended up joining me at the last minute. Well, now he’s my husband and, needless to say, Provincetown is one of our favorite getaways. We’ve been going to P-Town every summer since (well, except for the infamous Covid summer of 2020). Magical light, lovely beaches, great restaurants, lots of tempting shopping (ask my husband), a vast selection of art galleries, and abundant (and varied) nightlife make Provincetown an irresistible summer destination (it can also be fun in off-season, too). While well-known as a popular LGBT destination, it is a welcoming a place for everyone to enjoy and for friends to gather.
From NYC, we typically take an early morning Amtrak train to South Station in Boston (4 hours). There we connect to the Bay State Cruises fast ferry (which takes 90 minutes), arriving in P-Town in mid-afternoon. Provincetown Cruises also offers a fast ferry from Boston to P-Town. You can fly into Boston’s Logan Airport and connect to the ferry or, alternatively, to Cape Air which flies (on a tiny plane) from Logan directly into P-Town (weather permitting) and is a 20-30 minute flight.
GT Tip: Check the calendar for theme weeks & weekends (like Bear Week, Girl Splash, Family Week, Carnival, et.al.) as the town can get quite busy and book up early during those dates — and just so you’re not surprised! If you are looking for a quieter, more chill getaway, you might want to avoid the busy theme weeks or July 4 weekend.
The Gimlet Traveler Rundown:
All ratings are based on our experience and are on a 5-star rating system (see Site Info for more details). For mapped locations and links to the places listed here (and more) visit Google Map at bottom of page.
Gimlets: *****
Many of our cocktail spots in Provincetown are also our favorite restaurants, as there are really only a few places in town that are dedicated solely to cocktailing (not including the clubs and the daily tea dance mentioned below). These “cocktail bars” include The Harbor Lounge, which is set back from Commercial Street and has lovely views of the water (and opens out to a long narrow outside deck); Aqua Bar, which while cocktail-centric, offers some raw bar selections and other casual snacks on their covered outdoor deck overlooking the water; and Shipwreck, the indoor/outdoor lounge located in the lobby and courtyard of The Brass Key (one of Provincetown’s premier lodgings). Shipwreck (and Brass Key) caters to a primarily LGBT+ clientele. They’ve got a firepit in their courtyard which our friends refer to as “the friendship circle” — having made numerous new friends (not a euphemism, mostly!) while sitting outside around the pit over the years. Restaurants where we could be happy with a great cocktail before or with an amazing dinner (some of which you’ll also see under restaurants below): happy hour at The Red Inn has become a little less informal during the pandemic (no more “show up, grab an Adirondack chair on the deck and order a few drinks”), but they still make a great cocktail and have delicious appetizers; Strangers and Saints which makes terrific cocktails in both their modern-rustic indoor and spacious outdoor terrace spaces along with shared plates and pizzas; the old-school bar at Jimmy’s Hideaway is intimate, cozy and welcoming; Pepe’s Wharf is a sprawling and beautifully decorated restaurant with a cute little bar and a smart living room/lounge/waiting area which would be a nice place for a pre-dinner cocktail (bonus points: in spite of a crowded room at dinner, the gimlet turned up exactly the way I like it). The Patio Grill, an ever-popular choice on Commercial Street that’s been revamped fairly recently with new owners and a fresh look, serves up delicious cocktails — some in mason jars (which my Southern husband always likes) — with lunch or dinner day and night. Also, Victor’s and Liz’s Cafe/Anybody’s Bar, both on Bradford rather than the busier Commercial Street make good cocktails, with Victor’s especially popular for its happy hour.
