Note: This guide first appeared in our email newsletter series, One Day in Tampa Bay. Subscribe to that newsletter and check out our other offerings at tampabay.com/newsletters.
One of northern Pinellas County’s most beloved small towns (and a sister city to Stirling, Scotland), Dunedin never ceases to charm with its ample restaurants, craft breweries, year-round festivals and miles of paved biking trails.
Though Dunedin — it’s pronounced done-EE-din — extends far beyond the quaint Main Street Historic District, for the purposes of this newsletter we’ll be focusing on the bikeable and walkable downtown area, which sits right along the Fred Marquis Pinellas Trail.
The full Pinellas Trail extends from St. Petersburg to Tarpon Springs. We’ll tell you how to use Dunedin as your launch point to pedal along the trail, but there’s also plenty to do if you feel like staying put and roaming downtown.
Hit the Pinellas Trail
Right off the trail on the corner of Skinner Boulevard and Douglas Avenue, Kafe Racer is the perfect spot to pick up a pair of wheels before you hit the trail. The shop’s user-friendly reservation system includes several laptops that link directly to its website, where you can pick and choose from several different models. Among them: hybrids, road bikes, electric bikes and beach cruisers.
There’s also a cute cafe with pastries if you want to fuel up before the ride (or grab gelato after!).
Times tip: We got lucky, snagging late-afternoon bikes on a sleepy Wednesday, but the shop can book out quickly, especially during the busy spring season and on holidays, so it’s best to make reservations ahead of time online. Customers book bikes for the day, so start early to get the most bang for your buck.
Heading north on the trail, you’ll pass plenty of parks where you can hop off and explore. First up is Josiah Cephas Weaver Park, overlooking St. Joseph Sound. A little farther north, you’ll pass by Hammock Park, a nature preserve with boardwalk trails and a butterfly garden, and Stirling Park.
Along the way, admire the view: scenic greenery and lush tropical plants, lots of cute backyards with quirky decorations and impressive landscaping.
Next up, on your left, you’ll pass the turnoff to the Dunedin Causeway leading to Honeymoon Island State Park, where you can hike through miles of mangrove-lined trails or hop on a ferry to beautiful Caladesi Island State Park.
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Farther north, you’ll pass through the tiny town of Ozona and then Palm Harbor before eventually passing by Wall Springs Park, a 210-acre park featuring historic freshwater springs.
At some point, you might be ready for a refreshment or a break. We recommend pulling off in Palm Harbor at de Bine Brewing Company, a great brewery and taproom with frequent live music just steps away from the trail.
Dunedin has a ton of downtown parking, but the best spot is the covered garage at 365 Monroe St., just steps away from the Pinellas Trail.
There’s a public restroom along the Dunedin Causeway on the way to Honeymoon Island State Park and several more restrooms in the park.
Enjoy downtown Dunedin
You’ll find plenty to see throughout Dunedin’s historic downtown, and there is great shopping along Main Street.
Back in the Day Books is the spot for both buzzy new titles and obscure old finds. (Owner Boe Rushing has done stints as president of the Florida Antiquarian Booksellers Association.) There’s an impressive selection of Florida-themed books by local authors, and the folks behind the counter are more than happy to share recommendations.
Have out-of-town guests looking for upscale souvenirs? Or just want some cute Florida kitsch for your own home? Key West Express Boutique is the spot for all things Sunshine State. We recommend the shop’s candles that smell just like a day at the beach. As a bonus, many items for sale are made by locals.
The Celtic Shop of Dunedin is a great place to explore the city’s roots, peddling Scottish-, Irish- and Welsh-imported goods. Bestsellers range from scones and haggis to Celtic jewelry and custom kilts.
Times tip: In the late 1800s, the city was originally called Jonesboro. A guy named George Jones put the name on a sign above his general store. Two Scottish men came along, decided they had a better idea and opened a post office that they dubbed Dunedin (the Scottish Gaelic translation of Edinburgh, their hometown). The name stuck, and so did the Scottish flair. Every year, locals gather for the Dunedin Highland Games, which includes a gathering of clans, sheepdog demonstrations and bagpipe competitions. The city of Dunedin, plus the local middle school and high school, all have their own pipe bands as well.
There’s no shortage of fantastic restaurants in Dunedin, and the selection spans from fast-casual to seafood to fine dining.
At Caracara, you’ll find creative twists on fusion fare, including the must-have crab nachos and gingery carrot salad. Next door at Dunedin Coffee Company & Bakery, cozy up with a cappuccino and a pastry. And over at nearby Jack Pallino’s you’ll find yummy brick oven-cooked pizzas and a sports bar vibe.
The ambience can’t be beat at Casa Tina, a wildly popular Mexican restaurant that’s been a downtown Dunedin staple for the past 30 years.
For a special occasion or romantic evening, The Black Pearl is the place to go.
Looking to chow down on the best fish sandwiches and seafood dishes? Olde Bay Cafe, Hog Island Fish Camp and Lucky Lobster Co. are all solid bets.
Those with a sweet tooth should look no further than Strachan’s Ice Cream, a beloved local institution and the purveyor of our absolute favorite ice cream flavor ever, Carrot Cake Cake Batter. Really, it’s amazing.
Grab a drink
Dunedin is known for its impressive number of breweries, including Dunedin Brewery, the state’s oldest microbrewery. Some of our favorites include Cueni Brewing Co., Dunedin House of Beer, Woodwright Brewing Co. and 7venth Sun Brewery, all of which are conveniently located either directly off of or within walking distance of the Pinellas Trail.
For something nonalcoholic and refreshing, check out Lane’s Lemonade, which sells freshly squeezed lemonade, limeade and orangeade.
If spirits are more your thing, grab a seat at Sonder Social Club, where bartenders shake up some of the best craft cocktails in the area.
Our favorite spot for a drink? The rooftop of the Fenway Hotel. From here, you’ll get the most scenic views of St. Joseph Sound. And we dare you to find a better place to catch the sunset.
Check out our other local guides
- Downtown Tampa guide: How to explore Riverwalk and beyond without a car
- Pinellas County beach guide: Where to eat, drink and relax along the Gulf
- Safety Harbor guide: Plan a day of indulgence, from pizza to public art
- Tarpon Springs guide: Explore Greek food, the Sponge Docks and beyond