11 Must-Visit Small Towns in Florida
Who doesn't dream of a Florida escape or a vacation? The Sunshine State is a worldwide destination; even Floridians enjoy vacationing in its small towns. Under the same sunny vibes and along the same coastal stretches of sugary sands, these small towns speak volumes to families, couples, and friends on a road trip looking to bond over unique experiences and nature.
Just look at Everglades City, immersed in wilderness, or the humble fishing village of Cedar Key, or Rosemary Beach, just off of Scenic Highway 30A. We're talking brick-paved streets, trolley rides, and lighthouses galore, and then off to the sunset on a cruise you go! Pastel cottages, welcoming inns, cute cafes—it doesn't get more quaint, personal, and yet exciting than these must-visit towns in Florida!
Anna Maria Island
The barrier island between the Gulf of Mexico and mainland Florida is a must-visit for every taste and state of mind, in any season. Whether you've been dreaming of a romantic escape or wiping your city slate clean, it just doesn't get better than here, with no high-rises, obstructed views, or construction noises. With a name that rolls off your tongue like honey, the little island town, a slice of heaven indeed, emanates peaceful vibes of relaxation upon approach. Anna Maria boasts seven pristine miles of white-sanded beaches to dive straight into waters or bury your toes into the soft, loungeable sands and let the worries go at the views!
The laidback downtown area, where you can truly relax, offers a step back into the Old Florida feel, with a quaint scene of antique stores and art galleries in between your finger-licking obsessions. From seafood delicacies to the wooden City Pier for a stroll into the sunset circa 1911, you must take the free trolley tour around town. Now that you've covered the basics, you can enjoy kayaking, stand-up paddleboarding, or simple beachy pleasures while spotting bottlenose dolphins. There is also great fishing, and bird lovers rejoice, having found their personal paradise on Anna Maria Island, a bird sanctuary!
Apalachicola
Ah, this lovely town that is so much fun to say is a definitive item on your Florida bucket list! Right on Apalachicola Bay in the Gulf of Mexico, the idyllic "Old Florida" destination awaits with the moniker of the oyster capital of the world and one of the best towns in the US to enjoy fresh seafood! Oh, and there is no better time to experience it all and then some than the annual, most-popular Florida Seafood Festival! Truly, a big name around the coast in fishing culture, and with bottomless maritime and oyster fishing, you will be happy discovering it for days!
But then again, come at your convenience for strolls through the Apalachicola Historic District, with its over 900 buildings—many dating nearly two centuries back! The sun and outdoors prevail here, with acres of national and state forests, so skip into Apalachicola National Forest and Tate's Hell State Forest, or take a trip to St. George’s Island for some big game fish while the little ones paddle in its protected shallow bays! The beautiful beach town with its own lovely waters running warm and clear offers a crowdless atmosphere to indulge in your favorite way!
Captiva Island
The town right off the mainland in the Gulf of Mexico is the ultimate destination for all types of outdoor lovers on a remote escape you've been dreaming of! Captiva captivates with a peaceful, beautiful island setting where all you want to do is bike through town with no traffic lights when not beachcombing for those marvelous shells. But then again, there's always fishing, sailing, and hiking to explore the outdoors in your favorite way with only those who matter! With its northernmost two-mile portion housing the South Seas Island Resort, you can stay here in luxury by the 2.5 miles of beach or come for the calendar-full of family-friendly events!
Explore the rest of the island on a bike ride with photo-worthy ops around each corner of the pastel-colored buildings, like the Bubble Room, a multi-themed restaurant and a definitive must-try at dinner! You can, no, you should take the bridge over Sanibel, which is no less captivating than its sister island on Florida's southwest coast and offers more biking, sailing, birding, and a variety of water activities. Its most varied tropical topography is characterized by giant cacti, bougainvillea vines, and the most stunning sunsets of your life!
Cedar Key
When it doesn't get smaller than Cedar Key, you know you've hit the jackpot for a second-to-none escape. The charming town "on stilts" suspended over the Gulf of Mexico, like ladies snatching up their skirts in fear of getting wet, is renowned for clamming. A must-visit town with just over 700 locals, it offers enough sights and experiences for a vacation and a do-over! There is no better clam chowder than there, where the people are warm like the climate and the town's history runs deep. The humble fishing village with multilevel houses of mom-and-pop stores encourages you to savor each succulent moment of the slow-paced lifestyle, like at an on-the-water restaurant!
