Fenway Hotel, Autograph Collection

Dunedin's Grand Lady on St. Joseph Sound

★★★★★📍 Dunedin waterfront (St. Joseph Sound)$$$

The Fenway opened in 1927 as a seasonal hotel for well-to-do winter visitors, and its story is better than most. In 1925 the site was home to WGHB, the first radio station in Pinellas County, broadcasting from the roof; during Prohibition a speakeasy operated on the ground floor, and its preserved entrance is now on display in the lobby. The hotel closed in 1961 and went through lives as a college campus and, later, a graffiti-covered shell with squatters, coming close to demolition more than once. The Taoist Tai Chi Society of the USA bought the property in 2014, partnered with Tampa-based Mainsail Lodging and Development, kept the exterior intact and gutted the interior; the hotel reopened in late 2018, and Tai Chi on the lawn remains part of its program.

Room craft: the 83 rooms are of average size for a 1920s building, with a playful music theme and either two queens or one king; suites roughly double the space and add a separate living room. Bathrooms are shower-only, and a single guest elevator serves the building, so allow extra time or take the stairs. Request a room facing the sound for sunset views. Reserve dinner at HEW on weekends (it has an open kitchen and a prime-beef focus, plus seafood and vegetarian options), take breakfast on the front veranda, and go up to the rooftop before sunset to get a seat, since Hi-Fi is open to the public and fills fast. Bikes are available for the ride downtown and along the Pinellas Trail, and the lawn has croquet, bocce and cornhole.

Practicals: 453 Edgewater Dr., Dunedin; about 30 minutes from Clearwater Beach traffic permitting and around 40 from Tampa International, with no airport shuttle. Parking is valet only for a daily fee, pets are not allowed, and the minimum check-in age is 21. How it compares: if you want sand at the door, Clearwater Beach resorts such as Opal Sands are the better fit; the Fenway trades that for history, a walkable small town and the islands. Fit: couples, history lovers and travelers who want Honeymoon and Caladesi Islands on their doorstep. Less suited to families with young children who need a beachfront pool scene.