5 Most Underrated Cities in the USA, According to Ash Hotels' Ari S. Heckman
A hotelier who builds in off-the-beaten-path cities, shares his top five
This winter we’re starting a new rhythm in Escape Club: every other week, we ask someone with real experience or insight to share a quick “Top 5” from their world — design, hospitality, food, nature, and the quieter corners of culture that shape how we travel. It’s a chance to hear directly from people who actually live and breathe these places, and a small bonus for our paid subscribers.
We kicked off the series with Casey Scieszka — writer, innkeeper, and co-owner of Spruceton Inn — who shared her Top 5 motels across the U.S., drawing from years spent restoring, running, and reimagining one herself. In the second, Tom Roberts of Homestedt and North Branch Cider Mill shared his Top 5 Most Charming Shops in the U.S.. Our third installment featured a personal list from Erin Lindsey, founder of EB: Top 5 Spa Resets I Took in 2025.
For this installment, we turned to Ari Heckman, co-founder and CEO of Ash Hotels, to weigh in on the most underrated cities in the U.S.
Ask An Expert: 5 Most Underrated Cities in the USA, According to Ash Hotels’ Ari S. Heckman
Ash Hotels has built its reputation by doing the opposite of what most hospitality brands chase.
Instead of obvious destinations or easy luxury, the team gravitates toward cities with cultural depth, architectural history, and a sense of place that hasn’t been overly polished for mass tourism.
Founded by Ari S. Heckman, Ash is known for transforming historic buildings into immersive, design-forward hotels that feel rooted rather than imposed. Properties like Hotel Peter & Paul in New Orleans, The Siren in Detroit, and Hotel Ulysses in Baltimore are less about spectacle and more about atmosphere — layered, cinematic, and deeply contextual.
That sensibility extends beyond design. Ash develops, owns, and operates its hotels, shaping everything from furniture and lighting to food programs, music, and printed ephemera. The result is a cohesive experience that feels intentional without being precious.
Just as important is where Ash chooses to build. Many of its properties sit in cities that reward curiosity — places with strong local scenes, diverse communities, and creative ecosystems that don’t rely on constant validation from trend cycles.
Which makes Ari a natural fit for this list. His picks reflect a long-standing interest in cities that are working, evolving, and culturally rich — places that don’t need rebranding, just closer attention.
Below are Ari’s picks, along with three of his favorite spots in each — spanning food, vintage, outdoors and art — from one of the tastemakers shaping today’s hospitality landscape. We’re sharing it exclusively with our cherished paid Escape Club members.
I’ve personally spent time in just one of these cities — Tucson — but it’s a place I liked so much that I returned to, and can confirm it belongs firmly on any list of underrated American cities. Ari nails what makes it special: the light, the landscape, the vintage scene, and the food. The Tohono Chul Botanical Gardens, hike up Sentinel Peak, and an easy day trip up to Mt. Lemmon only deepen the case.
Now that we’ve given one away (I couldn’t resist), below, find the four others.
Enjoy,
-Erin + the EB team