A girls’ getaway demands not only quality time together but a destination that offers it all – an attractive place with great food and drink and plenty to do for a variety of interests. Writer Chelle Koster Walton and her long-time friends found just that in Dunedin, Florida. Real Food Travelers don’t have to be on a girls’ trip to take advantage of all the area has to offer though. Use Chelle’s article to get planning. 

Save this article to Pinterest to help you plan your own girls getaway to Dunedin, Florida. Photo by Chelle Koster Walton. Graphic by RealFoodTraveler.com.

The Many Ways a Dunedin Girls’ Getaway Takes You to Scotland, Greece, and Florida’s Finest

The final full day of our girls getaway ended with a crash, a toast, and a show like only Mother Nature can manage.

The bartender had instructed me to crash the cymbals three times as he counted down to sunset. Nice touch, the cymbals, and perfectly fitting for the Hi-Fi Rooftop Bar at Fenway Hotel in Dunedin, Florida.

Cymbal clangs ring in sunset at Hi-Fi Rooftop Bar. Photo by Jani Stone.

The instrumental nod honors the bar’s past as WGHB broadcasting studio for Pinellas County’s first radio station back in 1925. The entire resort, part of the Marriott Autograph Collection, takes its cues from retro jazz and music vibes. (The WiFi password is “pushplay.”) Earlier, we had listened to a live jazz soloist on stage in the hotel lobby. It was a festive finale for a reunion of four friends supporting each other through some tough times.

Fenway Hotel is a great place to stay for a girls’ getaway in Dunedin, Fl. Photo courtesy of Fenway Hotel.

A Wee Bit of Scotland in Dunedin

We met in Dunedin from different parts of Florida. It had been 20 years since I’d spent time with two of the old friends. We all hadn’t gathered since our kids were in grade school together and we led the PTA. The four of us had decided upon Dunedin as we looked for a small, walkable downtown suited to shopping, dining, and the occasional adult beverage.

We didn’t know yet about Dunedin’s reputation as a destination for lunching and day-drinking, which draws weekenders from the Tampa-St. Pete metro area. But we quickly discovered it as we arrived to meet at Casa Tina for lunch. And margaritas, of course. Really good margaritas.

In addition to great margs, Casa Tina serves authentic cuisine such as Enchiladas in Salsa Rojas.

The place was packed, and the charmingly compact downtown area thronged with shoppers licking ice cream cones from Strachan’s and scanning a delightful mix of gift shops, toiletry boutiques, art galleries, and one-of-a-kind stores, including my favorite, the Celtic Gift Store. It pays homage to Dunedin’s rich heritage. Of that reputation, I was well aware from numerous trips for work and with my late husband.

The Celtic Gift Store is a must-stop during a girls getaway in Dunedin.

Two Scottish gents named the city of Dunedin for the Gaelic translation for Edinburgh, as the tale goes. Today, this sister city of Stirling, Scotland, boasts a robust population of Scottish and Irish residents who take pride in their heritage.

Hang around the sweet, little downtown hub on a weekend, and you’re likely to hear bagpipes and drums. Student groups and adult bands often gather around John R. Lawrence Pioneer Park, decked out in tartan kilts, to make music and dance traditional highland steps.

Every April, Dunedin Highland Games super-celebrates its heritage, and in November, there’s the Dunedin Celtic Festival.

Explore more of the town’s background at the Dunedin History Museum tucked into a red-brick, circa-1924 train depot between shops and restaurants on Main Street.

Set on the bayfront facing Clearwater Beach and offshore barrier islands, Dunedin also huddles around the Pinellas Trail, a 60-mile rail-to-trail, paved pathway that starts to the south downtown St. Pete.

Dunedin is also gateway to two of Florida’s most gorgeous barrier islands, home to state parks and lovely stretches of white beach. You can drive to Honeymoon Island State Park – be sure to stop at its nature center. From Honeymoon, a ferry shuttles back and forth to Caladesi Island State Park, an absolute gem for taking your girls getaway way away.

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Girls’ Getaway in Tarpon Springs: Fast Track to Greece

From Dunedin’s upbeat Gaelic character, it takes less than a half-hour to reach the virtual shores of Greece in Tarpon Springs to the north. It’s a must-do side trip when you’re in Dunedin. Our visit started off on a somber note with a stop at the little-known, off-the-mainstream, uniquely Tarpon Springs Saint Michael Shrine.

We were honoring the birthday of one friend’s recently deceased son and the anniversary of the death of another in the group’s daughter at a shrine devoted to the miracle of a son saved from death by Archangel Michael. The visit to the tiny rock chapel fitted with an altar, Greek religious icons, and a handful of pews was an emotional but cathartic experience for us all – candles lit, hugs shared, tears shed.

