The Sunshine State is made up of different regions, counties and cities with their own personalities. Visitors who drill down further will find that each city has distinct districts worthy of a stop during your travels. And they are walkable.

By Janet K. Keeler

Florida is not a one-size-fits-all vacation wonderland. The Sunshine State is made up of different regions, counties and cities with their own personalities. Visitors who drill down further will find that each city has distinct districts worthy of a stop during your travels. And they are walkable.

We call them “Cool Blocks.” A survey of the interesting neighborhoods throughout the state led us to ground zero for high-end second-hand retail therapy in Palm Beach County and then to a funky stretch of tropical fun in a place called Matlacha on Pine Island Sound.

We found streets crowded with antiques in inland Arcadia and a cookie-cutter strip mall in Orlando that’s redefining the image thanks to a yoga studio, trendy bakery and a “craft beer parlour.”

Florida may be known mostly for beaches and theme parks, but there’s plenty of unique personality all over the state. Join us on a hip trip.

Cool Blocks in Florida

St. Petersburg

The coolest block in the newly hot and happening downtown is the 600 block of Central Avenue. While high-rise condo and apartment buildings are taking over the landscape of the historic downtown, the 600 block remains decidedly low-rise and funky. Restaurants, water holes, coffee shops and oodles of cool boutiques have taken up residence on the both sides of the main thoroughfare.


Food halls are sprouting up all over the country and Tampa may be home to one of the sexiest. The Heights Public Market at Armature Works on the Hillsborough River is the place to be seen and get a cocktail that’s dripping in attitude. Some 15 food and drink purveyors are drawing crowds to the city’s old maintenance and trolley barn. It was built in 1910 but had been vacant for decades. Now, you may have to fight for a place at the bar.


Small-town charm is what Dunedin is all about. Heck, the main street is even called Main Street. Restaurants and shops, plus a bike trial that bisects the town, are all part of the draw to the walkable downtown. Craft beer has been part of the landscape here for years with several breweries opening recently. It’s a dog-friendly city, too. Visitors often feel like they’ve uncovered a hidden gem. The locals already know that.

Greek history runs deep here and day-trippers come from all over to partake in the culinary delights of the Mediterranean at cafes along the Anclote River. From spanakopita to pastitsio and a multitude of Greek pastries, the restaurants on Dodecanese Avenue mimic the outdoor eateries of the islands. Sponges harvested just off the coast are sold in many souvenir shops. You know you’re in Florida when you walk the coolest street of Tarpon Springs but it just doesn’t feel like it.

The population of this Panhandle city swells to triple its size come summer when vacationers from nearby Southern states arrive. For many, this is their home away from home. The beautiful beach is the main attraction, but so are fishing, shopping and a variety of outdoor activities. When the sun goes down, miniature golf and small-scale amusement parks keep the party going. There are lots of cool blocks here because every square inch of Destin screams vacation fun.

Orlando, Audubon Park

When you find a nondescript strip mall with an anchor business called Redlight Redlight Craft Beer Parlour, you know you’ve stumbled on a happening place. Redlight Redlight specializes in sours and that’s beer that will make you pucker up. The 2800-2900 block of Corrine Drive in the Audubon Park Garden District boasts a bakery that specializes in pies, a record store that deals in vinyl and sells tickets to local music venues, and a few vintage clothing shops, among other businesses.

Orlando, Thornton Park

In the shadow of the downtown skyscrapers is Thornton Park. It wraps around picturesque Lake Eola, where you can flex your calf muscles in small paddleboats shaped like swans. This is a trendy, gentrified neighborhood that more and more people are calling home. It’s a popular spot on Sundays for brunch and the Sunday outdoor farmers market. Order horseradish-spiked deviled eggs, boiled peanut hummus and chicken-fried cauliflower “steak” at Southern Contemporary Cuisine, just one place putting a twist on culinary classics.

Winter Garden

The coolest block in Winter Garden is air-conditioned. The Plant Street Market is a new building made to look old with its brick construction. Under one roof are vendors selling everything from locally sourced pork belly to organic beets to candles crafted from soy wax. The anchor is Crooked Can Brewing Company where beers range from German-inspired kolsch and Oktoberfest to Irish red, Belgian strong ale and a Florida-kissed brew dripping with citrus. Don’t be surprised if you see lots of bikers toting helmets under their arms. The tracks that once carried the train through the middle of town are now part of the 22-mile West Orange Bike Trail.


The Five Points neighborhood of Jacksonville sits across the St. Johns River from downtown but couldn’t seem farther away with its Bohemian attitude. Park Street is where you’ll want to wander, leaving time to catch an art house flick at Sun-Ray Cinema. A vintage mall has oodles of stalls to wander through, bring your laptop or knitting to a casual and comforting brew and tea salon and then pick from a number of restaurants for breakfast, lunch or dinner.

The coolest block in this iconic Florida vacation town is miles long and paved by sand. Yeah, you can drive your car or motorcycle on the hard-packed sand and still pitch an umbrella to enjoy a day in the sun with the roar of the Atlantic Ocean at your feet. But the town known for spring break, NASCAR and motorcycles is undergoing another transformation to attract a new audience thanks to new restaurants with amazing views of the water. Yoga with an Atlantic view, anyone?

Jensen Beach

Once known as the “Pineapple Capital of the World,” Jensen Beach has kept its friendly ways but transformed into a haven for artists and lovers of all things on the water. Its compact downtown boasts shops and restaurants and there are plenty of places to rent watercraft or arrange for a fishing excursion. For those who want to remain landside, a tangle of colorful cottages is now artists’ studios that are open to visitors.


