Return to Glory at the Fenway Hotel in Dunedin, Florida

When we first got a look at the Fenway Hotel in Tampa Bay, it was at the property’s opening day party. We got into this revitalized Dunedin hotel the same day the local mayor, the developer, and the tourism director were doing a ribbon-cutting ceremony and throwing open the doors. So we wanted to spend the night there a few years later to see how things were coming along.

The Fenway Hotel opened in 1927, despite there not being a whole heck of a lot of people on the Gulf Coast of Florida then, much of the area more occupied by orange groves than people. This was long before there were fancy Clearwater resorts on the barrier island nearby. It was a grand affair then that attracted high society, not least because of the speakeasy barely hidden on the ground floor. It was a jazzy joint, a place filled with music. It also housed the county’s first radio station, launched in 1925. (The “do not disturb” signs here say “Off Air.”)

It operated seasonally as a hotel through 1961. Then the building went through many lives, including several colleges, but also a squatter site. Several times it came close to demolition and an empty lot.

In 2014 a savior came along and bought the abandoned building and land. The non-profit Taoist Tai Chi Society of the USA wanted it to become its new national headquarters and a new international center for its parent society. As they went through various approval processes, it became clear that making it a boutique-sized hotel again was going to keep the regional stakeholders happy and serve the society as well—with their less ambitious set of community townhouses in the back for the Taoists. They packed it out with member bookings to kick things off.

Unlike with beach hotels that are crammed in next to each other in nearby Clearwater Beach, there’s plenty of room to breathe at this waterfront property. Lawns and palm trees are on three sides, then in a courtyard area in the back, there’s a long rectangular pool with lounge chairs and some shade much of the day on one side or the other. There are a few living room-like sitting areas under the palms.

Sometimes the expansive green space out front brings guests back to a more genteel time without addictive screens, with croquet, bocce ball, cornhole, or badminton on the expansive lawn. The Fenway is near one of the greatest rail-to-trail projects in the USA too, a 40-mile paved run that goes all the way down to St. Petersburg in the south and past Tarpon Springs in the north, all flat and off-road. There are also more than 20 craft beer breweries along the Pinellas Trail.

Fenway Hotel Dining and Drinking

The HEW Parlor & Chophouse is the main restaurant on site for this 80-room hotel, with an open kitchen, plenty of natural light, and a few hints of the retro vibe. The name is a nod to the original building architect Herman Everett Wendell. It has a range of seating indoors and out, including banquettes and seats along a bar that faces the open kitchen. As indicated by the name, there’s a sizable section of the menu devoted to prime cuts of beef. If you’re feeling hungry you can get a 40-ounce tomahawk ribeye steak with mushrooms, but there are nice salads, fresh seafood dishes, some great burgers, and a vegan “butternut squash steak” served up as well.

With spacing restraints in place when I visited in 2021, the restaurant had expanded onto the outdoor front veranda area of the hotel, which is a nice spot for breakfast even in summer months. Everything I sampled here was excellent and it was comforting to see it come straight from the kitchen when I sat at the bar facing where everything was prepared. See all three meal menus here.

There are 8 breweries in small Dunedin, and close to 70 now in Tampa Bay, so the Hi-Fi Rooftop Bar gets props for staying local with the tap selection and not selling out to the mass brewer distributor pressure. Despite all the good beer and cocktail lounges around the area though, this outdoor rooftop bar became an instant success with outsiders as well as guests: it’s one of the few places north of Clearwater Beach where you can look out at the Gulf of Mexico while having a drink. Here’s what the view is often like at sunset:

You won’t have to guess when the ideal time to grab a seat will be: your room key folder has the local sunset time marked. The hi-fi Bar is a breezy, shaded, attractive space that is great for socializing while watching the sailboats go by. There are around a dozen menu items you can order up here as well, shareables, sandwiches, and salads. Access is via the lobby elevator or directly by climbing 51 steps from the parking level.

There’s another bar in the lobby, where a jazz band will often be playing. You can belly up to the bar there or take a lounge seat in one of the sitting areas. As with the roof bar, you can find some local craft beers on tap or order a classic cocktail that’s been around since the ’20s.

There’s also a long list of good restaurants and bars in downtown Dunedin as well, which is close enough to walk or a five-minute ride away on the complimentary hotel cruiser bikes. You could even ride to see the local minor league baseball team play from here or ride about 30 minutes and spread a towel out on Honeymoon Island, which is a state park with beaches. The Fenway also has a gym on site for closer exercise options.

Fenway Hotel Rooms and Suites in Dunedin, FL

Rooms are of average size, and baths are shower-only, but The Fenway Hotel makes up for it with good design, modern touches, and a few musical cues. Two queens or one king bed with padded leather headboard sit on carpet and are surrounded by light color tones and dark stained wood. The conventional layout has a long row of counters and cabinets opposite the bed, with a wall-mounted TV, better-than-average minibar, and closet with Florida-appropriate cotton bathrobes.

It’s not the 1920s when it comes to electricity: charging units beside the beds have two regular outlets and two USB outlets, plus most lamps have more. A customized Alexa Dot unit functions as a music speaker, news broadcaster, and tourist information source. The attractive baths with an array of Spanish tiles have built-in toiletry dispensers in the shower

Each room has some kind of a musical touch, like a shiny cymbal on the wall with the Fenway logo. Suites have double the space, with a separate living room.

The Fenway Hotel is run by the Mainsail Properties group, the company behind several Florida properties including Epicurean Hotel in Tampa. Like the latter, it is part of Marriott’s Autograph Collection, which means you can cash in points to stay here or earn points to add to your loyalty account. The Autograph brand is Marriott’s “sense of place” one though, each hotel having its own personality, so you won’t see a lot of corporate reminders here.

The property meets ADA standards for accessibility, with wheelchair elevators to the check-in level and to the roof deck, but there’s only one guest elevator serving the entire building—leave a little extra time for getting to and from your room or use the stairs if you’re able.

Rates run $175 to $360 per night most of the time, with no sneaky fee add-ons besides local taxes. (If you bring a car, it’s $15 a night for valet parking.) See more details at Marriott’s Autograph Collection site and check rates there, at Expedia, or at Hotels.com.

Review and photos by editor Tim Leffel, who was a guest at the Fenway Hotel in Dunedin for purposes of review. As always, all opinions are his own.