A low-key hideaway of the state in the Gulf of Mexico, its swampy region is fun on a boat tour, while the sunsets are irreplicable, especially after a hike through the waterfront Waccasassa Bay Preserve State Park to come out for views! From the cutest annual rubber duck race in the fall to the popular RV park for a budget holiday stay, Cedar Key is a good, old-fashioned destination. You can get back to the town basics on a paddle around Cedar Keys National Wildlife Refuge and explore artifacts depicting the area's history as a busy port at Cedar Key Museum State Park.
Dunedin
Dunedin, one of the state's oldest towns, is a remarkable example of Old Florida. Together with its distinctive beaches and Scottish roots, founded by two Scotsmen in 1899, the mix lends itself to a unique local spirit with one-of-a-kind experiences, like its many Scottish festivities. The annual carnivals throughout the year greet you with an alive and kicking-it-up vibe that pulls you right in! Give into the relaxed feel and all your urges to shake off days behind a work desk during the fun Dunedin Highland Games in April.
Just an hour from Tampa, the charming downtown core is a walkable, significant attraction on its own, with popular craft breweries just a hop away from the four-mile-long Honeymoon Island beachfront. Among the two prominent state parks here, Honeymoon Island State Park offers gorgeous beaches and pine forests, as well as wildlife like owls, osprey, and woodpeckers. The 38-mile-long trail is great to take a bite out of on a morning stroll or cover the whole distance on a paddle ride. You can get back to lounging on the beach or book a fine dining experience in Tampa Bay, while the butterfly garden is another popular attraction.
Everglades City
A small town that lives and breathes nature—the talk of the town—and where the outdoors is a year-round celebration? No matter how you put it, Everglades City fits the caricature well, within the iconic wilderness but with a few surprises up its sleeve! While your mind scrounges up a vast, swampy wetland—picturesque nonenthels—upon mention, it is only a scratch in the bottomless barrel of the miles and miles of the diverse surrounding ecosystem, a wild “River of Grass." Offering a civilized sprinkle of culture, or a hearty dose of it, when you compare it to the very real alligator land and other critters, Everglades City is a must-visit!
Home to nature-loving residents who once moved here to get inspired every day, you can meet them at the cool local Island Cafe, not to mention the lodges, hotels, and clubs welcoming you to stay! Located at one end of the Wilderness Waterway, Everglades City is the gateway to the 10,000 Islands. Offering endless wet acres of marshes and mangrove forests, you can navigate along the open waters of the bay—one of the state's best places for canoeing or kayaking. With a variety of guided tours available, like airboats, through the old-growth forests, and swamp buggy rides, you can always take off on your own cycling excursion, a birdwatching trail, or enjoy relaxing fishing.
Islamorada
Abounding in family attractions, this must-visit town is home to the Theatre of the Sea with dolphin shows, the Alligator Reef Lighthouse, and shipwrecks at Indian Key Historic State Park, which you can explore in a kayak! Just 90 minutes south of Miami, the appropriately dubbed “Village of Island” spreads across six Florida Keys. Home to fabulous beaches, you can sunbathe, swim, and stroll, or take the gateway into Windley Key Fossil Reef Geological State Park. Islamorada is a dream to explore for adventurous couples, water sports enthusiasts, and fishermen, with its several annual fishing tournaments, sail fishing, and bone fishing.
The Florida Keys History and Discovery Center is a must-visit to get your hands on shipwrecks, Indigenous people, and pirates, which you can impersonate on a diving excursion for treasures and gorgeous sea creatures! It is also a favorite getaway to get your swag on with your little pirates! Whether you are a tropical drink kind of gal, a beer-loving lad, or love yourself some good ol' rum, the avid drinking culture here pulls you right in and mixes fabulously with the seafood scene! Florida Keys Brewing offers tours over tasting some of the limited releases and seasonal beers! With many ways to experience gorgeous sunsets, you can set sail on a private cruise into aqua blue, cross the Instagrammable bridges, at the water restaurant, or from the piers!
