There are hotels you stay at because they’re convenient, and then there are hotels that somehow become part of the trip. The Fenway Hotel in Dunedin was definitely the second kind.
We booked it because we wanted to stay somewhere close to downtown, somewhere with some personality, and preferably somewhere that didn’t feel like every other hotel we’ve stayed in. What we got was a historic hotel overlooking St. Joseph Sound, live music downstairs, steaks and martinis at HEW, a rooftop bar, a pool we eventually remembered to use, and one of the best Florida sunsets we’ve seen in a while.
Not bad for a place we originally thought would mostly just be where we slept.
The Fenway Has Been Doing This for a Long Time
The Fenway isn’t a new hotel trying really hard to look old. It actually is old.
The hotel traces its roots to the 1920s Jazz Age, and today it operates as part of Marriott’s Autograph Collection. The property still leans heavily into that musical history, from the décor and live music to the names of the restaurants and bars.
Even the hotel’s history gets a little confusing depending on what source you’re looking at. Regional tourism material dates the building to 1924, while some of the historical material we saw on-site discusses the Fenway becoming Dunedin’s major resort later in the decade. Rather than pretending I can settle a century-old date argument from my laptop, the important part is this: the Fenway was part of Dunedin’s early resort era and became one of the places where people gathered, ate, drank and listened to music.
The hotel also had a connection to early radio in Pinellas County. Fenway’s own material says the rooftop area was once home to WGHB, an early local radio station, and the hotel continues to play up that broadcasting and musical history today.
What I liked is that none of this feels locked away behind a velvet rope. The history is everywhere — old photographs, newspaper clippings, musical references, a cymbal bearing the Fenway name, and a historical speakeasy door.
The whole place feels like somebody remembered that history is more interesting when you can still have a drink in the middle of it.
Our Stay Started Better Than Expected
We got to the Fenway much earlier than normal check-in time, and I figured we’d hand over the luggage, wander downtown for a couple of hours, and come back later. Instead, our room was ready.
That will immediately improve my opinion of almost any hotel.
Check-in was friendly, we were given the rundown on the restaurants, bars and live music, and then they offered us a welcome drink made with raspberry liqueur and champagne. We had been in the building for maybe five minutes.
Vacation officially started.
When we got upstairs, my first reaction was, “This is a big old room.” And it was. We had a good view toward the bay, a refrigerator, plenty of room to spread out and, waiting for us, a little Fenway welcome package.
There was a candle inspired by Dunedin’s citrus history, locally made popcorn, Fenway sunglasses, a small bottle of champagne and a welcome card. None of that is going to make or break a hotel stay, but it did something more important. It made the place feel like somebody had thought about us arriving.
Jodie summed it up perfectly:
“That’s cute. That’s a cute little welcome.”
Then we opened the champagne.
“To our vacation.”
More specifically, to the second part of it.
Location: Close Enough to Downtown, but Not in the Middle of It
The Fenway sits on Edgewater Drive overlooking St. Joseph Sound. Downtown Dunedin is close enough that walking is absolutely possible, and the hotel and regional tourism material both sell that walkability as one of the property’s advantages.
We did plenty of walking during the trip, although we’re also not going to pretend we abandoned the car for three days and lived some perfectly curated pedestrian vacation. We drove, especially when we wanted to explore the causeway and Honeymoon Island or when Florida reminded us that August is basically the surface of the sun with palm trees.
But having downtown nearby matters. You aren’t staying at an isolated beach resort where every meal has to happen inside the property. You can walk into town, explore, eat somewhere else, grab a drink, and come back.
Or you can do what we did on the first night and realize that one of the better dinners of the trip is already downstairs.
HEW Was Supposed to Be Dinner. It Became Part of the Story.
HEW Parlor & Chophouse is the Fenway’s signature restaurant. The name isn’t just somebody trying to make “hew” sound steakhouse-ish. It also comes from Herman Everett Wendell, the architect associated with the original Fenway. The hotel itself identifies HEW as Wendell’s namesake restaurant.
That’s a neat little connection, but history isn’t why I’d tell somebody to eat there.
The food is.
