The Palm Springs Guys Travels — Blog

**Gregory & Glen (aka The Palm Springs Guys)**

There is nowhere on earth quite like Palm Springs when it comes to living your best gay life. We say that with full confidence, zero hesitation, and the full-time living perspective. With nearly 50% of the population now identifying as LGBTQ+, 350 days of sunshine per year, and a built-in community that greets you like a chosen family, Palm Springs is genuinely in a category of its own. It is the kind of place where you gaycation, exhale, and start imagining what it might feel like to never leave. We know, because that is exactly what happened to us.

But we also love to travel as much as the next because the world is full of extraordinary places, people, and food to explore – and we want to share our experiences with the community we love. So alongside everything we bring you about our home base in the desert, we are also occasionally spotlighting other great gay destinations through the lens of our own travels as an additional resource for anyone planning their next adventure.

Which brings us to a personal favorite of ours: the small hamlet of Cape Cod at the cape’s tip – Provincetown, Massachusetts. 😎

TL;DR 😜

Glen and Gregory spent 3 nights in Provincetown this past summer – their first return visit in nearly a decade. They took the fast ferry from Boston, stayed at two very different (and both wonderful) properties, ate generous amounts of seafood, saw some of the best comedy queens in the business, explored both ends of Commercial Street, and left already plotting their return. Here's the full story, with every detail you need to plan your own P-town adventure.

Destination Provincetown

Provincetown sits at the very tip of Cape Cod – that iconic arm of land curling out into the Atlantic Ocean off the southeastern coast of Massachusetts, about 120 miles from Boston. It is one of the smallest towns you will ever fall completely in love with, occupying just under 20 square miles with a year-round population of roughly 3,000 people – a number that swells dramatically each summer as gay men, artists, families, and free spirits of every variety descend on its narrow streets with great enthusiasm and very little agenda. Commercial Street is the town's main artery, lined with art galleries, restaurants, bars, boutiques, and an ever-rotating cast of characters that makes people-watching here a highlight of the trip. Provincetown is, in every meaningful sense, a place that operates on its own terms – and has been doing so for a very long time.

Getting There: Take the Fast Ferry

Since we flew into Boston, we decided to try Boston's Provincetown/Cape Cod Fast Ferry for the first time – and it is now our permanent recommendation. The alternative options are a short flight via Cape Air or driving up the cape, which can take upwards of four hours in summer traffic (and frankly, who has the patience for that kind of energy before a vacation?). The fast ferry, by contrast, is a 90-minute ride each way, weather dependent, with both airplane-style seating and table seating with power outlets and high-speed internet. On the round trip alone, we got three hours of work done, which meant we could be fully present – cocktails in hand, not laptops open – for every moment in town.

Provincetown is also one of those rare destinations where having a car is genuinely more trouble than it's worth. The town is extraordinarily walkable, Commercial Street is the spine of everything, and parking is a challenge of the most charming variety. Consider extending your vacation with a ferry ride, grab a drink at the ferry bar, and enjoy the water.

Before boarding, we grabbed lunch at Chart House at Long Wharf – the oldest surviving structure on the wharf, now a high-end chain eatery with harbor views and a menu that punches well above its chain-restaurant expectations. The heirloom tomato and burrata crudo with toasted pistachios was as refreshing and fabulous as the Chef's special: a miso-glazed catch of the day over sautéed Asian-inspired vegetables in a rich seafood broth. One of the best meals of the entire trip, actually – which set a high bar for everything that followed.

What’s the Deal with that Tower?

Here is something that surprises most visitors: Provincetown, not Plymouth, was where the Pilgrims first landed in America.

In November 1620, the Mayflower apparently reached the tip of Cape Cod after a grueling Atlantic crossing, anchoring in what is now Provincetown Harbor. It was here, still aboard the ship, that the Pilgrims drafted and signed theMayflower Compact – the foundational document of American self-governance that is often considered a precursor to democratic government as we know it. For about five weeks, exploration parties fanned out across Cape Cod searching for a suitable settlement site, before ultimately determining that Plymouth offered better long-term resources.

