The Best Things To Do In Dunedin, Florida

Outside Woodwright Brewing Company in Dunedin, strings stir the tempo of the otherwise unhurried coastal air. Fiddles mingle with mandolins, banjos, and guitars in a traditional bluegrass style that’s well orchestrated without feeling a bit rehearsed. One musician takes center stage, singing his part before giving the next person a go. Every solo adds to the splendor without stealing the show.

The same is true for the rest of Dunedin (pronounced “done-EE-din”). This slender Florida spot, located about 24 miles from Tampa, finds harmony in community. Its state-protected shorelines and hand-painted storefronts make first-name greetings far more common here than big crowds. Neighbors collaborate on town ventures while everyone—from artists to pitmasters—sprinkles a sense of history into Dunedin’s next chapter. The result is an unexpected Gulf Coast haven that feels familiar yet wholly uncharted.

Meander downtown, and you’ll wonder how this laid-back locale has remained under the radar. Independent shops, watering holes, and restaurants painted in vibrant, happy shades line Main Street in a way that will make you nostalgic for vacations past. A longtime destination for snowbirds, especially fans of the Toronto Blue Jays, who come here for spring training, Dunedin has been quietly evolving. Progress that feels organic but entirely intentional has built an escape that blends beach-town simplicity, a growing brewery scene, and proximity to untamed nature.

Town Traditions

While you don’t have to know much about Dunedin’s past to appreciate its present, the history is stamped all around. Scottish flags and annual celebrations commemorate the Celtic heritage here. Sun-weathered paintings of oranges flank the doorways of local businesses—a bright nod to the area’s beginnings growing and packing citrus. “You’re not really a resident until there’s an orange decorating your place,” explains Grant Painter of Woodwright Brewing Company.

Step inside the taproom, and an original Optimist pram boat hanging from the ceiling speaks to the coastal side of Dunedin’s story. In the 1940s, boatbuilder Clark Mills designed them in this very place. Inspired by Soap Box Derby races, they were engineered simply so families could assemble them at home for kids to learn to sail. Now they’re some of the most widely produced boats in the world. “Bringing new life into this old building is about preserving our history and keeping our charm,” says Painter.

Across the street, Chantala and Eric Davis fill the neighborhood with the smoky-sweet smells of their traditions. Lines at Eli’s Bar B Que are commonplace, but so is an overwhelming sense of fellowship. Eric, son of founder Eli, greets nearly every guest by name at the window-service joint that’s open only on Fridays and Saturdays. This style of cooking has passed through generations of his family, with brothers and cousins helping run the pit today. His father’s story is also rooted in the restaurant’s soil; cotton plants stand tall out front. “Cotton is in our families,” Eric says. “When my dad bought this building, he added those as a reminder of his ability to stand on his own right here in Dunedin.”

Island Escapes

Beach bums and nature lovers can get their fill of unspoiled shores just northwest of town. A quick drive over the Dunedin Causeway, Honeymoon Island feels worlds away. Named for its original circa-1940 bungalows that were popular with newlyweds, the island and state park are still secrets for many. The private-seeming public beaches intertwine with walking trails where you may leave the sole footprints.

At neighboring Caladesi Island State Park, which is accessible only by boat, the isolation is intoxicating. Relax on the sand, kayak beside mangrove forests, or stroll the shell-speckled shore. No matter how you unwind, you can plan to be undisturbed. The park is home to hundreds of migratory bird species, protected grass flats, and dolphins. A ferry runs between Caladesi and Honeymoon Islands, but don’t be surprised if you see more wildlife than people.

A Perfect Day In Dunedin

This isn’t the typical Florida tourist spot, and that starts with a stay at the Fenway Hotel. A reimagined icon of the Jazz Age, this convenient base camp just off the main drag features unobstructed views of the St. Joseph Sound. The property’s subtle musical motif reminds guests of its beginnings as a radio station, while the sunset libations at its Hi-Fi Rooftop Bar draw a regular crowd.

Start your day on the oak-lined patio at The Wild Iris Café, and enjoy sky-high quiches and specialty Benedicts among locals. Breeze over to Main Street to shop for treasures at Back in the Day Books and Lafayette & Rushford Home, which supply anything but stereotypical souvenirs. Pedal along the Pinellas Trail, a 54-mile biking-and-walking path that stretches from Tarpon Springs to St. Petersburg, for easy access to stores, eats, and drinks near and far.

Off the trail, all roads lead to a pint at one of nine beer makers within a single square mile. At Dunedin Brewery, Florida’s oldest microbrewery, posters and Scottish paraphernalia pepper every inch of the interior. The town’s ancestry comes alive as you sip, with photos of pipe bands and Highland dance groups honoring champions from recent decades. Their craft selection and passion paved the way for others to scale up their own home-brewing hobbies, spurring a local beer boom. Enjoy a pour of hefeweizen at Woodwright Brewing Company, an IPA at Caledonia Brewing, or an English ale at Cueni Brewing Co.

Pull up a barstool for lunch at Olde Bay Café, a no-frills seafood dive overlooking the marina. Or settle in for shareable plates with international flair (like osso buco or tempura squash blossoms) outside The Living Room, where diners often bring their dogs. Reserve a window seat before sunset at Bon Appétit Restaurant to experience the Gulf’s glory on full display, or head downtown to delight in Casa Tina’s bright spread of tacos, enchiladas, and ceviches. Save room for a scoop from Strachan’s Ice Cream & Desserts. Then grab a nightcap at Sonder Social Club, or end your evening with tropical beats and rum-based drinks at The Honu Restaurant.

Although sunny getaways dot St. Joseph Sound, don’t overlook Dunedin. Between wild shores and captivating town character, you’ll find plenty of reasons to anchor down in this Florida retreat. As Eric Davis puts it, “Why not Dunedin?”

Getting There

Located about 5 miles north of Clearwater, Dunedin is convenient to Tampa International Airport (TPA), around 20 miles away, and St. Pete-Clearwater International Airport (PIE), about 12 miles away. Downtown Dunedin is very walkable, but you’ll need a car to access areas beyond the town center, like Honeymoon Island.