We almost talked ourselves out of dinner at HEW because we knew we had several other places we wanted to try around Dunedin. Then we realized the restaurant’s dinner schedule wasn’t going to line up with the rest of our stay.
So downstairs we went.
Good decision.
Let’s Start With the Drinks
Our server was Kaitlyn — or, as she jokingly became in my notes, Kaitlyn 2.0. She knew the menu, knew the steaks and, importantly, didn’t act annoyed while we asked entirely too many questions.
One of our cocktails was Dewey’s Purple Heart, which arrived with its own little potion bottle. That is the kind of completely unnecessary presentation that I love. It’s a drink. It doesn’t need a potion bottle.
Which is precisely why I’m glad it had one.
The Purple Heart cocktail also has a personal story behind it tied to people at the Fenway, although some of the details we heard varied depending on who was telling us the story. So rather than turn somebody else’s family history into an internet game of telephone, I’ll leave it at this: it wasn’t just a random cocktail name.
Then came the dirty martinis. We both like a proper dirty martini, and these were excellent. The blue-cheese olives were stuffed in-house instead of being those aggressively brined pre-stuffed things you sometimes get.
I bit into one and said:
“That might be the best blue-cheese stuffed olive I’ve ever had in my life.”
That’s admittedly a very specific award category.
Still counts.
The martini itself was dirty enough without having to ask for it extra dirty. Again, very specific standards around here.
The Pierogi That Wasn’t Really a Pierogi
We started with what the menu called a deconstructed pierogi. The presentation looked more like gnocchi with pierogi ingredients scattered throughout it.
Was it technically a pierogi? I have no idea.
Do I care? Not even a little.
Whatever they wanted to call it, it was outstanding. Ricotta, cheese, prosciutto and all kinds of rich, salty goodness were happening in there.
We both loved it.
This would become a theme.
Jodie Did Something Unexpected
Jodie almost always orders a filet. It’s her steak. She knows what she likes.
This time, after talking through the cuts with Kaitlyn, she went with the American Wagyu flat iron. That was a gamble.
It paid off.
The flat iron was remarkably tender and had more beef flavor than a typical filet. Later, Chef de Cuisine Sean came out and talked with us about it.
He explained that flat iron is normally a less expensive cut, but when you start with American Wagyu, you’re getting the marbling and tenderness without automatically jumping into the eye-watering price of some of the more famous steak cuts. Their source on that particular night was Linz, although Sean said sourcing can vary.
That conversation was one of the things I liked most about HEW. Nobody gave us a rehearsed speech about “our culinary journey.”
We were two people who enjoyed the meal, asked questions and wound up talking to the chef about meat.
That’s much more our speed.
I Had the Delmonico
I went with the Delmonico. Mine might have landed a little closer to medium than the medium-rare I ordered.
And because somebody will inevitably read that sentence and assume I’m about to demand the chef’s resignation:
Relax.
It was still a very good steak. Plenty of beef flavor. Good crust. I’d order it again.
A steak being a shade past where I ordered it doesn’t automatically transform dinner into a federal emergency.
Now We Need to Talk About the Mac and Cheese
The mashed potatoes were excellent. That deserves mentioning because restaurant mashed potatoes have an annoying tendency to arrive whipped into something with the texture of wallpaper paste.
These didn’t.
They still tasted like potatoes.
But the five-cheese mac and cheese was ridiculous. There was an actual cheese pull.
Sean explained some of the sauce preparation to us — essentially a Mornay-style cheese sauce — but what I actually wrote down was:
“That was ridiculous, man.”
That’s probably the more useful review.
Jodie makes very good mac and cheese herself, which means I’m usually fairly cautious about praising somebody else’s too enthusiastically within earshot.
This one was safe.
Very safe.
It Wasn’t Cheap
Dinner for the two of us wound up around $200 before the final tip, including steaks, appetizer, sides and a few cocktails.
So no, this is not my recommendation for, “Where can we grab a cheap bite in Dunedin?”
But we knew what kind of restaurant we were walking into. And unlike some expensive steakhouse meals we’ve had, I didn’t leave HEW wondering why we just spent that much money.