Towering over the town today is the Pilgrim Monument – at 252 feet, the tallest all-granite structure in the United States, completed in 1910 and inspired by the Torre del Mangia in Siena, Italy. Visitors who climb its 116 steps and 60 ramps are rewarded with sweeping views of Provincetown, Cape Cod Bay, the Atlantic Ocean, and the surrounding dunes. Seeing it rise above the rooftops for the first time feels like spotting a lighthouse in the distance – like the town's own Lady Liberty, or perhaps more fittingly, its own Forever Marilyn: a warm, monumental, and slightly queer welcome hug.

There is something profound about the fact that this granite monument to one of America's earliest colonial stories stands directly above one of its most vibrant, creative, and liberating LGBTQ+ communities. Over the centuries, Provincetown evolved from a fishing village to an important artist colony – drawing theater-makers, painters, and writers – and eventually into one of the most significant gay destinations in the country. The full arc, from Indigenous Wampanoag heritage to Pilgrim history to maritime culture to queer community-building, makes Provincetown a layered, textured place in a way that most tourist towns simply are not.

We couldn't help noticing the parallels to our own beloved Palm Springs – another small, seemingly unassuming town with a similarly pioneering history of cultural heritage, self-expression, and hard-won inclusion, as beautifully chronicled in Anita Doll's Five Eras of Palm Springs. Two unassuming small towns with drastic differences (desert vs. ocean, modernism culture vs. maritime culture) – both with pioneering eras of colonization, cultural heritage, inclusion, and self-expression that are distinct to their own.

Welcome to Provincetown: Day 1

The ferry docks right at the center of town, and in less than five minutes of walking along the pier into the heart of it all, we spotted Dina Martina– one of Provincetown's most legendary drag queen staples and our all-time favorite comedy queen – out of drag and strolling through the street like a civilian. We managed to keep our composure, knowing full well we'd be seeing her show before the trip was over.

Our first stay was at the Gaslamp Bed & Breakfast – a renovated Victorian-style boutique B&B in the heart of Provincetown, built in the late 1800s, with seven stylish guest rooms, each with a private bathroom. That last detail matters because a significant number of P-town guest houses operate with shared bathrooms, so the privacy at the Gaslamp felt like a real luxury. The owners, Jeff & Jim, greeted us with exactly the kind of warmth you want to set the stage for a fabulous trip. The rooms themselves can best be described as historic charm with modern sophistication – each with its own stylish theme, a spacious walk-in shower with luxury bath products, AC, smart TV, mini refrigerator, and a memory foam mattress that we happily sank into at night. And breakfast each morning was a daily culinary delight (more on that shortly).

We kicked off our P-town adventures with a stroll south down Commercial Street, taking in everything it had to offer: the shirtless boys driving pedicabs, the art galleries, the bars, the restaurants. We browsed through shops like Whalers Wharf, Toys of Eros, and the ST33LE flagship – always a dangerous stop for anyone with a weakness for very well-made short shorts.

We made our way down (west) to the iconic Boatslip Resort for their legendary tea dance, only to discover we had arrived slightly too early in the season for it to be in full swing. We enjoyed cocktails at the bar instead and watched drag queens “bark” (it’s a thing) at tourists to promote their summer residencies. Within the same twenty minutes, we spotted both Tina Burner and the legendary Sherry Vine – which felt like an omen of excellent things to come.

Dinner was at Ross’ Grill – a local favorite running 25 years strong with breathtaking harbor views, a European bistro atmosphere, 60 wines served by the glass, and some of the freshest, most carefully prepared seafood we'd had in years. A first-class dining experience, with some of the best scallops we’ve had a long time.