Moving onto nightlife… Tea Dance at The Boatslip kicks things off from 4-7pm, every day during the season, rain or shine. The tight indoor dance floor gets quite packed — which is part of the fun! The Crown and Anchor is a large complex in the center of town that contains a namesake hotel and restaurant, an outdoor bar for daytime drinking, a couple of cabaret spaces, an old-school piano bar, a video bar (Wave Bar, home to Musicals of Stage and Screen Video Nights) and a big dance club (The Paramount) — oh, and if that’s not enough, a leather bar (The Vault). Tin Pan Alley,is a cute restaurant (nice for lunch) with a small but popular and often crowded piano bar up front. The Crown & Anchor also has a popular and lively piano bar. If you prefer something more “old-school Provincetown” for dancing and drinking, visit the A-House. It’s in a rustic old building, but it’s still a big and popular dance spot. Adjacent to A-House is their Little Bar (just your basic dive bar) with the appealingly dark and also divey Macho Bar upstairs. Bars and clubs close at a civilized 1am, after which it’s common to stop at Spiritus Pizza (which is open another hour or so after the clubs close) for pizza and/or ice cream or just hanging out in the street.Restaurants: *****
New addition (as of summer 2023) Freeman’s, replaces the old Edwige restaurant in its intimate vaulted upstairs space in the east end. It’s a bit more upscale and refined, and doesn’t take parties larger than 4; I’m looking forward to trying their Parker House rolls! Ross’ Grill is an upscale, but still informal, American spot; with lovely views of the water from its back deck (be there for sunset). It’s a fave spot for dinner with friends (I’ve even had a couple of birthday celebrations there — including my 50th birthday dinner). The venerable Red Inn, located in the far west-end of P-Town. While great for a very casual happy hour cocktail overlooking the water as noted above, it is more of a special-occasion restaurant for dinner. It’s still casual like most everything in P-Town, but there is an air of formality to the menu and the dining room. Pepe’s Wharf has an expansive, stylish, modern-coastal feel, with multiple rooms, a cute bar, and an east-end Commercial Street location backing up right onto the water. The food and drinks were both excellent. The Patio Grill is a casual lunch/dinner/cocktail spot — always busy — located conveniently in the middle of town on Commercial Street, with outdoor and indoor seating and a reliably varied food and drink menu. Strangers and Saints, a trendy restaurant in the east-end, has a large outdoor dining terrace in addition to its modern-rustic indoor dining room and bar, and serves a causal menu of pizzas and shared plates. Jimmy’s Hideaway is a small, dark and very cozy old-school spot down a short path from Commercial Street in the center of town. They also have a small backyard outdoor dining area, but I like the cozy vibe inside or at the bar. The Lobster Pot is a classic (and large) New England seafood house. Put on your bib and dig in! There are often long lines at peak hours in high season, so be prepared. Victor’s in the west-end is known for its happy hour, which includes giant shrimp cocktail. Liz’s Cafe on Bradford Street in the west-end, has a relaxed surf-y vibe — good for dinner, but it may be even better for brunch. Other popular places: Cafe Heaven (great breakfasts, often a line for brunch), Canteen is a casual seafood shack with a cute backyard on Commercial, Spindler’s (East-End), Bubbala’s offers a very casual diner fare with a pleasant tree-shaded street-side outdoor dining area, Crown and Anchor (see “gimlets” section above) is a trusty standby for dinner with it’s covered outdoor dining smack in the town center.Sights/Landmarks: ****
While one usually doesn’t head to P-Town specifically to go sightseeing, there are nonetheless, some sights to see and an abundance of outdoor things to do. The Pilgrim Monument is a notable landmark in the center of town. You can climb to the top for a view over the town. If you’re a beach person, head to Race Point Beach where you can enjoy views of the coastline and enjoy the beautiful windswept dunes (see picture at top). The other choice is Herring Cove Beach, for warmer waters and nice sunsets (and is also, after much walking (sometimes involving wading through water), the location of the LGBT beach. For my 50th birthday, my husband and friends surprised me with a tour of the sand dunes of The Cape Cod National Seashore, led by Art’s Dune Tours. After a drive through the dunes in a 4WD SUV, you and your friends can gather around a small bonfire on the beach at sunset while watching seals in the water (your driver will make smores, but it’s up to you to bring the booze). I highly recommend it. In addition to the multitudes of art galleries lining Commercial Street from one end to the other, there is the Provincetown Art Museum located way down in the east-end. It has changing exhibits — many from local artists who have drawn inspiration from the Cape’s natural beauty. Long Point is an isolated area at the very, very tip of Cape Cod, complete with a historic lighthouse, quiet beaches, and breathtaking views. You either have to take a 20 minute ferry shuttle from MacMillan Pier or if you have more time to spend and are more adventurous, you can also hike to the area. There are numerous biking and hiking trails around Provincetown for those want to explore — including the popular Cape Cod Provincelands Trail which takes you over challenging dunes, through a shady beach forest and offers several miles of paved stretches for easy cruising.
