How One Hospitality Group Is Reviving Classic Hotels in Beloved Summer Destinations

Opening one hotel in a prime summertime market at the start of the season is a huge undertaking. Opening four in the span of just a few months is downright crazy.

But that’s what Blue Flag Capital, a Boston-based hospitality investment company that transforms historic or dated but beloved hotels, is doing this summer, expanding its portfolio from 6 properties to 10. “I wouldn’t say we like to do hard things,” says CEO and cofounder Jason Brown. “We just choose to do hard things every single time.” Chief design officer and cofounder Brad Guidi corrects him with a laugh: “I think we like to do hard things.”

The first of these new undertakings is Hotel Corduroy, which opened May 8 in Montauk, New York. In June, it will welcome Faraway Sag Harbor in New York and Faraway Jackson Hole in Wyoming; Oyster Estate in Greenport, New York on Long Island’s North Fork, will join the trio later this summer. They join two other Faraway properties, in Nantucket and Martha’s Vineyard, as well as four standalone hotels in Nantucket.

Brown says simply expanding the brand isn’t the point. They choose destinations that hold personal meaning to them, and with each hotel aim to honor the history and spirit of the place rather than stand apart from it. “We start with that sense of place, and we’re interested in all of the stories we can tell in these amazing markets, but we want to do it in this kind of magical way,” he says. “I think all hospitality—whether you’re talking about a hotel or restaurant or cocktail lounge, or fill-in-the-blank—is supposed to transport you out of your everyday life and bring you somewhere else.”

Courtesy of Oyster Estate

Storytelling is at the heart of each Blue Flag property. Before they begin work on a new hotel, Brown and Guidi craft a fantastical tale, always with a heroine at the center, that captures the heart and vibe of the destination. Faraway Sag Harbor’s, for example, follows a pearl diver who fell in love with Italy on her travels and decides to pay homage to the Amalfi Coast when she returns home. Faraway Jackson Hole’s heroine, meanwhile, is a horse whisperer.

Guidi says they think of each opening (and the seasonal reopenings) as if they’re putting on a Broadway show. “At the start of every season, we say, ‘Guys, this is a three-month run: You have to get the costumes right, the lighting right, the music right,’” he says. “They’re shows, they’re a performance every night, and we truly approach hospitality like theater.”

Like any good show, each hotel is totally unique. Blue Flag works with different design teams to fully create a sense of place that matches the destination (masonry fireplaces and distressed leather sofas in Jackson Hole, glass cloth wallpaper and midcentury-modern furnishings in Montauk); they even craft a specific scent for each property.

Here’s a quick look at each of Blue Flag’s new properties:

Hotel Corduroy: Montauk, New York

Photos by Matt Kisiday

Located just steps from a private beach in Montauk, the 29-room Hotel Corduroy was built in 1983 and reimagines the classic surf motel for today’s traveler, blending contemporary design with an easy, nostalgic nod to 1980s surf culture (think: a curated cassette library with everything from Elvis Presley to Jimmy Buffett). Guidi and Brown are especially excited about the central lawn, which has firepits and sun loungers, beach chairs, and umbrellas from California-based Business & Pleasure Co., known for its dreamy, retro-striped beach furniture. “It’s going to be the heartbeat of this property,” says Guidi. “It just feels so Montauk.”

Faraway Sag Harbor: Sag Harbor, New York

Set along Sag Harbor cove, the 67-room Faraway Sag Harbor (opening June 4) unfolds like a coastal estate, weaving together the village’s maritime and whaling heritage with a more transportive, Mediterranean sensibility. Originally opened in 1958 as the Sag Harbor Motel and Inn, it quickly became the place to see and be seen for hobnobbing with celebrity creatives like Paul Newman and Jackson Pollock. Today, guests will be encouraged to drift between a series of interconnected spaces—from a ground-floor bar and lounge to the pool terrace and up to Zagara, the hotel’s Amalfi Coast–inspired restaurant overlooking the harbor. “The transition from day to night there is magical,” says Brown.

Faraway Jackson Hole: Jackson Hole, Wyoming

Courtesy of Faraway Hotels

Blue Flag’s first noncoastal property, Faraway Jackson Hole (opening June 10) is a total transformation of Teton Village’s Snake River Lodge, which was originally built in 1968. While some of that property’s elements were preserved, such as its vintage elevators, it feels entirely new, with a theatrical western-inspired decor that leans into Jackson’s roots. A basecamp for year-round adventure, there are 90 rooms and suites and 48 residences; a restaurant, Sure Hand, offering craft cocktails and seasonal fare; and an indoor-outdoor pool, hot tub, and sauna that Brown says “will be a pleasant surprise for everyone.” (Blue Flag also acquired neighboring Alpenhof Lodge, which will 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 a more design-forward sensibility to the North Fork, drawing inspiration from the area’s working harbor as well as its surrounding farms and vineyards. Guidi says it was important to “tap into” what was already there. “The first thing we do is look around and say, ‘All right, where are we?’” he says. “It’s not our job to impose our own aesthetic.” The hotel is anchored by a newly built courtyard pool and patio and will also feature a cocktail bar and restaurant, Fortune Favors, inspired by Japanese listening lounges, where a carefully considered sound system will shape the experience as much as the menu.