The evening took an unexpectedly sexy turn when we wandered into Crew's Quarters – Provincetown's most unique historic gay boarding house, located at the corner of Commercial and Carver Streets and a gay landmark for over 65 years. We were initially drawn in by one of the most creative marketing moves we'd encountered: a vintage black-and-white film that was being silently projected onto the brick building next door, peaking our curiosity. What we discovered inside was a seductively lit speakeasy bar doubling as a reception desk, a common area open to the public and guests alike, and an atmosphere that managed to be simultaneously warm, intimate, and subtly cruisy in the most delicious way. The stylish owner and conceptual mastermind welcomed us to do a full self-tour – and exploring their rooms completely changed our perspective on the shared-bathroom boarding house concept. The bathrooms felt more like a classy gay men's bathhouse than an inconvenience. We will certainly be testing the waters with a future stay.

We capped the night at the Atlantic House (aka the A-House) – a P-town staple for dancing and cruisy evening energy, conveniently located right next door to the Gaslamp. The A-House is widely considered one of the oldest gay bars in the country, with roots stretching back to the early 1900s when it first began drawing those who lived life a little differently than the mainstream expected. By the early 1950s, the A-House had fully embraced its identity as a gay-friendly landmark, and it has never looked back. Today it operates as a wonderfully unlikely combination of party central and neighborhood bar – hosting weekly themed nights in its larger disco room, while the intimate Little Bar keeps its own cast of beloved regulars. Upstairs, the Macho Bar caters to the leather crowd and their admirers. In summer, the patio opens up and the boys descend nightly to dance, drink, and get to know each other in the way that only P-town makes feel completely effortless. No visit to Provincetown is truly complete without at least one night at the A-House.

On our (very short) walk back to the Gaslamp, the Pilgrim Monument illuminated like a haunting ghost through the fog on our walk home. It was epic to say the least!

Provincetown: Day 2

After one of the most comfortable sleeps we'd had in recent memory, Glen brought me coffee in bed from the Gaslamp's coffee bar – just one of example of what a gentlemen Glen Nadeau is – followed by the first of several memorable Gaslamp breakfasts: French toast with strawberry rhubarb compote (which we are still drooling over). We were fueled and ready for day two!

The day included more exploring and shopping – a return trip toST33LE (finally ready to make the purchase), and a mandatory stop at the Provincetown Fudge Factory for their world-famous dark chocolate peanut butter cups. As a confirmed chocoholic, I (Gregory) can report: the dark chocolate did not disappoint.

Lunch was at Johnny Thai’s Monkey Bar for sushi and house-made dumplings – generously portioned, beautifully fresh, and exactly what we needed before continuing our stroll even further west.

We also made a pit stop to get a daytime glance at P-town's infamous Dick Dock – which is found directly under the Boatslip Resort's deck, in case you were wondering and didn't want to ask. We'd potentially be revisiting this spot later in the evening ;)

Perry’s Fine Wines & Liquors

Joe Coffee

It was genuinely fun to spot some brother Palm Springs companies along our walk – Ball Beachwear and Perry’s Fine Wines & Liquors, both of which originated in Provincetown and now have locations in our hometown. We also stopped into Joe Coffee – a P-town institution currently planning its second location right here in Palm Springs on Sunny Dunes, across the street from Tool Shed. The coffee is excellent, the baked goods are the real deal, and the smiling boys behind the counter know how to make you feel welcome. We cannot wait for their Palm Springs grand opening.

On the stroll back, we crossed paths with another legendary queen: Varla Jean Merman, out of drag, walking her dog and adjusting her own promotional poster in front of the Crown & Anchor – a poster prominently featuring both her and the dog for her "Unlike A Virgin" show. I couldn't resist walking up to her and saying, "Your dog's more recognizable than you are right now." She laughed loudly and said, "Exactly!" It’s safe to say that making a legendary comedy queen genuinely LOL is a satisfying life experience!