Mount Dora
Mount Dora, a charming town of about 16,000, feels idyllic, prepped with lakes and live oaks along the streets that offer an authentic and refreshing taste of Central Florida. Nestled on Lake Dora, you will find three freshwater lighthouses, while the well-kept town also features a century-old historic village. The downtown district, big on old-school charm, is both lively and quaint, thanks to the historic architecture and incredible restaurants throughout.
There is always a reason to visit Mount Dora's antique shops, eateries, and annual festivals, like the Mount Dora Arts Festival, a perennial favorite, on the first weekend of February with nearly 200,000 other out-of-towners! You can prowl through art galleries, modern furniture and decor for home, and local history museums here, where southern charm blends with lakeside vibes, with another, bigger Lake Eustis just northwest!
Rosemary Beach
This beachside cottage town with wide-open porches could not get any more charming but exciting, sure, with its incredible "French Quarter" feel downtown! Emanating real vacation feels, the Town Center is as much a shopping destination as a foodie paradise, with international restaurants and lively boardwalk promenades! You can meander the secret alleyways between the carriage houses, so foreign to city minds, with a feel of mysticism in the air that gets you daydreaming of faraway lands. But in all seriousness, Rosemary Beach, a Dutch village lookalike, is a close-knit community of good-ol American spirit who love lounging at the beach, socializing at local galleries, and dining al fresco.
The standout village with European vibes and beautiful architecture next to the ocean offers cottages and hotels with nearby remarkable landmarks along the Scenic Highway 30A. There is the must-visit Wesley House at Eden Gardens and Topsail State Park for kayaking tours, while South Walton Beach is a quick hop away. The aesthetic and young settlement, founded in 1995, makes you feel just as virile after a peaceful beach vacation and a stay at the stunning Pearl Hotel! You can unwind at the local pace among fellow shopaholics through the boutiques, the 30A Farmers Market, or at a delightful spa—and don't be surprised if you get an open-porch invitation!
Seaside
The town with the name emanating peaceful vibes is a little magnet with something to keep everyone a happy sailor! One of the best small beach towns in the Gulf of Mexico, Seaside is a sight to see, with pastel-colored houses lining the shore and beautifully decorated porches on a winding stroll along the backstreets! A real 20th century beauty, it boasts a new urbanist architectural design with a ton of beach access spots and beautiful outdoor spaces like Cerulean Park right next to the WaterColor Trail System and a stroll to Viridian Park!
The sugar white sand beach, never overcrowded, is a stone's throw away from the pedestrian-friendly streets downtown—a star in The Truman Show! The town in northwest Florida, named the prettiest by Architectural Digest, is pure joy to wander around quaint cafes, like the most popular Great Southern Cafe, food vendors in airstreams, and bikable lanes to explore outward! Seaside imprints in your memory as a quaint New England town or an exotic European destination, white picket fences included! Stark against the waters, the resort town offers many b&bs and rentable places to call home, thanks to its many part-time residents.
Stuart
Stuart, a must-visit town along Florida’s Atlantic Coast, is the “Sailfish Capital of the World,” which speaks volumes to maritime fans. With opportunities for water sports, fishing, and boat tours along Florida’s Treasure Coast, Stuart also appeals to families seeking timeless small-town charm. Perfect for a weekend escape, you can spend a Saturday morning at the Stuart Green Market, a live event every Sunday morning at City Hall, and make a stop for heritage at the Road to Victory Military Museum and another one at the Stuart Heritage Museum.
With family pursuits for every taste along the boardwalk following the St. Lucie River, notable hotspots include an antique car collection at the Elliott Museum. Just a hop to the historical downtown with dining and shopping, you can return for a romantic sunset stroll. Check out or check into the colorful Old Colorado Inn, while the House of Refuge at Gilbert’s Bar is an old haven for shipwrecked sailors in the 1900s. From trails, state parks, and preserves to the Indian River Lagoon, there are also butterfly gardens and sea turtle nesting areas, so the town is sure to please the active and put the little wanderers in awe!
In wrapping up our tour of Florida's small-town treasures, we're reminded that true vacation magic is found in the unexpected—a quiet fishing pier at dawn, a hidden cafe serving the freshest catch, or a cozy inn nestled among pastel cottages. Everglades City, Cedar Key, Rosemary Beach and others offer not just a retreat from the hustle of daily life but an invitation to a different rhythm altogether.
