Driveable Destinations: Dunedin

With two state parks, links to Scottish history and a spot on a best small town in the South list, this Florida gem sparkles with possibilities.

Though it’s often referred to as “the home of Honeymoon Island,” Dunedin is much more than the gateway to Florida’s most-visited state park. With a lively downtown, vibrant arts scene and plenty of parks, this charming waterfront community was named No. 39 of Southern Living’s Best Small Towns in the South 2023.

About a million people live in Florida’s most densely populated county, Pinellas, but only 37,000 of them live in Dunedin, a two-hour drive from Ocala—perfect for a day trip or overnight getaway.

Famous Firsts

Dunedin History Museum

Much smaller than its better-known neighbors Clearwater and St. Petersburg, Dunedin was the home of the county’s first radio station, which went on the air in December 1925 from its studio atop the brand-new, three-story Fenway Hotel. 

In 1937, Dunedin resident B.C. Skinner pioneered a new product featuring Florida citrus: Orange juice concentrate. Canned at the Dunedin Concentrate Plant, it was shipped overseas during World War II to provide much-needed vitamins and a taste of home for Allied soldiers. 

A product developed by another Dunedin resident played an even more important role in the Second World War. Originally designed for civil rescue work in swampy regions, Donald Roebling’s amphibious Alligator tank was used as a landing craft by U.S. Marines at Iwo Jima and Guadalcanal.

For more local history, stop by the Dunedin History Museum, located in the town’s former railroad depot, to view historical exhibits and sign up for the popular downtown walking tour.

Island Hopping

There’s a reason more than a million people a year cross the Dunedin Causeway just north of downtown to visit Honeymoon Island State Park: With four miles of pristine white-sand beach along the crystal clear Gulf of Mexico, it’s a paradise for shelling, swimming and birdwatching and features a dog-friendly beach.

Historic Andrews Memorial Chapel

The island got its name in the 1930s when the owner built 50 honeymoon cabins. It has been a state park since 1981.

Before the devastating Tampa Bay hurricane of 1921, Honeymoon and Caladesi Islands were joined and known as Hog Island. The two are now separated by Hurricane Pass and Caladesi is accessible only by boat. Take the ferry from Honeymoon Island to explore the unspoiled Caladesi Island State Park, which boasts white sandy beaches on the Gulf side and a kayak trail through the mangrove forest on the bay side. 

Hallmark Holiday

If you enjoyed the Hallmark Channel’s A Taste of Love, which debuted in February, you can retrace the steps of actors Erin Cahill and Jesse Kove, who filmed the entire movie on location in and around Dunedin. The restaurant owned by the main character’s family is real-life Sea Sea Riders, a local favorite for seafood for three decades. Located in a 1903 Key West-inspired Cracker cottage, it offers indoor dining plus seating on the expansive porch. The movie characters also visit the cozy scratch-kitchen Wild Iris Café, a delicious option for breakfast and lunch, and the “Grand Lady of Dunedin,” the historic Fenway Hotel. You also might recognize Edgewater Park, with its canopy of trees bordering the marina. 

Festival Fun

Downtown Dunedin

Usually laid back, this town loves to party! Home of Florida’s largest St. Patrick’s Day festival, Main Street shuts down for the annual street party going strong after more than 30 years. Presented by Flanagan’s Irish Pub, the celebration includes live music, brews and food with vendors set up in Pioneer Park.

Early Scottish settlers named the town after the Gaelic name for Edinburgh, the capital of their native country, and Dunedin proudly celebrates its heritage. On April 6th, the Dunedin Scottish Arts Foundation will host the 56th annual Dunedin Highland Games and Festival, which features bagpiping, drumming and dancing competitions as well as traditional test-of-strength games such as hammer throwing and shot putting. Attendees also enjoy Scottish storytelling and sheepdog demonstrations.

The highlight of this year’s sixth annual Dunedin International Film Festival, held in February, was a special screening of A Taste of Love two weeks before it debuted on the Hallmark Channel, plus a panel discussion with father-and-son actors Martin and Jesse Kove. The four-day event included dozens of screenings, from local shorts to documentaries to feature films from around the globe.

Fenway Hotel, photo courtesy of Fenway Hotel

Public Art

All Aboard statue

As you explore downtown, be on the lookout for a diverse array of art installations—from the more than 1,000 local pets featured in the Dogedin mural just off Main Street to the postcard-perfect selfie spot by the marina to the colorful 6-foot painted dolphin statues, part of the Clearwater Dolphin Trail. Two of the most unique 3D pieces are located at the old train depot: The bas relief Railroading in Dunedin and the three life-sized bronze statues out front, named All Aboard, featuring a Jazz Age-era woman and her young daughter, clutching her teddy bear, hurrying toward the waiting train conductor.

Chews, Brews and Views

Sunsets over St. Joseph Sound are spectacular and are perhaps best enjoyed relaxing with fine food and drink. Reserve a table at Bon Appetit Restaurant to dine al fresco and savor French favorites and seafood specialties while taking in the panoramic view from the pier. Or stop by the Hi-Fi Rooftop Bar at the Fenway Hotel for the daily sunset celebration to sip crafted cocktails, such as the Fenway Sunset, against a palm tree-framed backdrop of vivid colors on the horizon.

Create a custom pub crawl with eight craft breweries located within a one-mile radius. Start at Dunedin Brewery, founded in 1996 and the oldest distributing microbrewery in Florida, and make your way to the expansive HOB Brewery, facing the Pinellas Trail, where you’ll find 50 taps and two pet-friendly patios.

Pinellas Trail

Hit the Trail

The 75-mile Pinellas Trail is a protected greenspace for walking, jogging, skating and biking located along a former railroad corridor. The trail bisects Main Street in the heart of the downtown dining and shopping district. Get some fresh air as you stroll through neighborhood and wooded sections or rent a bicycle from one of the many outfitters. If you stay at the Fenway Hotel, just a few blocks from the trail, guests receive complimentary rental of on-site bikes. 

Just over a mile north of downtown, the trail connects to Hammock Park with its butterfly garden, majestic oaks and disc golf course. For a longer bike ride, head north for another eight miles to the quaint community of Tarpon Springs, known for its Greek eateries and sponge docks.

When you return to downtown, treat yourself to a scoop of Strachan’s Homemade Ice Cream, located just a block from the trail, or a fresh-squeezed or frozen lemonade from Lane’s Lemonade in the trailside red caboose.

Bon Appetit restaurant

Relax and Stay Awhile

Just a half-mile from the downtown pier, the historic 1920s Fenway Hotel perches above an expansive front lawn facing St. Joseph Sound. Decorative musical touches celebrate its Jazz Age roots and visitors enjoy live music on the lobby stage each evening and at jazzy Sunday brunches in the HEW Parlor & Chophouse restaurant. Relax on the shady front veranda overlooking the water or take a dip in the courtyard pool. 

Be sure to check out the alcove just off the lobby that preserves the entrance to the secret basement Prohibition speak-easy—complete with historic black-and-white photographs—and the rotating collection of artifacts and photos on loan from the Dunedin History Museum. OS

To learn more, go to

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