Worth noting: gay-owned and operated Tryst Hospitality recently acquired the Crown & Anchor property to keep it out and proud. Tryst CEO & Founder Tristan Schukraft put it beautifully: "There's nowhere in the world like Provincetown. It's a place where LGBTQ+ people have come for decades to be seen, to create, to fall in love, and to live openly. The Crown & Anchor is at the heart of that story; it's been the stage, the dance floor, and Provincetown's unofficial town square. Our goal is to honor that legacy while evolving it for the future, ensuring it remains a vibrant, inclusive home for generations to come." We're here for all of that!

After a brief siesta at the Gaslamp (because P-town is a marathon, not a sprint), we made our way to Joon Bar & Kitchen for an early dinner. The vibe was seasonal New American with a Mediterranean-inspired, globally influenced menu in a sleek, stylish space. I opted for the local seafood bouillabaisse; Glen went with a green curry chicken and black-eyed peas special. The food was layered and rich with flavors that reached well beyond the average dish.

Then came the night's main event: Nina West at the Post Office Cabaret in her comedy parody "Oh, Scary!" – which was, in fact, genuinely scary in ways that still haunt me to think about (was that really a singing vagina?!? I'll let that linger). The Post Office Cafe & Cabaret has been a Provincetown landmark for nearly 50 years, and the intimate theater space made for an immersive and slightly intoxicating experience throughout the show. The venue itself has a fascinating history – originally the Lands End Marine Supply in 1940, converted to the Wreck Club in 1960, and brought to life as the Post Office Cabaret in 1974 by theater MFA and educator Phyllis Schlosberg, who used the stage to launch careers including Varla Jean Merman and Elvira, Mistress of the Dark. The list of performers who have graced that stage since then – Eartha Kitt, Lea DeLaria, Divine, Trixie Mattel, Raja, and many others – reads like a drag hall of fame.

We continued on to Lady Slipper – a pretty-in-pink cocktail spot that describes itself as "Elegant… for Provincetown." Beyond its extremely understated website, we'd argue it's elegant for anywhere. The drinks were as creative and thoughtfully presented as the décor, the bartenders were genuinely charming (shake that shaker, gurl!), and the scene was intimately lively in all the right ways.

We wrapped up at the Gifford House, which houses Club Purgatory, Porch Bar, and Wilde Playhouse. We happened to catch "Cowboys," a one-man burlesque show on the outdoor stage – which was underwhelming at best, but the crowd more than compensated.

After an intoxicating evening of social exchange and general flirtation, we decided to see what Dick Dock is really like at night. The short answer: the boys don't show up until after the bars close, so we were early to the party (yet again, lol). So I guess we had to learn that the hard way (and not in a good way).

Provincetown: Day 3

After another memorable Gaslamp breakfast – truly, Jeff & Jim have an effortless gift for this – we packed up and moved east to our second and final lodging: Charm, a lovely guest house tucked away on the quiet side of the street. Clean rooms, easy self check-in, and a thoughtful $5 per-day/per-guest voucher for breakfast use at Far Land Provisions – a charming corner store and deli with an on-site bakery, prepared foods, and made-to-order breakfast sandwiches that were worth the wait for.

We spent the day exploring the eastern stretch of Commercial Street, beginning with a visit to the Provincetown Public Library – which holds a delightful surprise on its second floor. Spoiler: it's a ship. A very large ship. TheRose Dorothea, designed by Thomas McManus and built at the Tarr & James Shipyard in Essex, MA in 1905, is 108.7 feet long, weighs 108 tons, and takes up the entire second floor space. Before her permanent residency at the library, her rounded bow enabled her to sail closer into the wind than other schooners of the era, making her faster and more agile than her competitors. We think she would have made both Rose and Dorothy proud (see what I did there)?

For lunch, we happened upon Ocean 193 – hiding back behind a walkway just off of Commercial Street – for more spectacular seafood and ocean views that did not disappoint. The fish tacos were superb, and their Arnold Palmer’s were some of the best we’ve had (we have a deep appreciation for a good Arnold Palmer).