Most come to Tarpon Springs for the grand, onion-domed St. Nicholas Greek Orthodox Cathedral and the sponge docks along Dodecanese Boulevard.

Greek restaurants and bakeries, touristy shops selling sponges and tchotchkes, boating charters, and the Spongeorama (somewhat decrepit, very touristy, but fun in an offbeat way) attraction line the waterfront street.

After a Dodecanese drive-by, we opted instead for a visit to Sunset Park Beach, which was empty midday. (A different story at sunset, however.) We then took our shopping cravings to historic Tarpon Avenue, where merchandise is novel, girls-geared, and affordable. Our favorite shops: the Healing Hedge Witch and One Amazing Find.

In addition to the Strachan’s Homemade Ice Cream on Dunedin’s Main Street, another lies on the outskirts along Alternate Highway 19 en route to Tarpon Springs. On the return trip, we stopped for its renowned carrot cake and scoops of coffee ice cream to boost our energy for our last night of celebration together.

Strachan’s Homemade Ice Cream is renowned throughout the Tampa Bay area.

Food & Drink in Dunedin, FL

Before we even headed to Dunedin, our texts and emails were obsessed with where we would eat on our girls venture. Truthfully, besides our frequent trips down memory lane, food was the hot topic of conversation throughout our three days together. So, eating and drinking were clearly priorities.

Did we make it to the Fenway pool? Did we visit museums? Did we bike the Pinellas Trail? No, no, and no. If it didn’t involve food, drink, or shopping, it got deleted from the itinerary. There were, as the saying goes, just too many good restaurants, too little time.

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Starting off with that first lunch a Casa Tina, we set the bar high. A local institution since 1992 (when our kids were 2-years-old), it does authentic Mexican cuisine in an unfancy, but highly decorous setting of crucifixes and wood carvings.

Fenway Hotel proved a worthy source of delightful nourishment right on property. As the sun tipped horizon-ward, we noshed at the a-buzz Hi-Fi Rooftop Bar on hickory-smoked fish dip, tennis ball-sized meatballs, and warm lemon cream spinach and artichoke dip.

Friends enjoying the sunset on the Hi-Fi Rooftop Bar while on a girls’ getaway.

We did brunch at the hotel’s flagship restaurant, HEW Parlor Bar & Chophouse. Don’t pass up on the chevre grits, an unspeakably clever twist on classic cheese and grits. The out-of-the-ordinary menu has a distinct Southern lean: beignets, orange custard-soaked brioche French toast, cheddar biscuit and gator sausage gravy, brisket and hash.

For our last night, we crossed off a bucket-list restaurant for me. Bon Appetit has been around as long as I can remember, known not only for its continental excellence but its sweeping views of St. Joseph Sound. Cocktails like the White Linen – Nolet’s Silver Gin, St. Germaine liqueur, fresh lemon, and muddled cucumbers – started things off on just the right note of celebratory.

The White Linen gin cocktail at Bon Appetit.

The food menu covers all continental bases from gnocchi Bolognese to bouillabaisse and fine steaks. In this part of Florida, close to Tarpon Springs, Greek influence seeps into local cuisine far beyond city limits. Having missed the timing for a meal in Tarpon Springs, I chose Bon Appetit’s signature grouper dish sauteed with heirloom tomatoes, capers, feta cheese, and lemon butter sauce; served with refreshing cucumber salad. A delightful collision of Florida and Greece.

A Grouper dish at Bon Appetit takes cues from Greek kitchens.

If you are looking for true Greek in Tarpon Springs, I have suggestions from many years of feasting there a la My Big Fat Greek Wedding. My favorite, right in the thick of things on Dodecanese, Dimitri’s on the Water offers porch seating overlooking the Anclote River and goings-on of the spongers. A hard-core devotee of Greek cuisine, I inevitably go for the avgolemono soup and dolmades. Or rack of lamb, when I’m splurging.

Then I hit Hellas Restaurant & Bakery, across the street and painted with Greek travel murals inside, for a pastry to go. Opa! the baklava cheesecake! To escape off the eaten path, I hit Costas Restaurant for fried smelts and a cozy, family atmosphere.

Back in Dunedin, I recommend the highly lauded landmark The Black Pearl for fine dining; Dunedin Brewery for uber-casual, from-scratch pub food (boasting Dunedin’s first poutine, the menu proclaims) with live music and microbrews.

Get your morning java jolt and a pastry at Dunedin Coffee & Bakery. That’s where we gathered for goodbye hugs to seal three days of giggles, gossip, tears, memories, music, and the food that tied it all together.

To learn more about visiting Dunedin, Florida, visit their tourism website at VisitDunedinFL.com.

-Story and photos, except where noted, by Chelle Koster Walton