Boutique Hotel Brand Wayfinder to Ride Experiential Hospitality Wave in Waikiki

When Phil Hospod started his hospitality firm, Dovetail + Co, back in 2018, he was coming off some pretty big wins as part of the Sydell Group, helping launch the Freehand New York and The Line DC. Still, he knew he wanted to go out on his own.

“It was more of a matter of when than if I started my own company,” said Hospod. “I wanted to do something personal and something for the long term, and I really see this as my forever business.”

Dovetail + Co’s latest property, Wayfinder Waikiki, will officially open at the end of May — just in time for the U.S. Memorial Day holiday. It’s a bigger gamble for the brand, considering it’s a larger property — with 228 rooms — and in a larger leisure market. 

The brand’s first location launched in Newport, Rhode Island, in 2020 with 197 rooms and a fresher, more playful take on traditional hotels in the area — which tend to feel stuffy, inspired by the town’s Gilded Age roots. Unfortunately, a fire broke out at the Newport hotel in the spring of 2022. The property is now under reconstruction, and Dovetail + Co. hopes the hotel will be able to “soft open” this summer.

Over in Waikiki, Hospod is hoping that a lack of boutique hotels with a quirky, relaxed vibe will enable his brand to stand out. He’s betting on “experiential hospitality,” or offering original experiences for guests rather than adhering to a big chain’s “brand standards” and “standard operating procedures.”

“It felt like we had an opportunity in Waikiki to lean into the playbook of boutique hospitality, and carve out our niche within the space,” said Hospod.

Winning in Waikiki?

Take a look at any image of Waikiki, and you can visibly see the hotel competition in the city. Even so, Hospod and his team saw a gap in the market. 

“When we looked at the Waikiki landscape, it really did feel like out of the tens of thousands of hotel rooms that are there, there really weren’t that many hotels that were trying to tell more interesting stories or provide more unique experiences,” Hospod said.

At the Wayfinder in Newport, Hospod created experiential programming that lets guests go a little deeper. He claims it resonated with guests.

“Yes, we’ll help guests play polo and sail in the bay, but we’ll also give you an inside look into an oyster farm and how you actually do oyster farming or cultivating sea salt,” Hospod said. 

Wayfinder Waikiki will follow a similar formula, only with experiences tailored to the island of Oahu. They expect guests will want to spend time on Waikiki’s beaches, but they also want to help them experience something unexpected. 

“Go to the Windward side of Oahu, and we’ll hook you up with a farm that does regeneration of taro patches, which is one of the keystone starches in the Hawaiian culinary tradition,” Hospod said. “You’ll talk about native Hawaiian history and culture and the importance of it, and why we’re only visitors here and why we need to tread lightly and with respect.” 

He’s also hoping the hotel’s retro-meets-updated design elements add to the guests’ experience. The building’s exterior, at first glance, seems imposing (and under other ownership, could have been a tear-down project), with its brutalist-style dating from 1969. But Hospod noticed that the architecture is “intentional,” with details like curves and fluting that add character.

“We decided to lean into it, and say, ‘let’s tell that story,’,” Hospod said.

Working with the Honolulu-based design firm The Vanguard Theory, they did attempt to soften the heavy exterior with bright colors and fabrics, natural woods, and plants — lots of plants. 

“Once you get the people in it, and the music, and the coffee, and the cocktails and the food, now all of a sudden, you’re like, ‘This is funky, I see what you guys did,” said Hospod. 

Speaking of music, in the lobby, guests will hear a playlist that a local record company, Aloha Got Soul, created for them.

“It’s this mix of soulful, funky, Hawaiian music that’s also mixed in with some modern interpretations of it, so guests are like, ‘Oh, that’s kind of cool,’” said Hospod. 

The aroma from the coffee shop in the lobby also sets the sensory tone, said Hospod. “It really gives you a sense that this is going to be fun, this is exciting.”

The hotel’s real selling point, though, is its pool. “When we first walked in we couldn’t believe it — it has this 70-foot tropical lagoon pool hidden behind the main tower, so it feels like you’re in your own tropical oasis, but you’re minutes away from Waikiki beach, the birthplace of surfing,” said Hospod.

Going all in on the “paradise vibe,” they created a hidden tropical speakeasy called Lost + Found, which guests must locate around a corner.

Spreading Its Wings

It’s no surprise that Hospod is working on expanding his Wayfinder brand. “We’re definitely trying to get more Wayfinders in the world,” said Hospod.

He currently has destinations like Southern California, Florida, the Pacific Northwest, and a few mountain towns on his radar.

But Dovetail + Co is also “spreading its wings” in other directions. In 2021 Dovetail + Co acquired Cambridge Beaches, an 86-room cottage-style resort in Bermuda, which underwent a full renovation with help from the designer Kellyann Hee — formerly of Soho House’s design team.

This April, and into the summer, the resort will be celebrating its centennial anniversary. And as Hospod looks to grow Dovetail + Co’s portfolio, he’s searching for more opportunities to find stand-alone resorts like Cambridge Beaches immersed in nature, which he calls “elemental luxury destination resorts.” 

“We’ve been looking at more properties within this space as well because we’ve seen how transportive it really is, and how it resonates with people in such a positive way,” Hospod said.

Dovetail + Co is doing partnerships, too. They partnered with Urban Cowboy to acquire and create the rustic, 28-room Urban Cowboy Lodge in the Catskills, New York, which opened in the spring of 2020.

Also, in 2021 Dovetail + Co purchased the historic 99-room St. James Hotel in San Diego (which originally opened in 1913), and partnered with the Palisociety to help turn it into the Palihotel San Diego, , which launches this May.

Whether it’s a partnership or solo project, Hospod’s goal with Dovetail + Co is to take on projects that excite him — and have fun with it. 

“That’s one of the beautiful things about our space in the independent boutique hospitality world is that we get to handcraft these physical environments as well as create our own ‘play,’ if you will, for each location and each property to surprise and delight our guests hopefully,” Hospod said.