10 Most Eccentric Towns in Florida
Boasting an extensive array of island towns, unspoiled islands, and beach escapes, it is no wonder that the Sunshine State has long been among the US's top three most visited states. Despite rare hurricanes, sunny skies welcome tourists along the sun-kissed shores, gleaning off Gilded Age mansions and playing in the turquoise surf of the Gulf. Get hooked in Matlacha over local sights and fish-to-table cuisine sloshing around the town's islands.
Crystal River is home to gentle giants, playful manatees, and balmy springs. In St. Augustine, the oldest European settlement in the US along Florida's historic coast, you will discover a lighthouse, hidden courtyards, and Spanish-influenced architecture, including Castillo de San Marcos National Monument overlooking Matanzas Bay. These ten towns are a real standout among the overcrowded destinations.
Celebration
Just 25 minutes southwest of Orlando, Celebration is a picture-perfect community with a charged atmosphere. Founded more recently by none other than The Walt Disney Company in the 1990s, its idyllic downtown with architecture inspired by traditional Southern towns was named among the US's prettiest neighborhoods by Forbes. Celebrating life every day, it beckons visitors with Celebration Town Center's mix of boutique shopping and restaurants along the lakeside, brick-lined streets. Stroll, bike, or take in the scene on a horse-drawn carriage ride along Lake Richard. After a flavor-packed breakfast at Maple Street Biscuit Company or a delectable French pastry at Le Macaron, browse the jewelry, essential oils, and self-care products at Gypsy Moon Market.
This upscale suburb and a quirky town in one immerses you in nostalgic charm through a collection of unique architecture—more like a work of art than a residential area, including its Town Hall by Philip Johnson. Score accessories, toys, and collectibles at Market Street Gallery and fine-dine on Spanish and Cuban cuisine at the famed Columbia Restaurant. Celebration Hotel is an upscale boutique hotel five minutes from Walt Disney World, plus additional rooms through the Kissimmee area. Perfect for a chill getaway before the holidays, with stores full of gifts, gourmet food, clothing, and home decor, stop by the Googie Style Cinema by Cesar Pelli, among other family-friendly amenities like Town Tavern, Nature's Table and Hotel by Graham Gund.
Cortez
Just west of Bradenton, Cortez exudes Old Florida vibes as one of the only remaining authentic fishing villages on the Southwest Coast of the state. This is a place for saltwater fun and indulging in seafood served any style in homey digs. From pirate ship cruises to watersports and annual events, your whole family will find something engaging while paying tribute to the community’s maritime heritage, a vital role in Florida's fishing history. The downtown is a blur of locals mingling between shops and restaurants, with local tour operators and rental companies offering boat, jet ski, and paddleboard rentals. Founded by families from North Carolina in the 1880s, its Bratton/Burton Store is the first commercial building in the village.
Take a stroll along the working waterfront and marinas, with fresh-caught seafood being hauled, or charter your own catch to fry up by the beach, sailing among fishing boats. Get insights on local architecture with the Cortez Village Walking Tour, including Cortez Cultural Center, a community hub that celebrates local art and history through events. The Florida Maritime Museum is a brick, circa 1912 schoolhouse. Just across the Cortez Bridge on Anna Maria Island, Cortez Beach offers 140 feet of pristine shoreline lapped by the turquoise Gulf surf. From the Cortez Stone Crab & Music Festival in November to the Cortez Commercial Fishing Festival in February, the Florida Maritime Museum hosts the Cortez Nautical Flea Market in March, with fishing and nautical gear, plus coastal arts and crafts.
Crystal River
Most known for its comical manatees, this sweet town promises a magical escape for the entire family along the Gulf Coast. Discover Florida’s warm and playful soul amid spring-fed rivers, home to the gentle giants, plus great fishing and bountiful lakes. The Crystal River Preserve State Park comprises 20 miles of coastline with islands, inlets, and trails for wildlife viewing, plus a visitor center. Swim with the animals in Three Sisters Springs, where in the winter, manatees can be viewed from a boardwalk in the clear water of this refuge. Browsing local shops and businesses, you will discover local restaurants and accommodations, like the Biscuit Barn and the visitor center next to American Pro Diving Center-Swim With Manatees.
Despite recent hurricanes, the Citrus County communities have shown incredible resilience in maintaining some of America’s top cycling trails, parks, and attractions. Take the Eco-Walk Trailhead or kayak and make your way over to the tip of the mangroves known as the blissful Fort Island Beach, with covered picnic tables and amenities along pearly sands, plus a boat ramp and a fishing pier. You can take advantage of Paddles Outdoor Rentals and Tours, dive for scallops, and taste fish-to-fork cuisine. Stop by Lollygaggers and catch the sunset from the dog-friendly Kings Bay Park, just a stroll away. You will meet friendly folk who live a paced life like the animals in the balmy springs.
