Crew's Quarters Boarding House: Affordable Ptown Lodgings with a 'Bad Boy Sailor's' Vibe

Throughout the process Jackson was well aware of his business model, that of a budget hotel based on a limited number of rooms. Add to this a commitment to providing an affordable space for younger visitors in a town where they are increasingly being priced out by rising costs.

"I learned from being a queer activist from my youth that ensuring and maintaining inclusion and diversity is really important to me. So, when I created this place, I wanted to be like one of those born good entities. And maintaining the price points where they are really provides economic diversity and access to people. I have younger folk that come in who may not be having the biggest, fattest wallet, but they still want to stay in Ptown. The lower price point gives them the opportunity. I did not want to create a model or an inn that would be exclusive to people based on money. You can stay here on the shoulder season in our cheapest rooms for like $100 to $120. Or during our peak weeks (Bear Week and Carnival) when the same rooms are about $240 when other places around town are charging $500 to $700 a night. We are intentionally operating at that lower quartile so people can come in and stay here."

"But," he adds, "the contradiction that I'm giving our clientele is that we provide a lush, curated experience that represents my brand. I'm really trying to deliver cheap chic within the speakeasy queer vibe. So I wanted to offer access, but I also wanted to offer a really unique, quality experience at the same time. You are just not coming to a budget hotel, you are coming to one of the best in town."

Jackson is presently in the process of expanding that number with renovations that will begin in September. In addition to adding two rooms, he will be able to add central air, relocate the deck, make his space ADA compliable, and expand the footprint of his lobby and bar. "I love the sweaty moments that are created by having no AC. But we're getting hotter as a planet, and people are used to air conditioning as a norm."

One trend that Jackson has happily embraced is that of Crew's Quarters Boarding House becoming Ptown's latest social space. In a time when socializing is hooking up on Sniffies, he has seen his bar become a great place for some old school socializing, the bar and patio packed during the season with those looking for a spot between TDance and late night activities. To enhance the experience, and to the enjoyment of many, Jackson projects movies onto the white wall of an adjacent building, so don't be surprised to see Marlon Brando or Tab Hunter larger-than-life while enjoying a cocktail.

"The bar is a central spot for people to connect. And I think it's a bit different than going to even just a bar, because this is so much more intimate," he says. "The way people connect today is through hookup apps. It is the way young people, and most people, connect. And they're great if you want to pick someone up, but as a way of just connecting on a more personal level, they can be limiting. So when they come in here, they realize that it's sort of like an analog experience that has some history to it. They're stimulated, motivated, turned on by it. They, they love it."

If anything, what Jackson is doing is bringing a Club Cumming vibe to Provincetown (Club Cumming is the East Village club run by actor Alan Cumming, where he hangs out when he can). A welcoming social space with a masculine edge, that is. "I am creating what would have been around for us in the decades before Stonewall. My idea is to recreate the bad boy sailors' tavern at the end of the jetty, but also bring a bit of urban cool into the middle of picture perfect Cape Cod. I am very much focused on creating a story and protecting a legacy, and I wanted to provide to the guests an experience that I don't think they have been offered in a gay context before. I'm keeping a gay legacy alive here, and I'm providing something that is more than just a nylon flag from Amazon."

And as for painting his residence black, Jackson has received some validation in a town where cookie-cutter Cape Cod vistas prevail. "I recently spoke to my contractor, who said to me that they've gotten five requests for the Crew's Quarters Boarding House treatment. So you see little black houses popping up around town now."

Check out the Crew's Quarters Boarding House's website for more.

Also visit its Instagram for a curated visit to the queer past that the Rooming House evokes.