Ranked: Florida’s most beautiful small towns and cities
Sunshine State spots with plenty of charm

America’s southernmost state might be best known for bustling resorts like Miami and Orlando, but beyond the bright lights and big cities there are plenty of smaller places worth exploring too. What they lack in size, these coastal charmers and quaint historic towns more than make up for in beauty. Using reviews from Tripadvisor, plus knowledge from our own expert team of travel writers, we've ranked our favourites.
Scroll on to see how we've ranked Florida's most beautiful small towns and cities...
34. Madison, Madison County

Known for its winning blend of Victorian homes and historic buildings, this small city near Florida's central northern border catches the eye and steals the heart. Notable landmarks here include the Four Freedoms Monument, with its historic connection to a speech by President Franklin D. Roosevelt, and the Dial-Goza House (pictured), an idyllic 19th-century mansion built for a Confederate veteran of the American Civil War.
Every spring, Madison sparks into life during the Down Home Days Festival. It's an event that's all about community, with locals coming together to enjoy a parade, arts and crafts, family-fun activities and traditional Southern cooking.
33. Dade City, Pasco County

If you think antique shops mixed with rolling hills and Southern hospitality sounds like a winning formula, you'd be right – it is. Situated in Central Florida, Dade City is the kind of charming place that pulls in visitors year-round but it's especially busy during the annual Kumquat Festival. As its name suggests, it's an event that celebrates the small and tart citrus fruit that grows so well in the Sunshine State.
Once they've had their fill of kumquats, history buffs should head for the Pioneer Florida Museum and Village to learn about the area's rich heritage and early settlers. Feeling hungry again? Head to Kafe Kokopelli for casual fine dining in a unique atmosphere.
32: Cedar Key, Levy County

Come to sample the rugged and scenic Nature Coast, stay for the charming Old Florida architecture and relaxed way of life. This, in a nutshell, is what Cedar Key – a family-friendly destination where fishing, boating and taking it easy are top priorities – is all about.
From exploring the Cedar Keys National Wildlife Refuge, with its 13 islands that were once home to camps used by First Peoples, to soaking up sunsets with walks down at the marina, this place has plenty to offer. While you're here, be sure to check out Cedar Key Museum State Park and Cemetery Point Park. And, of course, don't skip town before tasting the famous clam chowder at Tony's.
31: Chipley, Washington County

The quaint city of Chipley is tucked away in the panhandle between Tallahassee and Pensacola. Home to a population of just under 4,000 people, 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 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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30: Winter Park, Orange County

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.
29: Islamorada, Monroe County

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 stunning beaches.
Regarded as the 'Sport-fishing 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.
28: Coconut Grove, Miami-Dade County

While it’s technically part of the city of Miami, Coconut Grove moves to the beat of its own drum. This laid-back neighbourhood 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 harbour, The Grove, as it’s known by locals, has earned a reputation as a hip spot with a village-like feel.
27: Destin, Okaloosa County

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 14,000 and the town has kept its friendly, community feel.
26: Apalachicola, Franklin County

A dainty maritime town on the Gulf of Mexico, Apalachicola is brimming with historic charm. In fact, it’s recognised by the National Trust for Historic Preservation as a 'distinctive destination' thanks to its well-preserved buildings, some of which date to the early 1830s.
These include former ships’ chandleries, warehouses and factories, with many transformed into trendy bars, cafés, restaurants and galleries, making the city a seamless fusion of old and new.
25: Matlacha, Lee County

Colourful 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.
24: Tarpon Springs, Pinellas County

Tarpon Springs takes its name from the fish which populate its surrounding seas – but they’re not the only thing that’s abundant here. In the early 20th century, Greek settlers discovered plentiful natural sponge in these waters and set up a thriving industry selling the stuff.
Today, the town’s Greek influence can be seen in its whitewashed buildings, narrow winding streets and markets selling Mediterranean foods. Plus of course, there’s plenty of stores that sell natural sponge to take home.
23: Sebring, Highlands County

Picturesque Sebring is a mecca for outdoor enthusiasts. Located on the dreamy shores of Lake Jackson 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, focused around the central Circle Park. Adding another feather to its cap, the town is home to the Sebring International Raceway, a former World War II base turned car racing track that hosts the annual 12 Hours of Sebring event.
22: DeLand, Volusia County

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 hotspots.
Here you’ll find one of Florida’s oldest colleges, Stetson University, named after famous hatmaker and donor John B. Stetson. There’s also the 1920s-era Athens Theatre, the colourful Mural Walk, plus record stores, antique stores and independent breweries.
21: Niceville, Okaloosa County