There is a difference between pricey and overpriced.
For us, HEW landed on the correct side of that line.
HEW Is Also Worth Knowing About for Brunch
We came back the next morning and discovered something I hadn’t really considered: HEW does a legitimate brunch.
Not a sad hotel buffet.
A real menu.
And it’s weird enough to be interesting.
One option immediately jumped out at me: Cheddar Biscuit & Gator Gravy.
Yes.
Gator gravy.
The biscuits were house-made, with the server comparing them somewhat to cheddar biscuits, and the gravy incorporated gator and andouille sausage.
I ordered my eggs over medium. This seems like a small thing, but somebody in that kitchen actually knows what “over medium” means.
No uncooked egg white.
Yolk still yellow.
Perfect.
The gravy and biscuit were rich and extremely filling. I wouldn’t have minded a little more heat, but it was good.
Jodie ordered the Sweet & Spicy Monte Cristo — ham, Swiss, Parmesan-crusted bread, hot honey and powdered sugar.
Her first reaction was basically, “This is definitely different.”
Followed quickly by, “This is really, really good.”
But something was missing.
Jam.
They brought out a house-made berry jam.
That did it.
“That’ll make it perfect.”
And it pretty much did.
HEW currently continues to offer brunch, including a Sunday jazz brunch, although restaurant hours and menus change, so I’d check the current schedule before planning a stay around a specific meal.
Then There Was the Bar Downstairs
One of the unexpected highlights wasn’t really a “thing to do” at all.
We sat at the bar. There was live music. We talked to Amy, the bartender.
And we stayed.
Amy knew cocktails, knew the hotel and knew the local food scene. Jodie ordered an espresso martini, and Amy made it using fresh espresso.
That sounds obvious.
Apparently it isn’t.
She explained that shaking the warm espresso over ice helps create the foam, versus versions made with cold brew or shortcuts. Jodie could taste the difference immediately.
It tasted like somebody had actually put some care into it.
I eventually got talked into a banana-and-rum old-fashioned-style drink. I am suspicious of banana-flavored anything because fake banana has a tendency to taste like somebody melted a yellow popsicle into cough medicine.
This didn’t.
It tasted almost like banana bread.
Dangerously good.
We also got restaurant recommendations, Dunedin stories and more information about the Fenway than we ever would have gotten from reading the little binder in the room.
Again:
Talk to people.
About That Speakeasy...
The Fenway’s history includes a Prohibition-era speakeasy story. There’s still an old door and historical display downstairs that immediately made me want to know what was behind it.
Unfortunately, not a speakeasy we could just walk into.
The hotel’s current Room 27 is a 1920s-inspired speakeasy experience associated with HEW, and the hotel says it operates for themed evenings and intimate events throughout the year. During our stay, it wasn’t available.
Amy also explained that the original historic speakeasy space itself is no longer functioning as the bar people might imagine when they see that old door.
So if you’re booking the Fenway specifically because you’re picturing yourself giving a secret knock and disappearing underground every night, check the current Room 27 schedule first.
I was a little disappointed.
I’m not going to lie.
I like a speakeasy.
But I would much rather tell you we couldn’t get into it than pretend every amenity advertised somewhere on the internet is automatically available every night of the year.
Hi-Fi Rooftop Bar
Eventually, you have to go upstairs.
The Hi-Fi Rooftop Bar sits at the top of the Fenway overlooking St. Joseph Sound, with views toward Honeymoon and Caladesi islands. Marriott currently lists it as serving cocktails, beer, wine and a smaller food menu.
We went up for sunset.
So did everybody else.
This is apparently not a secret.
The rooftop gets increasingly busy as sunset approaches, particularly along the rail facing the water. People take pictures. They move around. They grab their drinks.
Everybody waits.
Then the hotel does something wonderfully old-fashioned.
They count down the sunset.
At the end, somebody gets to hit the cymbals three times.
And somehow Jodie and I got asked if we wanted to do it.
Of course we did.
Except I had my camera in my hand, and she was recording video.
So we both basically said:
“No, you go ahead.”
Travel bloggers.
Asked to participate in the actual experience.