We continued through shops like the unique and stylish MATE Provincetown and made it to E. Lesh Gallery, where we had the opportunity to meet Eric Lesh himself and browse his striking collection of provocative male nude paintings.

Then – finally – tea dance. The Boatslip's legendary afternoon tradition kicked off with a dog tag theme, and some of the crowd fully committed to it. The energy was exactly what you'd hope for: boys trickling in, drinks beginning to flow, the afternoon sun setting the stage. You haven’t done Gay Provincetown if you haven’t done tea dance. Mission accomplished. But we couldn't linger for too long because one of the most anticipated moments of the trip was upon us.

Dina Martina's new show, "Absolute Dina Martina" – presented in the Paramount at the Crown & Anchor – was next up. She is, truly, impossible to compare to anyone else. Her particular brand of absurdity is extraordinarily smart comedy packaged – sometimes – in a very tragic orange jumpsuit. When people say "Don't walk… RUN!" for a Dina Martina show, please receive that as a sincere and urgent travel advisory. The only real question is whether you can handle it. Photos of Dina were playing tribute all throughout Provincetown during our visit, like gentle jifts, which we found deeply appropriate (if you’re reading this, Dina, you’re welcome)…

Dina Martina photo by David Belisle

Our final dinner was at Front Street – a chef-owned restaurant with a lively atmosphere, modern nautical artwork, and a menu of classic Italian food and eclectic Continental favorites. We requested a table outside, which proved to be the right call entirely: the air was fresh, and the light was hitting the water at precisely the right angle, illuminating sailboats in the distance while we ate. I stayed consistent and went for the Zuppa di Pesce; Glen ordered the Braised Beef and Short Rib Ravioli. Both were spectacular, and we agreed it was the best meal we had in town. Not a bad way to close out a trip!

We still had one more show to catch: Miss Richfield 1981 at the Post Office Cabaret, in her show "You Can't Have Ice Cream When You're Dead." We had never seen Miss Richfield perform in all our years, and we were not leaving the cape until we had. Ice cream was, as you might imagine, a theme throughout. Whether or not it is possible to make ice cream genuinely funny remains an open debate, but her impromptu crowd work was a genuine standout – and there is something truly refreshing about watching an experienced comedy queen in total command of a room.

By the time we walked past an actual ice cream shop after a show about ice cream and were too exhausted to go in, we knew it was time to rest. Charm was a peaceful place to land for the final night of our stay.

Leaving P-Town (The Hardest Part of the Trip)

The morning ferry back to Boston was lovely once again. We couldn’t have asked for better weather throughout the entire trip – and we were continually reminded by locals that this was unseasonably warm for P-town in early June. Watching Provincetown fade off into the distance is the kind of moment that sits with you – and this was the first time in a long time that we found ourselves somewhere we weren't ready to leave. That particular feeling is a gift, and we are choosing to let it pull us back again next summer.

As of the time of this article’s publishing date, Provincetown's summer season is still in full swing – and if you are reading this with even a flicker of curiosity, we hope you go. Stay somewhere with a personality. Eat all the seafood in the ocean. See at least one drag show. Walk all of Commercial Street in both directions. Say something to the person next to you at the bar. You will not regret a single moment of it.

A heartfelt thank you to everyone in Provincetown who helped accommodate our stay and made this such a memorable gaycation. 🏳️‍🌈

Back to Palm Springs

We can't help but close with a love letter to our own backyard because the magic of Provincetown, in many ways, feels like a bridge back to Palm Springs.

While Provincetown offers a glorious few months of summer gaycation realness, Palm Springs delivers 350 days of it with virtually no seasonal asterisk. Our winters are the envy of the Northeast, our spring is incomparable, and even summer – once you learn its rhythm – rewards those who embrace it. If you haven't already, the cultural life here runs year-round: world-class dining, Modernism Week, the Palm Springs Art Museum, extraordinary spa culture, beloved gay resorts, and a nightlife scene that makes every night feel like a special occasion.

