Best Historic Stays: Fenway Hotel in Dunedin

Known as “The Grand Lady of Dunedin,” the Fenway Hotel draws the eyes of those who pass by on Edgewater Drive. This picturesque hotel, built in 1924, is an icon of the jazz age. It has seen numerous transformations over the years, but now, as a member of the Autograph Collection, it’s hitting all the right notes!

History of Fenway Hotel

Fenway’s journey began in the roaring 1920s. While its name may evoke thoughts of Boston’s Fenway Park, General Manager Adam Duffey explains the name actually derives from the hotel’s surroundings at the time.

“‘Fen’ is another name for marshland, and when this hotel was being developed, there was a bit more marshland around, so they just took ‘Fen’ and added ‘way’ to it,” said Duffey.

In addition to being as a destination for vacationers, Fenway Hotel served as Pinellas County’s first radio station from 1925 to 1927. The WGHB Radio Station, sharing initials with the hotel's owner, G.H. Bowles, broadcasted from the rooftop, cementing the Fenway's place in broadcasting history.

Over the decades, the hotel transitioned through various phases, including stints as a private club, a minor league baseball team headquarters, and even a university. In 2018, the property reopened as the Fenway Hotel, part of the Marriott Autograph Collection, after a meticulous renovation by Mainsail Lodging & Development.

The hotel's history is proudly displayed throughout its halls. One spot that caught my eye is the door near the lobby that leads to Fenway’s original speakeasy. According to legend, you would knock three times and be asked for the password. If you said the right password, you could stop inside and enjoy a drink.

Staying at Fenway Hotel Today

Today, Fenway Hotel has 83 guest rooms and suites. Our Classic Queen, with two queen beds, had views that overlooked the magnificent entrance of the hotel and a partial view of St. Joseph Sound.

In addition to custom Fenway robes, you’ll find a well-stocked mini bar, mini-fridge, coffee maker, and modern bathroom with fantastic lighting, beautiful tiling, and a large shower. The nods to Fenway’s history continue with the gold record mounted on the wall.

Fenways has a range of amenities, including a resort-style pool, fitness center, and expansive lawn. Be sure to walk across the street to get close-up views of the beauty of St. Joseph Sound. You may just see a wading bird looking for a snack or a dolphin passing by.

Dining at Fenway Hotel

Fenway Hotel is home to HEW Parlor & Chophouse and Hi-Fi Rooftop Bar, both popular with visitors and locals alike. HEW is known for its seafood and steak, while Hi-Fi is one of the best places to grab a drink at sunset because of the panoramic views of St. Joseph Sound. And, get ready for the sound of symbols crashing as the sun goes down. It’s a Fenway sunset tradition!


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