Dunedin
This good-looking town owes much to its Scottish roots, once settled along these pristine shores and white sand beaches of the Gulf Coast. Just 30 minutes west of Tampa, an escape to Dunedin, an official trail town, means miles of walking and biking paths, a lively, bike-friendly downtown of quaint shops, craft breweries, and independent eateries, plus its two unspoiled island state parks. Equal parts atmospheric and kitschy, just rent a bike and see where the trails take you. Both the seasonal Caladesi and Honeymoon Islands are beach havens, with trails like Mangrove Shell Tree and Osprey Trailhead; Honeymoon Island also features a pet beach. You can take a charter for unique deep-water varieties or hit the surf with a paddleboard.
The city pier is perfect for fishing and strolls, local life, and sunsets, while the Dunedin Museum offers invigorating history. Tourists can imbibe spirited heritage along bright-hued buildings, giving a nod to the Scots through old shops and craft beer pubs, stop by for a local event, and see the spring training home of the Toronto Blue Jays. Don't miss exhibits at Stirling Art Studios & Gallery, the Dunedin Downtown Market, and Josiah Cephas Weaver Park with a playground. The 45-mile paved Fred Marquis Pinellas Trail extends from St. Petersburg to Tarpon Springs. Sample the local fare at Bon Appétit Restaurant & Bar on the water with an outdoor bar, saving room for Strachan’s Ice Cream & Desserts before the sunset from Dunedin Marina and your slumber at Hampton Inn Dunedin.
Matlacha
Call it preppy, perky, or quirky—the beauty of this town is one of a kind. A visit to Matlacha, pronounced 'MAT-la-shay,' meaning 'water to the chin' in the Calusa language, lifts your soul with gift shops, art, and opportunities to play. Having begun after pacing off building lots east of the bridge across Matlacha Pass, this pea-sized town just off mainland Cape Coral is where the kids canoe from their backyards and catch three-pound sea trout. You’ll spot locals with fishing hooks tucked in their shirt pockets and others sporting shin-high white rubber boots. Whimsy bubbles up like champagne in Matlacha, with no shop higher than a tall tree.
Get "Matlacha Reeboks" for yourself because sloshing around the fecund waters of the town's islands is fun. From fishing tournaments to paddling around the islands, it is as much about the pace in this watery angler's paradise—and the calmer you are, the more they will bite. Take a fishing charter with guides throughout, stop by the town hall, and taste the local bounty from one of the fish shacks, and you'll be "hooked," too. Blue Dog Bar & Grill is an upbeat watering hole featuring American grub, seafood, and drinks on the water. A friendly chat with owners, the enticing bridge, outrageous mannequins, polka-dot dolphins, and coconut postcards—every moment feels photogenic.
Micanopy
Just 10 miles south of the bustling Gainesville, Micanopy is an Old Florida town draped in Spanish moss, with old-growth magnificent oaks along the main street. It's easy to feel part of the "crowd," with weekend visitors flocking in to shop and soak up old-fashioned charm along the historic storefronts of Cholokka Boulevard. From Antique City Mall to Wren Wood Antiques and Delectable Collectibles, score a sought-after Florida Highwaymen painting at Micanopy Outpost and a gift for a friend at JEMsOriginals. Sifting through treasures, the "Shop" offers vintage and modern home decor and art to remember this antiqued town. Sweets, delicious deli foods, and tasty sit-down eateries line both ways from your charming stay at the circa-1845 Herlong Mansion Bed & Breakfast.
Between a morning jolt from Coffee N’ Cream and dinner at Blue Highway Pizzeria, discover Micanopy’s 200-year history at Micanopy Historical Society Museum and Micanopy Historic Cemetery. It is just a hop to the short and easy hiking trails of the Native American Heritage Preserve and Tuscawilla Preserve. To the north, Paynes Prairie Preserve State Park boasts bison and wild horses in their natural habitat, while 10 miles east, Cross Creek and Marjorie Kinnan Rawlings Historic State Park flaunt Cracker-style homes and 1930s-era farms of the Pulitzer Prize-winning author of “The Yearling.” For a full Micanopy experience, take a stroll through the nearby Barr Hammock Preserve, dine at The Yearling Restaurant, and don't miss Mosswood Farm Store and Bake House to bring goodies back.
St. Augustine
Dating back to 1565, St. Augustine, the oldest European settlement in the continental US, is also among the state's most exuberant towns, recently named one of America's most romantic cities. With haunted whispers in between those 1700s buildings and romance in the air, the Spanish-settled town inspires on a stroll with its hidden courtyards and the sound of horses trotting on its brick-paved streets. Admire the riverfront architecture on a stroll to the ocean views in between many attractions and tours. The Medieval Torture Museum gives it a unique edge. From popular horse-drawn carriage rides and cruises, take advantage of the Lighthouse Park Boat Ramp, perfect for kayaking, fishing, and paddleboarding.
The not-to-miss Augustine Lighthouse & Maritime Museum offers climbing tours of an 1874 black-and-white striped lighthouse, plus a shipyard playground. Even a short visit will give you a unique perspective into simpler times, but it wouldn't be complete without the natural experiences at Anastasia State Park and Matanzas State Forest. The coarse-sanded Anastasia Beach is wonderful for relaxing the mind and body. Nearby, Castillo de San Marcos National Monument is a historic fort offering self-guided tours of the drawbridge and the gun deck set against Matanzas Bay views. After a stop at a distillery for a chat with the local folk, you can take a walking nightly tour or be tucked in your bed at a romantic accommodation like those overlooking the bay.
