From the moment you arrive at Dunedin, Florida’s Fenway Hotel, you feel as if you’ve stepped back in time. The massive lawn, brick walkways, and Mission styling evoke the 1920s. Most nights, live music—often from that era—spills from the lobby. I honestly wouldn’t have been surprised to see flappers smoking cigarettes in long holders as I entered.

And, yet, the hotel is completely modern with good Wi-Fi throughout and Alexa in every room. Need an extra blanket? Just call out, “Alexa, send an extra blanket,” and staff will bring a blanket. Unsure whether to bring a jacket? Ask, “Alexa, what’s the weather today?” You’ll get an answer.

Fenway Hotel

The Fenway Hotel at dawn. Photo courtesy of Fenway Hotel.

The Fenway Hotel is Full of History

It’s the history that really wowed me. Originally opened in 1927 in Dunedin—about a half hour from Tampa—the hotel welcomed the era’s top politicians, musicians, and celebrities including lawyer Clarence Darrow and Arctic explorer Robert A. Bartlett. It also hosted the county’s first radio station, WGHB, which is today WFLA.

Following the Depression and World War II, the hotel became a private club, operating seasonally until 1961 when it became Trinity College. After the college relocated in 1988, though, it sat empty for years. The city recognized its historical significance but wasn’t sure what to do with it.

Fenway Hotel Florida

Another view of the Fenway Hotel from the Caladesi Ballroom Patio. Photo courtesy of Fenway Hotel.

That’s when the Taoist Tai Chi Society of the USA purchased the hotel to use as its national headquarters, realized they couldn’t renovate the property on their own, and partnered with Mainsail Lodging & Development. The development company maintains the hotel, and the tai chi society uses a building behind the hotel for its headquarters.

Luxury at the Fenway Hotel

Opened in November 2018 as a member of Marriott’s prestigious Autograph Collection, the Fenway Hotel features 83 guest rooms and suites. The color palette in the rooms is subdued: white walls, curtains, and bedding with the occasional pop of color from a rose-colored chair or turquoise-hued sofa. A cymbal hung on my room’s wall, emblazoned with the hotel’s name.

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A king bedroom with an ocean view. Photo courtesy of Fenway Hotel.

Downstairs, the lobby has a Roaring 20s feel. Across from the reception desk, a bar mixes craft cocktails. Most of the day, the bar is fairly quiet, but at night, it’s filled with guests sipping their drinks and listening to live music. (Note: My room was directly above where the band played, and I could hear the music, which winds down at 10 p.m. on weekends.)

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The Fenway Hotel’s front desk. Photo courtesy of Fenway Hotel.

I stayed the week the hotel opened, and despite a few rough spots (no working icemaker on my floor, no comfortable place to work on my computer in my room and the music), I loved the feel of the hotel. For having only been open days, the staff was amazingly polished and attentive. I’m sure they’ve only improved (if that’s even possible).

HEW Parlor & Chophouse

The hotel has one restaurant, HEW Parlor & Chophouse, and its name is a play on words. “Hew” means to cut or chop, a nod to the restaurant’s focus on steaks and slabs of lamb, bison, and boar for dinner. But, it’s also the initials of the Fenway Hotel’s original architect, Herman Everett Wendell.

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The HEW Parlor & Chophouse. Photo courtesy of Fenway Hotel.

Inside, the décor is simple, and the breakfast, lunch, and dinner menus are fairly straightforward. For breakfast, try the Scottish option, featuring black pudding, tomato, and white beans, in honor of Dunedin’s city founders who hailed from Scotland. At lunch, choose from salads, soups, and sandwiches.

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The HEW specializes in steaks, chops, and fish. Photo courtesy of Fenway Hotel.

HEW is popular at dinnertime with locals, who come not only for the red meat options but also fresh fish. Save room for dessert. The goat cheese pannacotta is amazing!

Hi-Fi Rooftop Bar at the Fenway Hotel

Even if you don’t stay at the Fenway Hotel, watching the sunset from its rooftop bar is a must and one of the highlights of my visit. Arrive early enough to get a table on the far side of the bar, closest to the ocean. Even if you get there a bit later than planned, you can usually find a place to snap a few sunset selfies.

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Sunset from the Hi-Fi Rooftop Bar. Photo courtesy of Fenway Hotel.

As you wait for the sun to set, order a craft beer from local breweries, like Dunedin Brewery, the state’s oldest craft brewery. Or, sip a glass of wine or freshly-mixed cocktail.

Parents: You must be at least 21 to visit the rooftop bar. Head to the beach or a local restaurant with a view if you have kids.

Beyond the Fenway Hotel

The Fenway Hotel is ideally located just a few blocks from downtown Dunedin. You can easily walk downtown from the hotel in 15 minutes or hop on the Jolley Trolley. The trolley not only takes you to downtown Dunedin but also connects you to Clearwater Beach on one end and Tarpon Springs on the other.

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The Fenway is an easy walk to downtown Dunedin. Photo courtesy of Fenway Hotel.

In Dunedin, explore the souvenir shops, art galleries, and boutiques. Or, learn about the city’s history at the Dunedin History Museum. You can also rent bikes to ride the 38-mile Pinellas Trail. An offshoot from the trail takes you to Honeymoon Island State Park as well as the ferry to Caladesi Island State Park, ranked among the nation’s top 10 beaches for its white sands.

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Sample local craft beer at the Fenway Hotel or nearby breweries. Photo courtesy of Fenway Hotel.

After a day of shopping or outdoor recreation, quench your thirst at one of Dunedin’s breweries. Dunedin Brewery is always a good choice, but I also liked Woodwright Brewing Company, where you can sit outside around fire pits and listen to live music. Other breweries worth trying include Cueni Brewing Co., Caledonia Brewing and 7venth Sun Brewery. Your visit to The Fenway in Florida is sure to be filled with a few wow moments.


As is common in the travel industry, the writer was provided with accommodations, meals and other compensation for the purpose of review. While it has not influenced this review, the writer believes in full disclosure of all potential conflicts of interest.

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From the moment you arrive at Dunedin, Florida's Fenway Hotel, you feel as if you’ve stepped back in time. The massive lawn, brick walkways, and Mission styling evoke the 1920s. Most nights, live music—often from that era—spills from the lobby. #luxury #hotel #FenwayHotel #Florida #wowmoments

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