Fenway Hotel

Fenway Hotel: A place ‘humming with soul’

As a Travel Writer over the past 13 years, I’ve had a chance to see some beautiful resorts—but the assignments I enjoy the most are not always the ones in major cities with well-known places.  Nope, I have an affection for charming hotels in small towns with active “Main Streets” where we can immerse ourselves into the community for a couple of days.

Fenway Hotel has been called “The Grand Lady of Dunedin,” near Clearwater. It has also been called “The most historically valuable structure in Dunedin.”  The 3-story 10,000 square foot stucco building is appropriately on Edgewater Drive—since it faces the intracoastal. It has a large front lawn and center entrance under a portico.

Originally opened in 1927, it has been home to a radio station (“the region’s first”), a private club, a university and most recently home to the Taoist Tay Chi Society! In 2018, the hotel was re-born as part of the Marriott Autograph Collection.

Fenway Hotel plays off its early roots in radio and has a music theme throughout. There is live music each night, and the front desk clerk answers the phone, “Broadcasting live from Fenway Hotel.”  Their catch phrase is “Fenway Hotel—a place humming with soul.”  Unique angle.

Erin and I checked in to one of the eighty-three rooms.  They gave us a beautiful room with a King-sized bed facing the water.  The bathroom had a glassed-in shower and the vanity had plenty of space. Perfect.

After unpacking, we went back downstairs to explore Dunedin.

To use the hotel’s bikes, you first must download an app, insert your credit card information and you’ll be billed if you stay out longer than an hour.

We headed north toward the downtown area to explore Main Street.  We ate, shopped and people-watched on Main Street.

The Pinellas Trail, or bike-path, cuts right through town so this gave us a chance to ride some more. We peddled through some high-end neighborhoods with friendly residents waving from the porch.  We also stumbled upon the Toronto Blue Jays Spring training stadium. 

By the way, even though the hotel is named “Fenway,” it has nothing to do with iconic Fenway Park in Boston where the Red Sox play.  Etymologists say “fen” means “marshland” which apparently was prevalent in the 1920s when the hotel was first named.


Fenway Hotel has a roof-top bar that offers some of the nicest sunset views in the area. You can also see the big bridge to Clearwater, and views of the other barrier islands. They call it the “Hi-Fi Rooftop Bar” and they gave us two drink tickets with our key when we checked in. The bar was crowded for Happy Hour, with dozens of people enjoying the ambiance and the pending sunset. 

Fenway Hotel

Dinner was a nice surprise.  The restaurant is called the “HEW Parlor & Chophouse.” (“HEW is the initials of the architect, Herman Everett Wendell.)  There’s a brightly-lit restaurant, as well as a charming “parlor bar” in the lobby, more seating along the swimming pool—and more tables available on the front porch–and that’s where we chose to dine.

It was a pleasant evening, great service and fun watching other hotel guests arriving with their luggage. A singer was also outside, just far enough to be heard but never overwhelming.

Erin had the Cast Iron-Seared Jumbo Scallops and I had a 10-ounce filet.  We split Yukon Gold Whipped Potatoes, Steakhouse Mushrooms and Roasted Brussels Sprouts.  Delicious!

We stayed for a nightcap and went over to watch the singer perform some recognizable songs from the 70’s and 80’s. Just a beautiful night overall.

Fenway Hotel

We had good intentions of waking up early and hitting the bike path, but we instead lazily enjoyed the morning and found our way down to brunch.  Creatures of habit, we sat in the same two chairs as 12-hours earlier!

The omelets were excellent, as well as the hot coffee and cold orange juice.  It was also nice to meet the General Manager, Mickey Melendez, who made the rounds checking on the diners.  Nice touch.

After brunch, we packed up, headed back downstairs, enjoyed a 5-star Valet Parking attendant named Jose and drove south on US 19 back to Sarasota for a 90-minute drive.

An excellent relaxing trip at a unique destination–in our own backyard.  Fenway Hotel website.

Ray Collins is a Realtor, elected official, media consultant and travel writer.  To see other articles, go to HERE.

Photos from Ray Collins

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