Steinhatchee
Some 70 miles west of Gainesville, the Steinhatchee is a prime destination for seafood lovers and outdoor enthusiasts. Encapsulating rich Gulf history, the area, inhabited since at least 12,000 BC, was home to Timucua and Seminole tribes, with the name derived from “Esteen Hatchee,” or “River of Man.” Steinhatchee, also “The Best-Kept Secret in Florida,” offers access to the Steinhatchee River and the Gulf of Mexico, abundant in sought-after varieties like grouper, snapper, redfish, spotted sea trout, black sea bass, and tarpon. Many enjoy scalloping in the summer as a family-friendly pursuit to wade in the shallows. The Steinhatchee River Paddling Trail offers a six-mile tour from Steinhatchee Falls to the Jena Boat Ramp, while the Fiddler Crab Festival is upcoming in February. Rent a boat or charter a fishing trip when you stop by for Sips and Sunsets next November.
Deadman Bay and the Steinhatchee River were significant for Spanish conquistadors, like Pánfilo de Narváez and Hernando de Soto, who navigated these shores in the early 1500s. In 1931, the community took on the name of the area from its previous name, Deadman Bay, linked to incidents involving early settlers. Explore the remnants of salt works from the Civil War era—essential during the Confederacy—plus the 1838-built Fort Frank Brooke, which protected settlers through the Second Seminole War. Preserving its character in charming buildings and laid-back marinas, find a stay among quaint cottages, resorts, and inns, like Steinhatchee Landing Resort, with stunning views of the water. Among the foodies' hotspots, Kathi’s Krab Shack and Fiddler’s Restaurant & Resort serve fresh seafood, while the bright and beachy McDavid’s Cafe fries up hot donuts and Southern-style brunch.
Tarpon Springs
Tarpon Springs, one of the most whimsical small towns in Florida, celebrates its rich Greek heritage every day. Known as the “Sponge Capital of the World,” it ties historical roots with contemporary local culture, making for a one-of-a-kind Sunshine State experience. Just 30 miles from Tampa and 30 minutes north of Clearwater on Florida’s Gulf Coast, many come for the Mediterranean feel along Dodecanese Boulevard. Strolling along its buildings and businesses, you will discover unique history through sites like the Tarpon Springs Heritage Museum and Saint Nicholas Greek Orthodox Cathedral. The food, festivals, and the famous sponge docks add to the town’s distinctive quirks.
For an in-depth experience, a self-guided audio walking tour through the Greektown Historic District begins near the famous docks with sponge boats, with ten stops. Get the inside scoop on the traditional sponge harvesting industry with demonstrations and a variety of specialty shops, plus enjoy your own wanderings for authentic Greek food through local stores. Many family-owned restaurants are waterfront and harken to the vibrant roots, including Tarpon and Dimitri's on the Water. The paved, 47-mile Fred Marquis Pinellas Trail is perfect for biking and hiking. Take your adventures further via a ferry ride three miles off this coast to Anclote Key Preserve State Park, which is only accessible by boat.
Winter Garden
Another whimsical name in the Sunshine State, Winter Garden is a delightful small city on the southern shore of Lake Apopka with unique events like the Health & Harvest Festival and the All-American Kids Parade & Breakfast. Its artistic edge lends an eventful ambiance of festivals and community gatherings, plus small-town attractions like the Garden Theater, which opened in the 1930s. Tucker Ranch Recreation and Nature Complex spans over 200 acres of walkable and hikeable trails. Stop by the pet-friendly Chapin Station, a park with a playground, and shop at Plant St. Market, a community vendor ground with 20 local sellers. Miller's Ale House is a casual sports pub chain with bar snacks, steaks, and a large selection of beers on tap.
This small city combines the best of worlds as the cultural capital of Orange County, surrounded by nature preserves and dense wilderness areas. Just north along the shore, Magnolia Park features a campground, a butterfly garden, and bike paths in an engaging, family-friendly space with roaming peacocks. From West Orange Trail to Butterfly Garden - WO Trail, Newton Park is a popular lakefront spot with a playground, boat launch, covered picnic pavilion, and fishing pier. Come anytime for Florida’s founding history through the beautiful historic district, with a stop by the Central Florida Railroad Museum and Winter Garden Heritage Museum. The annual Craft Affair is a great reason to plan a trip in November.
Experience Florida's Most Unique and Photogenic Towns
Each sun-drenched town in Florida offers its own unique character, set against the state's varied and picturesque landscapes. From the centuries-old charm of St. Augustine, with its brick-lined streets and hidden courtyards, to the vibrant art scene in tiny Matlacha, these towns celebrate Florida’s beauty and quirky appeal in ways only they can.
While the glitz of Miami and Orlando’s resorts will always attract first-time visitors, exploring these offbeat and historic places reveals a Florida rich in local flavor, history, and tight-knit communities. Whether you’re seeking coastal views, a taste of Old Florida, or a lively town square, these destinations invite you to uncover their charm in memorable ways suited to all ages and interests.
