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 three-story 10,000 square foot stucco building is appropriately on Edgewater Drive—since it faces the Intracoastal, St. Joseph Sound. 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 Tai Chi Society. In 2018, the property was re-imagined by Mainsail Lodging & Development as a boutique hotel and joined Marriott’s 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 83 rooms and suites.  They gave us a beautiful room with a king-size 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.

The hotel offers complimentary bikes for the first hour. Bikes are reserved via Zybra app and once the hour is up, your credit card is automatically billed.

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

The Pinellas Trail, a pedestrian and bike-friendly path, cuts right through town so this gave us a chance to ride some more. We rode through some high-end neighborhoods with friendly people 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 rooftop bar that offers some of the nicest sunset views in the area. At Hi-Fi Rooftop Bar, you can also see the big bridge to Clearwater, and views of the other barrier islands.

The bar was vibrant for Happy Hour, with dozens of people enjoying the ambiance and the pending sunset. 

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

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 not 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 around the corner to watch the singer perform some recognizable songs from the 70’s and 80’s.


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 our 90-minute drive.

An excellent relaxing trip at a unique destination–in our own backyard.  www.FenwayHotel.com

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