Too busy documenting the experience.
That pretty much sums up modern travel.
Rooftop Food: Good Burger, Questionable Truffle
We ate upstairs another night. I ordered the Black & Blue burger, truffle fries and fish dip. Jodie had the McHEW burger.
The burgers were good. My Black & Blue was exactly the kind of burger I expected: big beef flavor, gorgonzola, bacon, onion, greens and barbecue sauce.
The fish dip had a little smoke to it and was good enough that I’d order it again.
The truffle fries?
No.
Not bad fries.
Just not particularly truffley fries.
I wrote down:
“If you think you’re gonna get a truffle flavor in your truffle fries, you’re not. They just tasted like fries.”
I stand by that.
The rooftop food was perfectly enjoyable, but if you make me choose where to eat at the Fenway, I’m going downstairs to HEW.
And I’m ordering that damn mac and cheese again.
Then the Sky Started Doing This
The first night’s dinner ran long. We were full. Going back to the room sounded pretty good.
Then we looked outside.
The sky over St. Joseph Sound had turned orange, then gold, then pink. The palms became silhouettes, the light hit the water, and every few seconds the whole thing changed again.
We almost missed it.
That’s the part I keep coming back to.
We travel because we want to see beautiful places. Sometimes we spend hours on planes or cross oceans looking for them.
And then Florida does this about ten minutes from your dinner table.
The second night’s sunset was beautiful too, but the first one had storm clouds sitting in just the right places, and it was one of those skies you know isn’t going to repeat itself exactly the same way.
I took entirely too many pictures.
I’m not apologizing.
The Pool Eventually Won
One afternoon, after spending the better part of the day driving around, taking pictures, gathering information and generally turning our vacation into a work assignment, we came back to the Fenway.
Jodie wanted pool time.
And I realized something embarrassingly obvious.
We were staying at a nice hotel with a pool.
Maybe we should actually use it.
The Fenway has an outdoor pool for hotel guests, but what the website cannot tell you is how good it feels to finally stop doing things. It’s not some giant resort pool with waterslides and a DJ. It’s a smaller, comfortable pool area where you can actually relax, cool off, and have a cocktail nearby without feeling like you’re in the middle of an amusement park.
So we stopped.
No research.
No museum placards.
No restaurant scouting.
No “we should probably go see…”
Pool.
That was it.
At some point you have to stop researching the vacation and actually have the vacation.
The People Made a Difference
The Fenway is beautiful, HEW was excellent, and the rooftop view is hard to beat. But when I think about the stay, I also remember the people.
Kaitlyn patiently walked us through steaks. Sean came out to talk about the food. Amy made cocktails and gave us local recommendations. Adrian helped us more than once, and I eventually made him confirm his name because I’d already decided he was going into the blog.
That’s the part hotels sometimes underestimate.
You can spend millions renovating a historic building. You can put a rooftop bar on top. You can build a beautiful restaurant.
And one uninterested employee can still make the entire place feel cold.
The opposite happened here.
The Fenway felt lived in.
So, Would We Stay at the Fenway Again?
Yes.
Very easily.
But I don’t think it’s the right hotel for everybody.
If your priority is walking directly out of your room onto a Gulf beach, this isn’t that. If you want a giant resort with waterslides and 14 restaurants, this isn’t that either.
The Fenway makes more sense for somebody who wants Dunedin.
You want to be near downtown. You appreciate an old building. You like a good restaurant, cocktails and live music. You want a pool where you can relax with a drink. And when the day is over, you would rather walk upstairs and watch the sun disappear behind St. Joseph Sound than fight traffic back to some anonymous highway hotel.
That’s where the Fenway got us.
It wasn’t simply somewhere we stayed while visiting Dunedin.
It became one of the reasons we enjoyed Dunedin.
And then there was that sunset.
Yeah.
I’d stay again.
More from our Dunedin trip
The Fenway was our home base. For everything beyond the hotel, read our three days exploring Dunedin, then come along for Honeymoon Island, Caladesi planning tips and the story behind those painted oranges.
What a gem! Gorgeous views. Sunsets are spectacular. Love the vintage feel.