The Fenway Hotel is the most characterful place to stay in north Pinellas and the ideal base for this site's northern islands. Opened in 1927 on the bluff above St. Joseph Sound in Dunedin, it hosted musicians, politicians and athletes in its heyday before falling into disrepair in the 2000s; a top-to-bottom restoration brought it back in 2018 as part of Marriott's Autograph Collection, with 83 guest rooms that mix period character and modern comfort. The public spaces are the draw: the Hi-Fi Rooftop Bar looks west over the sound toward the islands and is one of the best sunset perches in the county, HEW Parlor and Chophouse serves chef-driven dinners with a long whiskey list, the Parlor Bar handles cocktails, and live music in the lobby and lawn games such as croquet give the place a relaxed, sociable feel. An outdoor pool sits on the grounds. Downtown Dunedin — a walkable, independent small town known for craft breweries, a Scottish heritage and the Pinellas Trail — is a short stroll away, and Honeymoon Island State Park, the launch point for the Caladesi ferry, is only a few minutes' drive across the causeway. Fit: couples looking for a historic boutique stay, travelers who prefer a small town to a resort strip, and history lovers who want a hotel with a story.
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.
Why stay here
- ✓Restored 1927 historic hotel
- ✓Hi-Fi Rooftop Bar over St. Joseph Sound
- ✓HEW Parlor and Chophouse
- ✓Parlor Bar with live lobby music
- ✓Outdoor pool
- ✓Lawn games and Tai Chi on the lawn
- ✓Walk to downtown Dunedin
- ✓Minutes to Honeymoon Island
Good questions
How old is the Fenway Hotel?+
It opened in 1927, closed as a hotel in 1961, and was restored and reopened in late 2018 as part of Marriott's Autograph Collection after decades of decline. The lobby displays pieces of its history, including the old speakeasy entrance.
How close is it to Honeymoon and Caladesi Islands?+
Very close. Honeymoon Island State Park, where the Caladesi ferry departs, is a few minutes' drive across the Dunedin Causeway, and the Hi-Fi rooftop bar looks straight out toward both islands.
Is it on the beach?+
No. It overlooks St. Joseph Sound from Dunedin's waterfront and has an outdoor pool. The nearest beaches are on Honeymoon Island, minutes away by car.
