Wylder Hotels courts lifestyle, adventure seekers

TILGHMAN ISLAND, MD—If you’re looking for a lifestyle hotel in New York, Seattle or Nashville, TN, you can find one on just about any street corner. But authentic, experience-driven stays aren’t just for urban travelers—what about those unexpected, tertiary markets? Wylder Hotels, a new hospitality company, aims to fill that gap.

John Flannigan, founder/CEO of Wylder Hotels, said, “I felt like there was white space in smaller locations; Wylder is all about finding surprising locations with adventure attached, properties with soul that we can unlock, turn around and reimagine.”

Flannigan noted that while there are many one-off properties doing that really well, “there are very few scaling it in tertiary markets or surprising locations where there’s a huge need.”

And he should know. With more than 20 years of experience in the industry, Flannigan has led teams in acquiring, rebranding and operating hotels such as New York City’s Hotel Giraffe, The Roger New York, and Ace Hotel; and California’s Oceana Beach Club Hotel Santa Monica, Avalon Beverly Hills and Palm Springs, and Hollywood Proper. Now, he’s bringing that lifestyle aesthetic to smaller markets.

“We’d like to see Wylder hotels in locations like Northern California, Lake Tahoe, Montana, Middle America, upstate New York—locations that typically don’t have thoughtful, independent boutique hotels, but do have skiing, fishing, hiking, kayaking or things that get people to enjoy the wildness of the environment,” he said. 

First up? Wylder Hotel Tilghman Island here, which will open this month, marking the company’s portfolio debut. “Tilghman Island is pretty far out, but it’s only 90 minutes from DC or Baltimore. It’s incredibly beautiful, and it has great water access to the Chesapeake Bay,” Flannigan said.

He was introduced to the property by way of his best friend, a native to the island. “I fell in love with it,” he said. “I felt it had massive potential, and when it became available, I acquired it. It feels like a dream Wylder hotel.”

Built in the 1800s, the hotel was originally a boarding house, and then became the historic Harrison’s Chesapeake House, where many politicians engaged in fishing expeditions with its owner, Captain Levin F. “Buddy” Harrison III. “It’s got this incredible history,” Flannigan said, noting that, in the heart of Chesapeake Bay, the island is the epicenter of working watermen. 

But, unfortunately, the property fell into disrepair during the 2008 downturn, something Flannigan worked hard to rectify. 

“It took me a year to get it up to code and get it grandfathered nonconforming status, so that made the property very valuable because it can never be reproduced in terms of zoning regulations,” Flannigan said. “And I was acquiring it for significantly under replacement cost, so regardless of the real estate cycle, it made a lot of sense from a real estate standpoint.”

Wylder Hotels partnered with Revolver New York, a branding agency, to transform the property. With 54 newly designed guestrooms, the hotel will offer a relaxed seaside cottage vibe infused with modern comforts. Other amenities will include a new saltwater swimming pool; three food and beverage concepts, including two restaurants envisioned by Chef Sean Wheaton, a seven-year alum of José Andrés’ Think Food Group; 3,000 sq. ft. of meeting and event space; and 25 boat slips.

Redesigned grounds will further enhance the property. In addition to charter fishing, guests will be able to use stand-up paddleboards and kayaks or play bocce and other lawn games.  

Guestroom design calls for dark navy wainscoting and warm sisal carpet, and a clean palette of golden wood headboards, brass fixtures and woven rattan lounge chairs.

But, Flannigan noted, guests shouldn’t expect every Wylder hotel to feel the same as this one. When it comes to design, he said, “I’m excited about honoring what’s there, embracing the weirdness of what you may buy, and figuring out creatively how that can be turned to your advantage. So I don’t know if there will be a signature design element.”

Reflecting further, he added, “I think, generally, hotels are over-designed. I see the pack of brands so hyper focused on design, where good design is very smooth and you don’t notice it as much because you’re not trying so hard. You let the property and the location be the star as opposed to the fabric or the really expensive chair.”

Reinforcing the brand ethos—a hotel uncluttered by trends, brimming with distinct character and effortless sophistication—Flannigan said, “You’ve still got to do the basics well. Gimmicks don’t last and, at the end of the day, you need friendly people, a clean room and you need to deliver on expectations of service execution and food and beverage. If you don’t have [all of that], it doesn’t matter how cool you are or what your design looks like—you can’t be successful.”

According to the CEO, Wylder Hotels’ target customer is everybody. Flannigan explained, “Every human being likes the idea of adventure, likes the idea of going someplace that’s surprising, that catches them off guard in an interesting way. We expect to get senior citizens, families, millennials, locals, international travelers. We hope to be egalitarian in that way.”

In terms of growth, Flannigan said that he doesn’t want to grow too big, too fast. “One at a time is key—short term is carefully, without moving on until the first one is done really well,” he said. “When we’re happy with that one, then we’ll start looking at the next one. We don’t want to grow too fast where we miss what our core philosophies are—just having a great experience at a unique property. Long term, we certainly want to grow the brand 10 properties over the next 10 years, but we’re not under any pressure to grow other than organically at this point.” HB