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 16,000.
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.
20: Ponce Inlet, Volusia County

The striking red beacon that crowns Ponce Inlet has become a symbol of the town. Built in 1887, up to a height of 175 feet (53m), it’s the tallest lighthouse in Florida and is considered one of the best-preserved historic light stations in the country.
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.
19: Vero Beach, Indian River County

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.
18: Crystal River, Citrus County

In cooler months manatees flock to the balmy natural springs around Crystal River, a small city that’s roughly a 90-minute drive north of Tampa on Florida’s west coast. Aside from swimming with these beautiful creatures in their natural habitat – at the only place in the US where it’s legal to do so – tourists can swim in the crystal-clear waters of the springs, or enjoy paddleboarding or kayaking.
17: Fernandina Beach, Nassau County

Fernandina Beach is a beguiling seaside town with a colourful past. It’s located on Amelia Island on Florida’s northeastern coast, which is the only place in the US that has been under the control of eight different national regimes, earning it the nickname of 'Isle of Eight Flags'.
The 50-block downtown region, recognised as a National Historic District, delights visitors with a diverse mix of boutiques, well-preserved Victorian architecture, galleries and museums.
16: Mount Dora, Lake County

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.
15: Stuart, Martin County

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 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 theatre turned performing arts centre, The Lyric, and its uncluttered downtown, boasting low-rise buildings, a smattering of upscale boutiques and restaurants and a weekly farmers' market.
14: Key Largo, Monroe County

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 14,000 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 snorkelling, fishing, kayaking and paddleboarding.
13: Boca Grande, Charlotte and Lee Counties

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 is the Gasparilla Inn & Club, completed in 1911, a luxurious manor that still retains every inch of its timeless glamour.
12: Punta Gorda, Charlotte County

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.
11: St. Petersburg, Pinellas County

St. Petersburg owes much of its recognisable 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 is often voted among the best in the US; it also holds the Guinness World Record for the most consecutive days of sunshine at a whopping 768.
10: Dunedin, Pinellas County

With its colourful buildings and kitsch Jolley Trolley trams that cruise the streets, Dunedin has postcard-perfect good looks. Bringing a touch of Scottish charm to the Gulf Coast, the town was settled by the Scots in 1852 and takes its name from the Gaelic word for Edinburgh, Dun Eideann.
Street names such as Highland Avenue and Scotland Street nod to this heritage, while festivals including the Dunedin Celtic Music and Craft Beer Festival are a full-blown celebration of Scottish culture.
9: Anna Maria Island, Manatee County

Around 50 miles (80km) south of Tampa, Anna Maria Island is a tropical treasure. There are jaw-dropping beaches, ranging from the central Holmes Beach to the secluded Coquina Beach. 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.
8: Venice, Sarasota County

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 fossilised 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.
7: Key West, Monroe County

The last of the Florida Keys, located on a dinky four-mile-long (6.4km), two-mile-wide (3.2km) 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 snorkelling, 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 holidayed here, from Ernest Hemingway to Tennessee Williams.
6: Grayton Beach, Walton County

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.
5: Sanibel Island, Lee County

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-long (24km), five-mile-wide (8km) 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.
4: Naples, Collier County

Naples is 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.
3: Seaside, Walton County

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 theatres.
2: St Augustine, St. Johns County

Cobbled streets and centuries-old Moorish and Spanish colonial buildings make up the famous Historic District of St Augustine. This northwest coast gem is the oldest continuously occupied European settlement on the continent, with the Spanish explorer Juan Ponce de Leon arriving here in 1513.
As well as providing much for history buffs to enjoy, the city enchants all who visit with its jaunty orange-and-green Old Town Trolleys, quaint street cafés and hidden courtyards.
1. Micanopy, Alachua County

Just 10 miles (16km) south of Gainesville's hustle and bustle sits Micanopy, a small town that couldn't be more Old Florida if it tried. Home to fewer than 1,000 residents, it's a place where magnificent oak trees draped in Spanish moss line the historic main street, Cholokka Boulevard, and visitors can enjoy a slower pace of life.
Once you've bagged some bargains in the town's beautiful antique shops and indulged in some sweet treats at one of the cafés, head for the Micanopy Historical Society and Micanopy Historic Cemetery to learn more about the town's 200-plus years of history. If you ask us, towns in Florida don't come prettier than this one here.
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