Opening a hotel in a major summer market early in the season is a big undertaking. Four openings in just a few months is just crazy.
But that’s exactly what Blue Flag Capital, a Boston-based hospitality investment firm that renovates historic and beloved hotels, is expanding its portfolio from six to 10. “We don’t want to do anything difficult,” says CEO and co-founder Jason Brown. “We just choose to do the hard thing every time,” chief design officer and co-founder Brad Guidi corrects him with a laugh. “I think we like to do difficult things.”
The first of these new initiatives is Hotel Corduroy, which opened on May 8th in Montauk, New York. In June, they will visit Faraway Sag Harbor in New York and Faraway Jackson Hole in Wyoming. Oyster Estates, located on Long Island’s North Fork in Greenport, New York, will join the trio later this summer. They join two other Faraway hotels on Nantucket and Martha’s Vineyard, as well as four separate hotels on Nantucket.
Brown says it’s not just about expanding the brand. They choose destinations that have personal meaning to them, and each hotel aims to respect the history and spirit of the location rather than be independent of it. “We’re interested in starting with the sense of place and all the stories that are told in these amazing markets, but we want to do that in such a magical way,” he says. “Whether it’s a hotel, restaurant, cocktail lounge or fill-in-the-blank, all hospitality is supposed to take you out of your everyday life and into another place.”
Storytelling is at the heart of each Blue Flag property. Before starting construction on a new hotel, Brown and Guidi craft a fantastical story that captures the heart and atmosphere of the destination, always centered around a heroine. “Faraway Sag Harbor,” for example, follows a pearl diver who falls in love with Italy while traveling and decides to pay homage to the Amalfi Coast when he returns home. On the other hand, the heroine of “Faraway Jackson Hole” is a horse whisperer.
Guidi said he thinks of each opening (and seasonal reopenings) as if he were putting on a Broadway show. “At the beginning of every season, we say, ‘Guys, this is a three-month run. We need to get the costumes right, the lights right, the music right,'” he says. “They’re a show, a nightly performance, and we’re really into theatrical hospitality.”
Like any good show, each hotel is completely unique. Blue Flag works with a variety of design teams to create the perfect place feel to match your destination (stone fireplaces and distressed leather sofas in Jackson Hole, glass cloth wallpaper and mid-century modern furniture in Montauk). They even create specific scents tailored to each establishment.
Here’s a quick introduction to each of Blue Flag’s new properties.
Hotel Corduroy: Montauk, New York
Located steps from Montauk’s private beach, the 29-room Hotel Corduroy was built in 1983 to reimagine the classic surf motel for today’s traveler, blending contemporary design with a nostalgic, familiar feel to 1980s surf culture (think: a curated cassette library of everything from Elvis Presley to Jimmy Buffett). Guidi and Brown are particularly excited about the center lawn. There you’ll find fire pits, sun loungers, beach chairs and umbrellas from California-based Business & Pleasure, known for its dreamy retro striped beach furniture. “It’s going to be the heart of this facility,” Guidi says. “It feels very Montauk.”
Faraway Sag Harbor: Sag Harbor, New York
Located along Sag Harbor’s cove, the 67-room Faraway Sag Harbor (opening June 4) unfolds like a coastal mansion, weaving the village’s maritime and whaling traditions with a more transportive Mediterranean sensibility. Originally opened in 1958 as the Sag Harbor Motel and Inn, it quickly became a meeting place for celebrity creatives such as Paul Newman and Jackson Pollock. Guests are now encouraged to move through a series of interconnected spaces, from the ground floor bar and lounge to the pool terrace and the hotel’s Amalfi Coast-inspired restaurant, Zagara, overlooking the harbour. “The transition from day to night there is magical,” Brown says.
Jackson Hole Far Away: Jackson Hole, Wyoming
Blue Flag’s first non-shore property, Faraway Jackson Hole (opening June 10), is a completely renovated 1968 Snake River Lodge in Teton Village. While some elements of that property have been preserved, such as the vintage elevator, it feels entirely new, with a theatrical Western-style décor that leans toward Jackson’s roots. A year-round adventure basecamp with 90 rooms and suites and 48 residences. Sure Hand is a restaurant that serves craft cocktails and seasonal cuisine. There will also be indoor and outdoor pools, a hot tub and a sauna, which Brown says will be a “pleasant surprise for everyone.” (Blue Flag also acquired the adjacent Alpenhof Lodge, which is scheduled to reopen in 2028.)
Oyster Estate: Greenport, New York
Opening in late summer in the heart of Greenport Village, Oyster Estate is a reimagined 34-room boutique that brings more design to the North Fork, drawing inspiration from the region’s working harbor and surrounding farms and vineyards. Guidi says it’s important to “leverage” what already exists. “The first thing we do is look around and say, ‘Okay, where am I?'” he says. “It’s not our job to impose our own aesthetic.” The hotel will center around a newly built courtyard pool and patio, and will also include Fortune Favors, a cocktail bar and restaurant inspired by Japanese listening lounges, with a carefully considered sound system shaping the experience as much as the menu.