SW Osceola Street is the place for an afternoon ramble in Stuart, the “Sailfish Capital of the World.” This small town with just 16,000 residents is steeped in Florida history and there are murals around town that spell that out. But a visitor might find the number of posh home furnishing and clothing stores here surprising. Think pink flamingos on pricey silk pillows. The local cuisine is all about seafood, with a few mighty fine places to partake in oysters on the half shell.

The streets in Arcadia are lined with antiques. Literally. Besides the 20-plus antique and vintage shops on Oak Street, the fourth-Saturday Arcadia Antiques Fair brings visitors looking for everything from old Coca-Cola signs to vintage postcards to 1950s sunglasses. And there’s plenty of costume jewelry. Arcadia has an old West feel, which makes sense because the twice-a-year rodeo brings lots of cowboys to town, real and not.

Miami, Brickell Neighborhood

The formerly staid financial district is dancing to a new beat with late-night joints for food and drink plus lots of new condo/apartment buildings on the rise. An upscale mall jammed with designer stores is a big draw for fashionistas and lookiloos, too. A smaller, tangle of shops at Mary Brickell Village even has a barbershop that can give you a trendy cut well into the night.

Miami, Calle Ocho

Officially known as Southwest 8th Street, Calle Ocho marks the epicenter of Miami’s Little Havana, whisking visitors into a Latin world flavored with rich coffees, fragrant rums, decadent Cuban cigars and tropical ice creams. On this one-way thoroughfare, murals bring history to vivid life; lively music spills onto the street and domino players test their skills in traditional, intense gameplay.

Miami, Ocean Drive

Stretched along the shimmering sands of legendary Miami’s South Beach, so close to the Atlantic you can smell the salt in the air, Ocean Drive dazzles the senses with neon colors, art deco buildings and a vibrance that infuses everything and everybody. There, you can see impossibly beautiful people nibbling breakfast outside at the Front Porch Café (is that who it looks like?); celebrate epic nightlife at the Clevelander, famed for the pool that marks the center of the its patio; and explore the Art Deco Historic District, encompassing the United States’ largest concentration of buildings constructed in this notable architectural style.

Palm Beaches

Looking for a sweet pink and green Lilly Pulitzer to take home as a souvenir? And one for a good price, too? The vintage shops of Palm Beach and West Palm Beach have you covered. The fashion plates of Palm Beach, long the winter playground for the wealthy, cast off their designer duds regularly and they wind up in stores on the barrier island and in neighboring West Palm Beach, along the Dixie Highway. This is the place to get a pair of barely worn Manolo Blahnik black heels.

Key West, Mallory Square

This cool block in Key West is actually a square. For decades, visitors have gathered each night to watch the sunset at Mallory Square. And before that happens, there’s a cast of characters that entertain the crowds with sword swallowing and serenading and feats of magic. While you wait, you can have your palm or tarot cards read, drink a tropical elixir from a coconut or just sit and watch the people. It won’t be long before you join the dance.

Key West, Duval Street

Duval Street in Key West, is a quirky, free-spirited place where roosters roam among the tourists and historic buildings, where normal concerns and decorum dissolve in the tropical breeze. A mere 1.25 miles long, Key West’s main drag is nicknamed “The Longest Street in the World” as it runs the entire distance from the Gulf of Mexico to the Atlantic Ocean. This stretch of pavement has rightly earned a reputation as party central with its menagerie of boisterous bars – a higher number per capita than any other place in the country -- but it’s more than that; it’s the beating heart of the Conch Republic, brimming with eclectic shops, art galleries, eateries and attractions.

Fort Myers

Sunsets are something to behold on Florida’s West Coast and the best place for a colorful selfie in the city’s River District is the river basin plaza. But before the sun disappears, wander through the shops in the historic area that have given the area new energy. River District food celebrates Florida differently than the usual beach joints. Sure, there are grouper sandwiches and the required burgers, but wild Florida hog and more unusual fare can be found here.


About 15 miles west of Fort Myers is Florida’s best-kept secret, a funky town called Matlacha. It’s just a few blocks long and flanked by Pine Island Sound on either side so you know it’s a hot spot for fishing and boating. There are enough art galleries, curio shops and restaurants to keep a visitor busy for an afternoon and a few spots to stay overnight if they are so inclined. Keep your camera ready since there are plenty of tropical backdrops for photos. The buildings are mostly painted pink, green and fun.

Punta Gorda

Hurricane Charley didn’t play nice with Punta Gorda when it roared through in 2004, but this resilient city has bounced back in surprising ways. A nighttime walking tour of the downtown core is a good time to listen to live music, especially on the weekends. Visitors can pull up a stool and listen to Margaritaville-type beach jams, Celtic favorites, current and classic rock at watering holes within a few. Start and end your excursion with a drink at the rooftop bar at the Wyvern Hotel.


A short stretch of Central Avenue north of the vibrant Rosemary District is a one-two punch of salvage nirvana. A visitor could easily spend half a day rummaging through Sarasota Architectural Salvage. Both inside and outside are stuffed with treasures that you might not know you needed including old doors and windows, vintage tin signs, pitchforks, lighting fixtures and more. Within walking distance is Circus City Architectural Salvage that has similar items but more circus related stock, including banners and vintage posters.

The cool blocks of Florida are a bonus to a Sunshine State vacation. They are another layer of what this interesting state is all about.