Dubbed the “Athens of Florida”, DeLand was founded by wealthy businessman Henry A. DeLand in 1876, who wanted the city to embody the culture, education and beauty of the Greek capital. With its red-brick buildings and oak-lined streets, its charm may be more New England than Ancient Greece, but there are plenty of cultural and historic hot spots. Here you’ll find Florida’s oldest college, Stetson University, named after famous hatmaker and donor John B. Stetson. There’s also the 1920s-era Athens Theatre, the colorful Mural Walk, plus record stores, antique stores and independent breweries.
With its laid-back and friendly atmosphere, Niceville certainly lives up to its name. Located in the western panhandle between Pensacola and Panama City, this dinky city has a population of around 12,500. As well as being an ideal base for exploring the white sandy beaches of Destin, a 20-minute drive away, Niceville has plenty of attractions of its own. These include the nature trails of Turkey Creek Park and the Mattie Kelly Arts Center, which has two galleries and showcases performances year-round.
The striking red beacon that crowns Ponce Inlet has become a symbol of the town. Built in 1887, at a height of 175 feet (53m) it’s the tallest lighthouse in Florida, as well as being considered one of the best-preserved historic light stations in the country – it’s one of just 11 recognized on the National Historic Landmark list. The town is just as gorgeous at ground-level too. A fishing hub in past and present times, it has several attractive marinas and shipyards, as well as oceanfront restaurants serving up the catch of the day.
The quaint city of Chipley is tucked away in the panhandle between Tallahassee and Pensacola. Despite being a small community of just 3,600, it has a vibrant cultural life and plenty of natural beauty. One of the biggest draws is Main Street Market, a bustling farmers' market filled with the best local produce, from fresher-than-fresh oysters to seasonal fruit and vegetables. Just three miles (5km) south of Chipley is Falling Waters State Park (pictured), home to fern-draped landscapes thronged with native butterflies, as well as Florida's tallest waterfall.
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Located in southeastern Florida’s Treasure Coast region, Vero Beach has been nicknamed the Hamptons of Florida: it’s where the well-heeled go for a little rest and relaxation. The palm-fringed paradise is the perfect location for trendy bars, boutiques and restaurants. Vero Beach started life as a citrus farming region and today Schacht Groves, a fourth-generation business, offers visitors the chance to learn about the history of fruit growing here and taste its bounties for themselves.
When it comes to old-school charm, Mount Dora ticks all the boxes. Situated in central Florida around a 45-minute drive from downtown Orlando, the quaint city is an enticing combination of antique stores – which draw in enthusiasts from all over the world – outdoor cafés, galleries and historic gems. Its best-known building is the Lakeside Inn, Florida’s oldest continuously operating hotel, which was constructed in 1883 and remains popular today.
Known as the “Sailfish Capital of the World”, the waters around Stuart are swarming with these blue-and-silver finned fish. The town in Martin County, southern Florida is said to have gained its moniker in 1938, after a team of journalists came to visit and caught more than 1,000 sailfish in under a week. Aside from its glistening azure waters, Stuart is known for its former silent movie theater turned performing arts center, The Lyric, which was opened in 1926. Its uncluttered downtown wears its laid-back attitude on its sleeve: think low-rise buildings, a smattering of upscale boutiques and restaurants and a weekly farmers' market.
Key Largo is often the first stop for those visiting the Florida Keys – it’s the northernmost and longest of the islands. While it’s a popular destination, Key Largo’s year-round residents number around 10,000 and it still retains much of its easy-breezy, small-town feel. It’s known for having the world’s second-largest artificial reef, created by the sinking of ships off the coast, which means there are ample opportunities for diving here as well as snorkeling, fishing, kayaking and paddleboarding.
The red-brick streets of Winter Park look like they’re made for lazy strolling. Although it’s just a 20-minute drive northeast of Orlando, this leafy city with a suburban feel is a world away from Disney’s homeland. It has a thriving food scene, with acclaimed restaurants serving everything from sushi and seafood to classic American fare, plus there’s a farmers' market every Saturday. Natural beauty is never far from these streets either: Winter Park has a chain of lakes and canals which can be cruised by boat tour.
Boca Grande has bucketloads of Old Florida allure. Situated on Gasparilla island, off the Gulf Coast, the town has certainly earned name-dropping rights, having been graced by the likes of Henry Ford, JP Morgan, the Bush family and Audrey Hepburn in its 100-plus years as a tourist destination. It was put on the map in the 1880s after railroads were built into the area, shortly after which wealthy visitors began to trickle in from the North. One of its main draws in past and present times is the Gasparilla Inn & Club, completed in 1911, a luxurious manor that still retains every inch of its timeless glamor.
A village with a difference, Islamorada is spread across six islands that sit between the Everglades National Park and Florida Strait. It’s the epitome of a tropical paradise: think shimmering turquoise waters, swaying palms and some 1,200 feet (366m) of stunning beaches. Regarded as the “Sportfishing Capital of the World”, Islamorada’s crystal-like seas are teeming with sailfish, permit, tarpon, redfish and bonefish (to name a few), plus it’s reputed to have the largest fishing fleet per square mile on the planet.
This Gulf Coast gem is the perfect place to step away from the crowds and embrace laid-back waterfront living. Surrounded by the stunning Charlotte Harbor, which curves its way inland along Florida’s west coast, Punta Gorda is a popular spot for sailing, fishing and a range of watersports. Despite being badly damaged by Hurricane Charley in 2004, its historic district, made up of late-19th and early- 20th century buildings, has been carefully restored and gives a glimpse into Punta Gorda’s beguiling past.
