Gay Provincetown Travel: Gay Bars, Hotels, Culture & History

The Out Of Office guide to America's best town for a gay vacation.

Provincetown is the best small-town destination for gay travellers in the USA. It’s long been hailed as one of the most liberal towns in the country, and it’s a big draw for artists and bohemians: gay-popular hotspots tend to begin as artist hotspots. Think Mykonos, Key West and Sitges. Over time, Provincetown has become more of an upmarket destination than a haven for struggling painters.  It’s a town of steadily rising house prices and rowdy, cruisey bars.

What is Provincetown known for?

2020 marked the 400th anniversary of a world-changing event. A boat full of storm-tossed pilgrims arrived from England and docked in Provincetown harbour. The rest, as they say, is history. These enterprising Protestants signed the Mayflower Compact in Provincetown. They would ultimately forge the United States of America. Little did they know that their landing place would later be overcome by shirtless gay men covered in glitter, but things never quite pan out the way you expect.

Provincetown is a fabulous year-round destination. Known by locals and regular visitors as “P-town”, it’s located at the tip of Cape Cod in one of the most remote destinations in the USA. Curiously, Key West, another art and LGBT+ capital, is also located in one of the most remote parts of the country. Anyhow, Provincetown has a number of excellent beaches, charming B&Bs and lots of gay bars. In peak season straight people are very much in a minority.

P-town emerged as an unlikely hotspot after the 1898 Atlantic hurricane season. A huge storm wreaked havoc on the town so it was repositioned as a tourist destination. Many artists and bohemians flocked to the Provincetown – no doubt attracted by the remote setting and flawless light. The gays soon followed. By the 1920s, Provincetown was certifiably queer. Incidentally, Provincetown is John Waters’ second home, so keep an eye out for the pencil tache.

The best time to visit Provincetown

Provincetown is small. Out of season it has a permanent population of around 3000. There are probably more people dancing in Industry in New York on a Friday night! During peak season the numbers swell to about 60,000. A lot of businesses only open from May to October. July and August are the busiest months. Things cool off a little in September, but Provincetown will be buzzing although less crowded. The weather is still excellent, too. As the gays sure love Halloween (blame Bette Midler), October is also a good time to visit Provincetown. This is a town that takes Halloween seriously.

Supposing you’d like to avoid the crowds, a winter trip to Provincetown can be very romantic. The landscapes of Cape Cod are stunning. The town itself covers a mere 3 square miles. Venturing into the countryside you’ll find many trails to explore, such as trips to Long Point Lighthouse and the Pilgrim Monument. If you’re all about the scene then visit Provincetown in peak season. But if romance, cosy inns and long walks are your thing, then there’s never a bad time to visit Provincetown.

How gay-friendly is Provincetown?

Very! It may well be the top gay vacation spot in the USA. Along with Key West, Sitges, Mykonos and Puerto Vallarta, it’s one of the most gay-friendly places on earth. Its economy is largely sustained by tourism, and most P-town tourists are gay. It’s not much of a stretch to describe Provincetown as a gay town. Question: why are gay-towns always the most fun, arty and glamorous?

Provincetown’s gay scene and nightlife is centred around Commerical Street. The Crown & Anchor Entertainment Complex comprises several gay bars and a hotel. In the summer months shirtless men can be seen spilling out into the streets, lounging around the pool and dancing by the seafront.

Paramount is the largest gay club in town and it hosts the opening party for the Provincetown International Film Festival. It also hosts cabaret and drag shows. You’ll see queer performers from all over the USA and the occasional big name act, such as Alan Cumming.

Other places that are like Provincetown

Love your gay vacations in Provincetown and fancy trying somewhere else? You can experience the quaint yet fabulous small-town vibes in the old world too. As LGBT+ Americans flock to Provincetown, LGBT+ European flock to Mykonos. That being said, you’ll encounter a lot of American travellers in Mykonos. The Greek island of Mykonos is impossibly chic, the climate is flawless and it has a great selection of luxury hotels. You can visit the nearby island of Santorini if you’d like to experience a more romantic and laidback trip.

You can join one of our ever-popular gay group trips to the Greek islands. We can also guide you through the best hotels in the Greek islands if you’d like a tailor-made itinerary. You can also check out our blog contrasting Mykonos and Santorini. Anyhow, let’s get back to Provincetown.

What’s happening in Provincetown?

Theatre, darling. It’s a town dedicated to pleasure and leisure. The Art House hosts much of the best theatre in Provincetown. Here you’ll see big stars from Broadway and Drag Race alumni. Many of the shows are geared towards gay audiences: think Patti LuPone singing Ladies Who Lunch and Jeremy Jordan doing tracks from Broadway Loves Celine Dion. That kind of level.

The Cabaret Room at the Crown & Anchor hosts some great cabaret and drag shows. Favourites include Thirsty Burlington as Cher, and comedy icons like Margaret Cho and Lisa Lampanelli.

How to get from Provincetown to Boston

Boston is the largest city in Massachusetts. The fastest way to get from Provincetown to Boston is by ferry. The ferries run roughly 18 times per week and take just 1 hour and 30 minutes. Boston is one of the oldest cities in America. It has a big cultural scene, not to mention a welcoming gay scene. Boston is, of course, famous for seafood. Make sure to try oysters with chowder. This city played a key role in America’s revolutionary war against Britain and you’ll see monuments to the key battles and generals throughout.

There are many great destinations to explore in Cape Cod and Massachusetts more broadly, such as Martha’s Vineyard. It’s a charming island that’s long been a draw for artists and bohemians. Martha’s Vineyard attracts a different kind of bohemia than Provincetown. More of an upper-class bohemia, best exemplified by Carly Simon, a long term resident. It’s one of the most upmarket destinations in the USA.

Another favourite Massachusetts destination is the island of Nantucket, famed as the home of Arthur Gordon Pym, the protagonist of Edgar Allen Poe’s only novel. It’s also the starting point of Ishmael’s voyage in Moby Dick – fitting, as it was once a centre of the whaling industry. Today, Nantucket is a preppy haven, so bring a pastel jumper. It’s a great place to sip cocktails, eat seafood and relax. The average house price in Nantucket is $1,701,700, as of 2020.

You can combine these destinations if you’d like to do a road trip around New England. Getting to and from Nantucket and Provincetown is time-consuming, so you can’t really opt for a day trip. Either stay in Provincetown, combine Provincetown with Boston or go for a full-on road trip for the optimal New England experience.

Provincetown may be small but it has more than enough action to keep you occupied. It can be twinned with other places but when you arrive, you won’t want to leave. It’s the kind of place where gay dreams true.

Crowne Point Inn


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