If you are looking for a place to sunbathe, but prefer a pool, your two choices are either the large deck at the Boatslip (which also offers cocktails and basic food service) for a minimal charge or the free-of-charge, far-west-end Provincetown Inn, which has sun loungers and food/drink kiosks, as well as a small expanse of beach adjacent to the fenced pool area.
Every summer numerous Broadway performers can be found performing an intimate concert or cabaret show, whether at the Art House, Town Hall, or Crown & Anchor’s Paramount Club or Cabaret Room. Make sure to check schedules and purchase tickets in advance. Drag shows are also a perennial attraction at the same venues, including annual shows performed by Varla Jean Merman and Miss Richfield.
The main attraction of course is the town itself and it’s main thoroughfare, Commercial Street, which stretches from one end of town to the other. It’s filled with crowds of pedestrians vying with slow-moving cars, endless restaurants, shopping, bars and people-watching. Welcoming to everyone, P-Town really is a place like no other.Shopping: *****
Provincetown can be a very dangerous place for those who like to shop (i.e. The Gimlet Traveler!). Here are some of our favorites: Yates and Kennedy for classy home design stuff (we almost always end up going home with something from here); Tim-scapes where the colorful, blocky and unique designs originated as art that founder Tim Convery created with duct tape, and now appear on apparel, mugs, beach towels, and as framed prints; Loveland, a small shop in the west end with a curated collection of trendy men’s and women’s clothing, home goods and tote bags; MAP, a small, classy shop with modern men’s clothing, bags, cards, and gifts; Room 68, for modern, well-curated art and objects for your home, Henry & Co for upscale-casual men’s clothing and shoes; Tom Sharp creates and sells his own witty and comfortable t-shirt designs from his small boutique in the west end; John Derian is famous for his glass decoupage trays and paperweights, but this iteration of his boutique, set back from Commercial Street, also sells colorful textiles and other decorative items; also, Arcadia for attractive home design gifts and Shor another upscale home design shop with a New England beach-house aesthetic.
B&Bs / Hotels:
Eben House Rating: ***** (PERMANENTLY CLOSED!).
Eben House is smack in the center of Provincetown (a 2 to 15 minute walk to most anywhere on Commercial Street) with a cute little pool (rare in Provincetown), a small sundeck, and a cozy breakfast space. Our room was small, as was the bathroom (there are other, larger rooms), but it was all well laid out and nicely designed in a quirky and fun New England contemporary style. Enjoyed our short stay. Cute and convenient.
Date of stay: September 2017
Room tip: Upstairs if you want more light, and ask for one of the larger rooms
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8 Dyer Rating: *****
8 Dyer is located on a pleasant, quiet block towards the east end of Provincetown. While the rooms are not huge, they are classy and nicely appointed. Certain rooms have a loft with a tub or a fireplace, others may have an outdoor terrace. We loved room 10 (see below). The biggest selling point is the lovely pool out back, which has sun loungers and which gets a good amount of sun.
Date of stay: June 2009.
Room tip: Room 10 is modestly sized, but has a large private terrace overlooking (and with steps down) to the pool, as well as a fireplace. Bathrooms are small.
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Other Hotel Choices:
• Brass Key Guesthouse — high-end lodging with outdoor pool, jacuzzi, and a popular bar (the Shipwreck Lounge).
• Carpe Diem Guesthouse and Spa — outdoor jacuzzi, private courtyard with loungers and popular day-spa
• AWOL Hotel — a new 30-room upscale boutique hotel on far west-end of town - modern rooms, nice pool and small bar.
• Crowne Pointe Inn — spread over a few Victorian buildings, with small pool, restaurant, and on-premises day spa.
• The Red Inn — Right on the water in the west end, the popular restaurant has four guest rooms and two luxury suites.
Below is a map of hotels, restaurants, bars, shopping and sights found during our research. We didn’t have time to visit all of them during our trip, but all were of interest. Click on the icon at top left of the map to view the legend. Or you can click on the full-screen icon at top right to expand, which will also bring up the legend.