St. Petersburg owes much of its recognizable Mediterranean Revival architecture to the Sunshine State's boom of the 1920s, when an influx of new residents moved to Florida. During this time, the city gained many of its most notable buildings, including the opulent Don CeSar Hotel or “Pink Palace”, which was frequented by F. Scott Fitzgerald in its heyday. It holds a few modern-day accolades too: St. Pete Beach was voted the best in the US by TripAdvisor in 2021; it also holds the Guinness World Record for the most consecutive days of sunshine at a whopping 768.
Situated in the panhandle against the Gulf of Mexico, Destin’s pristine white beaches owe their trademark hue to tiny crystals of Appalachian quartz, which washed in during the last Ice Age. Yet there’s plenty more to discover besides: from fishing in clear waters to eating fresh seafood in local restaurants, or taking a peek at the luxurious condos lining the shore. Despite being a popular resort, Destin’s permanent population is small at just 13,000 and the town has kept its friendly, community feel.
Just off the west coast of Florida, around 50 miles (80km) south of Tampa, Anna Maria Island is a tropical treasure with something for everyone. There are its jaw-dropping beaches, ranging from the wide expanse of central Holmes Beach to the rugged, secluded Coquina Beach on the south side. Then there’s the historic Bridge Street, with a mix of independent shops, restaurants and galleries. The jewel in Anna Maria Island’s crown, though, is its pier. Completed in 1912, it contains more than 1,100 unique engraved planks dedicated to locals and their loved ones, although it was badly damaged by Hurricane Irma in 2017 and is currently being rebuilt.
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Venice holds the somewhat unusual title of “Shark Tooth Capital of the World”. Roughly 10 million years ago, Florida was submerged underwater and sharks were native to the area, but as the water gradually retreated the animals died, and all that remains today are their fossilzed teeth. As well as attracting fossil-hunters, the town brings in visitors of all stripes thanks to its charming Italian Renaissance-style downtown, unspoiled Gulf Coast beaches and around 30 miles (48km) of panoramic bike trails.
While it’s technically part of the city of Miami, Coconut Grove moves to the beat of its own drum. This laid-back neighborhood started life in 1873, when an eclectic mix of artists, writers, pioneers and adventurers moved to the area, lending it the bohemian character it’s known for today. With its buzzy outdoor bars and cafés lining its streets, as well as plenty of luxurious yachts dotted along its harbor, “The Grove” as it’s known by locals, has earned a reputation as a hip neighborhood with a village-like feel.
Picturesque Sebring is a mecca for outdoor enthusiasts. Located on the dreamy shores of Lake Placid in central Florida, surrounded by Cypress swamps and sand pine scrubland, it’s the perfect backdrop for a range of activities from hiking and cycling to watersports. It’s also been dubbed the “City on the Circle” thanks to the unique circular design of its streets, designed around the central Circle Park. Adding another feather to its cap, the town is home to Sebring International Raceway, a former Second World War base turned car racing track that hosts the annual 12 Hours of Sebring event.
The last of the Florida Keys, located on a dinky four-mile (6.4km) long, two-mile (3.2km) wide island, Key West is a sun-drenched beach town with a lot going for it. The crystal-clear waters that surround it are a haven for scuba diving, sailing and snorkeling, while there’s plenty to see on dry land too. Its compact downtown is a patchwork of palm-fringed streets lined with pretty conch-style houses, seeped in the histories of famous names who once vacationed here, from Ernest Hemingway to Tennessee Williams.
Colorful beachfront cabins such as this one are a common sight in Matlacha. Located on a small spit off the coast of Fort Myers, the hamlet is painted in a rainbow of unashamedly bright hues. It started life as a fishing village but in the 1990s, when it became clear that the dwindling fishing industry wasn’t enough to support all residents, locals took to the paint palette to revive the town and attract tourists. Inside these vivid buildings you’ll find art galleries, beach bars, independent restaurants and more.
Seen from the skies, Grayton Beach is a winning combination of pristine sands and almost fluorescent turquoise seas. Situated in the panhandle about halfway between Pensacola and Panama City, the town is mostly covered by the 400-acre Grayton Beach State Park, with landscapes including everything from pristine beaches to windswept forests. As well as exploring its jaw-dropping scenery, visitors can stroll through the town’s quaint white-picket-fence communities or pop into a waterfront restaurant for a taste of Southern cuisine.
Sanibel Island is completely show-stopping at sunset, when its seaweed-dappled shores are painted an array of pastel hues. Located west of Fort Myers, the 15-mile (24km) long, five-mile (8km) wide island is crowned by the 19th-century Sanibel Lighthouse, which remains in operation today. But that’s not the only treasure to be found in this small city. Known for being home to a wide range of seashells, Sanibel Island’s beaches are so popular with shell-hunters that hotels provide special facilities for sorting and cleaning them, while there's even a dedicated museum here containing the world's largest shells.
Taking the top spot in our round-up is Naples, a tropical charmer on the Paradise Coast. Of course, it’s home to the sugar-sand beaches you’d expect from this stretch of coastline, but the city itself is just as striking too. The historic streets of Third Street South and Fifth Avenue South are the perfect eye candy, their pastel-hued buildings decorated with cascading blooms, providing a unique location for the upscale shops, bars and restaurants which you’ll find there today.
Cute-as-a-button Seaside attracts visitors for – you guessed it – its stunning beaches. Located in the panhandle between Panama City and Fort Walton Beach, it’s home to nine unique pavilions leading down to the shore, each designed by a different architect. But there’s plenty to discover aside from the stunning coastline: think independent bookstores and record stores, farmers’ markets, art galleries and theaters.
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