What to expect your first time visiting Provincetown

While several destinations may be considered summer rites of passage for gay travelers, Fire Island, Saugatuck, and Provincetown are probably the big three in the United States. But for those of us who were never indoctrinated in these places as young gays, is it too late?

My husband and I (we’re in our 40s and 50s), along with some friends, decided that there’s no time like the present, and we jumped at a chance to visit Provincetown this summer. The idyllic art colony, located at the tip of Cape Cod, hosts various themed summer weeks, such as Bear Week, Girl Splash, and Family Week.

Planning it right

Pack your bags, we’re going on an adventure

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We decided to make it a four-day weekend, flying into Boston and driving the 2.5 hours to Provincetown. There’s also direct ferry service from Boston to Provincetown, and we’ve heard great things about it, including that the Provincetown party atmosphere starts right on board. But our flight times didn’t jive well with the three-time-per-day ferry service, and with four of us, the car rental came out at about the same price. Plus, as we’d never been to Cape Cod, the car allowed us to explore a bit. And we did, stopping in Quincy to try a lobster roll, pausing in Plymouth to see that certain famed rock, and taking a couple of side turns to check out some beaches and overlooks.

 Our planning was a bit last minute, so we relied on Airbnb for our lodging. I was pleasantly surprised to find a reasonable home right in the center of town that perfectly met our needs. Although it included a parking space, we could walk to everything in town easily. Parking is truly at a premium in Provincetown, so the next time we return, we’ll likely take the ferry and not worry about a car.

Make sure to research the various theme weeks early in your trip planning process, as lodging options will sell out well in advance for some of them. For foodies, it’s also advisable to make reservations at hot local restaurants weeks in advance.

The vibe

I wasn’t sure what to expect from Provincetown, but I immediately liked its vibrant atmosphere. Commercial Street is one of the main focuses, with endless bars, restaurants, art galleries, and shops. You’ve likely seen streets like this, but the sheer length of the busy part of Commercial Street is unbelievable.

Pedestrians spill off the sidewalks and into the street, competing with the occasional one-way traffic, bikes, and frequent pedicabs, many helmed by young shirtless drivers, who obviously know their audience well. My husband was particularly impressed by one who looked like he could have been a Men’s Fitness cover model, and trying to catch him became a bit of a running joke on our trip.

Provincetown also has that feeling that Palm Springs exudes, where the queer population and visitors are every bit as prevalent as the straight folks — and no one cares a bit. It’s liberating and freeing in a way you don’t quite anticipate until you experience it.

And Provincetown is small and quirky, too, where you chat with a cool lesbian masseuse at an art gallery one night and then run into her on the street the next day. Or where you strike up a conversation with a fellow who turns out to be the husband of drag star Ginger Minj. And where you head to dinner and realize that Sandra Bernhard and Jennifer Coolidge are sitting two tables away. (Yes, we were a bit starstruck but behaved ourselves.)

Related

The gay-friendly guide to Cape Cod (beyond Provincetown)
Cape Cod’s welcoming spirit extends beyond its popular towns.

First timers’ activities

There’s a lot to do in Provincetown, including simply relaxing and doing a whole lot of nothing, which is totally acceptable on a vacation. There are plenty of gay bars here, but we primarily focused on other activities. Here are some of our highlights from our time in town:

Do the dunes — Art’s Dune Tours is a local company that has been operating for over 75 years. Their daily dune tours run for about an hour and let you experience the fascinating landscape of the Cape Cod National Seashore. There are also sunset tours and additional excursions offered. Our guide, Johannes, was fun and insightful, and also shared his stories of moving to Provincetown many years ago from his native Germany.

Take in a drag show — There’s so much drag (and drag adjacent) here. You can choose from plenty of local performers or visiting queens with national recognition. We saw the “Everybody Loves Jujubee” show at the Art House Theater, an hour-long show featuring the Drag Race star regular from nearby Boston. She mixed some light stand-up with a variety of singing, and we all enjoyed the performance.

Art it up — Each Friday, wander along the east end of Commercial Street (from Johnson Street to Bangs Street) for the Friday Night Gallery Stroll. You can visit multiple galleries from 6 to 9 p.m., many of which serve wine, cheese, and fruit. And if you miss that during your visit, you can still get your fill of art at PAAM, the Provincetown Art Association and Museum. This lovely facility has a permanent collection that focuses on older works (including many fisherman and nautical themes) and regularly switches out its temporary exhibits.

Dance the night away  — There are frequent tea dances at the Boat Slip Beach Resort. A local advised us to try the rum punch and head to the main bar’s right side, where Maria “does a heavy pour, so all the boys line up for her.” They weren’t kidding, and a single one of Maria’s concoctions almost had me on the floor. There was a $10 cover charge (cash only) when we went, and the event was from 4 to 7 p.m. We were advised to go no earlier than 5 p.m., which was good advice. The difference in the crowd, even from 5 p.m. to 6 p.m., was incredible, with almost no space to move by the end of the evening.

Get a little high — The 252-foot-tall Pilgrim Monument is visible from all over the city and is a local icon. Along with the Provincetown Museum, it’s well worth a visit and a climb up to the top, where you’ll have sweeping views of the whole cape.

Come on, beach — Race Point Beach and Herring Cove Beach are the two main beaches here. After talking with locals, we decided to spend an afternoon at Herring Cove, which has more facilities (including some food). If you walk about ¾-mile down the beach, you’ll come to Boy Beach, an unofficial nude beach where many of the queer visitors prefer to hang out (sorry, pun intended).

On our last night in town, we finally managed to hail down the sexy pedicab driver — Tony, it turns out — who hails from Eastern Europe. We also chatted with a couple of others, who told us they specialized in massages, including the kind with a … well, let’s say, a pleasant finish. Clearly, theirs is a bustling business, based on how forward they were about it. Sadly, Tony never offered such services, so we stuck to using him for transportation, admiring the view from our seats as we cruised through town.

Henry David Thoreau said that when you stay in Provincetown, the “sandy fist” of Cape Cod, you leave all of America behind you. That was the feeling we had here, and it was lovely to leave the politics, work stress, and life responsibilities behind for a few days. Provincetown, we’ll definitely be back.