The Fenway Hotel is Composed Luxury on the Coast

One of the joys of living in Florida is discovering a new-to-you town with the kind of down-home ease and coastal quirks that only exist in the Sunshine State. One such place is Dunedin, nestled along the Gulf Coast just 30 minutes west of Tampa. Here, visitors will find a supremely walkable downtown dotted with locally owned restaurants, breweries, and shops, plus beautiful beaches and plentiful recreational activities. Best of all, Dunedin is home to a historic hotel with modern bravado: the Fenway Hotel.

The Fenway has undergone many iterations since first opening as a hotel nearly a century ago. In its earliest years, it hosted icons of the Jazz Age, including notable artists and musicians. Echoes of that original era are present in the Fenway of today, which re-debuted as a hotel in 2018 and is now a member of Marriott’s Autograph Collection.

A prime example of Mediterranean Revival architecture, the Fenway is suffused with hints of its 1920s grandeur, most notably through its musical references. A lobby stage is set against a backdrop of instruments, while the 83 guest rooms and suites feature nightstands inspired by traveling musicians’ trunks, among other vintage details and subtle Spanish elements.

Hospitality at the Fenway also nods to the 1920s, with curated dining concepts and experiences that feel refreshingly analog. Take Room 27, for example. Hidden next to the hotel’s main restaurant, this speakeasy lounge is accessible only after you provide a password to a bartender at the lobby bar. Once inside, guests sip Prohibition-era cocktails and soak in a space that feels worlds away and years removed from 2026.

When hunger hits, head to HEW Parlor & Chophouse. A play on both the word “hew” and the initials of the hotel’s original architect, Herman Everett Wendell, HEW puts a chef-driven spin on traditional steak house fare, complete with an open kitchen and a large chef’s counter. Seafood, seasonality, and the South strongly influence the menu, as evidenced by the craveable seafood beignets and divine local sides (don’t pass on the crispy brussels sprouts). The steak program is equally impressive, with luxe offerings like Japanese A5 filets, the perfect base for HEW’s creamy Japanese Bordelaise. Return to HEW Sunday mornings for brunch with a side of live jazz.

One of the Fenway’s greatest strengths is its location. Its Hi-Fi Rooftop Bar boasts gorgeous waterfront views of St. Joseph Sound. Two blocks in the other direction is the Pinellas Bike Trail, so grab a complimentary bike from Fenway and start exploring. For those who prefer to wander on foot, Dunedin’s charming downtown is just a short stroll away. Browse shops like Back in the Day Books and Lead Lines Stained Glass Studio, or simply walk around and soak in the scene. However you choose to spend your day in Dunedin, the Fenway will be waiting to welcome you home. 

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