The Best Experiences in Dunedin, FloridaDiscover the best experiences in Dunedin, Florida! From waterfront trails and charming downtown vibes to beaches, markets, and outdoor adventures, this guide highlights the top things to do in one of Florida’s most lovable coastal towns. 🌴☀️🌊AuthorsAFST
DestinationsDunedinItinerary

Main Street

Main Street
Main Street in Dunedin is where small-town charm meets coastal cool. This street is often brimming with energy as locals and visitors alike stroll from one unique spot to the next—craft breweries, vibrant restaurants, quirky boutiques, and art galleries that capture the town's uniquely creative spirit.
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A Place to Stay

Fenway Hotel, Autograph Collection
Stay at The Fenway Hotel, known for its rich history and unique charm, featuring luxurious Mediterranean-inspired design. Built in 1924, the hotel hums with soul and has long been a gathering place where guests and locals come together to dance the night away. It also served as the county’s first radio station.
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Book

Must Try Eats

The Black Pearl
The Black Pearl is your go-to for one of the best fine dining experiences in the region.
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Dunedin Brewery
Dunedin Brewery, Florida’s oldest microbrewery, offers fresh ideas on tap and live music.
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Caledonia Brewing
Caledonia Brewing is Florida’s oldest microbrewery.
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Casa Tina Mexican
Casa Tina offers delectable Mexican cuisine and lively art.
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Outdoor Adventures

Caladesi Island State Park
Caladesi is reachable only by boat, and that's what makes it a true haven for nature lovers. There are no condos or hotels here, just soft white-sand beaches and clear blue waters. The mangrove forests teem with life, and one can often see dolphins playing in the waters nearby. Hike the Beach Loop and Hammock Loop trails to see the island’s unique habitats and try to spot rare bird species.
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Honeymoon Island State Park
At Honeymoon Island State Park, relax on the island’s soft white sands, or head out on the water with a rental kayak or paddleboard to explore the shoreline at your own pace. Hikers can follow the scenic 2.5-mile Osprey Trail, which winds through rare stands of untouched slash pine. Bird enthusiasts will find plenty to watch for—the park is home to a remarkable variety of species, including occasional sightings of rare birds like the bar-tailed godwit, green-tailed towhee, long-billed murrelet, and mourning warbler.
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Fred Marquis Pinellas Trail
Explore the Pinellas Trail, a popular route for biking, walking, and jogging that runs through the heart of Dunedin.
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Highlander Park
First held in 1966, this beloved tradition has grown into Florida’s largest and longest-running Highland Games, celebrating the spirit, music, and athleticism of Scotland. Each year, visitors can enjoy an authentic taste of Scottish culture through world-class competitions in piping, drumming, and Highland dancing, along with thrilling “tests of strength” such as caber tossing, hammer throwing, weight throwing, and shot putting. Winners from Dunedin’s games often advance to national and international championships, including those held in Scotland itself. Beyond the competitions, the festival brings the community together with a stirring military tattoo featuring local school pipe bands, Scottish storytelling, and sheepdog demonstrations.
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Shop, Shop, Shop

Dunedin Downtown Market
Visit the Dunedin Downtown Market in Pioneer Park for local art, produce, and handmade goods.
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