But what really draws gay men back to Palm Springs again and again – and increasingly persuades them to stay – is the community. With nearly half the population identifying as LGBTQ+, this is a place where gay men are the majority. You feel it the moment you arrive. Friendships form easily here. Connections run deep. New arrivals are welcomed like family, because that is precisely what this community has always been: chosen family, built intentionally, over decades.

If Provincetown has ever made you feel completely, unapologetically at home, and you’ve thought, "I need more of this in my life" – then Palm Springs might be a consideration you haven't had yet. For those on the East Coast who make the annual summer pilgrimage to P-town, consider this a warm and enthusiastic nudge from two guys who live in the gay paradise year-round: the desert is calling, and it would like you to stay longer than a long weekend.

Palm Springs is the place where a vacation has a funny way of suddenly becoming a vision for your future – whether that means a getaway home, a permanent relocation, or simply a place worth investing in earlier than most people realize. This is a values-aligned community in a city built for people who have always known what quality of life is actually worth. P-town will always have our hearts. But Palm Springs has our address. 👨🏼‍🤝‍👨🏻🌴

Have you ever been to Provincetown? Share your experiences…

If you're curious to learn more about all the fabulous fun waiting for you here in our gay desert home – including where to stay, what to do, and whether living here might be the next right move for you – check out some of our favorites on the blog:

Frequently Asked Questions About Provincetown, MA

Q: How do gay men typically get to Provincetown from Boston?

A: The most popular and recommended option is theBoston Provincetown Fast Ferry, a 90-minute boat ride that departs from Long Wharf in Boston and arrives directly in the heart of Provincetown. The ferry offers table seating with power outlets, high-speed internet, and a bar on board. Alternatively,Cape Air offers short flights, or visitors can drive – though summer traffic on the cape can add hours to the journey. Once in Provincetown, a car is usually unnecessary; the town itself is entirely walkable.

Q: What are the best places to stay in Provincetown for gay men?

A: Provincetown has a wide range of accommodation options specifically catering to gay travelers, from classic B&Bs to historic gay boarding houses. TheGaslamp Bed & Breakfast is a notable beautifully renovated Victorian boutique B&B with private bathrooms in every room and exceptional hosts.Crew's Quarters is Provincetown's most historic gay boarding house – a 65-year gay landmark with shared bathrooms, a speakeasy reception, and a uniquely intimate, social atmosphere.Charm offers clean, comfortable rooms on the quieter eastern end of Commercial Street with easy self check-in.

Q: What is tea dance at the Boatslip in Provincetown?

A: Tea dance at the Boatslip Resort is Provincetown's legendary late-afternoon outdoor dance party, held daily during the summer season. It typically runs from around 4:00 PM to 7:00 PM on the Boatslip's waterfront deck and is considered a quintessential P-town experience – an essential rite of passage for any gay man visiting the cape.

Q: Is Provincetown worth visiting for gay men of all ages?

A: Without question. Provincetown is one of the most genuinely welcoming LGBTQ+ destinations in the world – and one of its greatest qualities is that it has something meaningful to offer gay men at every stage of life. In your twenties, P-town is a revelation: a place where being gay is simply the default, and the energy is intoxicating. In your thirties and forties, it deepens into something more layered – world-class drag entertainment, extraordinary seafood, a thriving arts scene with over 40 galleries, whale watching, dunes, and a social atmosphere that is unhurried and genuinely connective. And for those who are 50+ or looking for a slower pace, P-town rewards this beautifully with long dinners, afternoon tea dances, cultural experiences, and conversations that linger. Its walkable scale and rich LGBTQ+ history make it well worth planning a trip around any time from late spring through early fall, regardless of which decade you're currently fabulous in.