12 Of The Most Captivating Small Towns In Florida
America’s southernmost state is one of the most visited and prettiest. From Dunedin's unspoiled, sand-fringed islands to Marathon's 13-island coverage, each capturing Florida from various sides. The Sunshine State is more than the famous Orlando rides and the glitzy charm of Miami. Offering natural scenery from white sand beaches to tropical forests and virtually endless wetlands, Sanibel's National Wildlife Refuge houses the largest undeveloped mangrove ecosystem in the US.
With a beachy vibe for each taste, including friends looking to party or family-friendly fun, enjoy pristine beaches of the lesser-known towns like Gulfport, a funky, artsy town in a scenic enclave of artists and creatives. Whether you're hunting for seashells in Sanibel or the cultural landmarks in Fernandina Beach, having flown eight flags on the captivating Amelia Island, these small towns embody the type of atmosphere that you never want to leave.
Boca Grande
Just northwest of Fort Myers on Gasparilla Island, Boca Grande is an affluent and beautiful coastal community where fishing is a way of life and shelling is a hobby. Having captivated the likes of Katharine Hepburn, this idyllic village off the Gulf Coast attracts a relentless string of vacationers and sunshine-seekers to explore in her footsteps. Every activity feels like an indulging treat. After pedaling the six-mile Boca Grande Rail Trail stretch along the length of the island, don't forget to collect your sea treasures at the beachfront Gasparilla Island State Park. The lapping turquoise surf at your feet is perfect for fishing or snorkeling before capturing the sunset views behind Gasparilla Island Lighthouse.
Adorable decorations adorn the Port Boca Grande Lighthouse and Museum during the winter holidays, open for tours. Don't miss the iconic Keylime Bistro within the historic downtown train station for a sophisticated meal in a casual feel or a dessert. Surrounded by beckoning islands just a short boat ride away, the nearby Cayo Costa offers access via kayaking or motorized boats to experience a nine-mile string of sandy, undeveloped shoreline for more swimming, fishing, and shelling with virtually no soul in sight. Having retained its Old-Florida charm through renovations and updates, the circa-1911 Gasparilla Inn & Club exudes a sense of affordable luxury, at least for one spa treatment.
Captiva
Captiva is a town, or rather an island, that does a great job introducing itself as a person of few words, but the scenery—is worth a million. Just an hour from Fort Myers on Florida’s Southwest Coast, the island entices artists and photographers to capture the scenery and stunning sunsets that draw visitors from far and wide. Popular among couples on a secluded getaway, Captiva Island is just as perfect for families seeking a change of pace. Just north of its sister island, Sanibel, it's easy to make a whole vacation out of exploring the area, including golf, scuba diving, snorkeling, and shelling. The long stretches of captivating white-sand beaches transport you into a paradise with turquoise waters, set for thrilling water sports.
Join the sailors or book a fishing charter to venture for a wide range of species, while Turner Beach offers up its own stretch for swimming and saltwater fishing from the shore or rock jetty. Pedaling around, stop at The Mucky Duck Neighborhood Pub and the colorful RC Otter’s Island Eats. Whether you're here to hit the beach, enjoy serene kayaking and paddleboarding adventures through Roosevelt Channel and around Buck Key Preserve, Tween Waters Island Resort & Spa and South Seas Island Resort offer private beaches and beautiful gulf views. For a complete wildlife island experience, book a dolphin spotting tour and enjoy birding amid the colorful tropical topography of giant cacti and bougainvillea vines as a picturesque backdrop.
DeLand
Hidden between Orlando and Daytona Beach, DeLand is replete with opportunities for outdoor recreation as popular among families and friends on a getaway. It is a favorite pit stop among coast-bound motorcyclists alike with a soft spot for culture. Some 30 minutes from the Atlantic, make DeLand your perfect base to sift through Old Florida charm in between the due beach time, with a youthful college vibe and captivating cultural opportunities. Sauntering from breakfast at Cook's Buffet Cafe Bakery, you will encounter vibrant art displays, like the original DeLand Wings mural in Downtown DeLand along the Wings of the West Mural Trail. The quaint downtown bursts with museums, including the Museum of Art, Veterans Museum, and DeLand Naval Air Station Museum.
From the DeLand Sculpture Walk and DeLand Historic Mural Walk to the DeLand Black Heritage Trail, the architecture fans shouldn't miss the Stetson Mansion. Stop by the Homer and Dolly Hand Art Center at Stetson University anytime, or next spring, when thousands of visitors and over 100 artists and crafters will gather for the multi-day DeLand Outdoor Art Festival. Surrounded by wildlife refuges, preserves, and scenic drives, the year-round Reptile Discovery Center hosts alligators, venomous and nonvenomous snakes, and tortoises. Escape the snow home for a sojourn with delightful manatees who enjoy wintering at Blue Spring State Park, with a boardwalk, next door in Orange City. It's great for paddling the St. Johns River, plus freshwater springs to swim in the warm months.
Dunedin
This Gulf Coast town boasts a charming downtown and sand-fringed islands with unspoiled wildlife, like the seasonal Caladesi Island Park. Summoning nature lovers from all over to explore the state's captivating fauna and flora, being a designated trail town, you can pedal from the bike-friendly downtown to the Pinellas Bike Trail on the mainland to Causeway Community Park. Hop on and off Caladesi's Mangrove Shell Tree trail to the miles of unspoiled white sand beaches for combing in serenity to the sound of the beating waves. Dunedin is a captivating town with a family-friendly feel, art galleries, like the Fine Art Center, and a city pier, popular for fishing, strolls, and local sights to get captivated in your own way.
Explore the oceanscape on a fishing charter, paddleboard, or kayak, and hit the trails on foot or bike, like the popular Osprey Trailhead on Honeymoon Island, known for swimming, fishing, and hiking along the shell-strewn shores. Just 30 minutes west of Tampa, along the 45-mile paved Fred Marquis Pinellas Trail, which runs from Tarpon Springs to Tampa, Dunedin is one of the oldest towns on Florida's west coast. Founded by two Scotsmen in 1899, it is a popular stop today for craft beer and outdoor dining through compact downtown, alongside independent shops for gifts and home decor. Come see the spring training home of the Toronto Blue Jays or one of the events that honor Dunedin’s Scottish history, and catch the sunset from the pier.
Fernandina Beach
Home to attractive beaches and shiny attractions on Florida's northeastern coast, this Amelia Island enclave boasts a captivating cultural heritage, having once flown different flags under eight nations, starting deep in 1562 with the French. From Spanish to English, Patriot and Green Cross, when led by a Scottish-born soldier of fortune, it belonged to the Mexican Rebels before becoming confederate and raising its US flag. Visitors enjoy a hunt for clues through landmarks, year-round golf, and beachcombing the 13 pristine miles in picture-perfect views, like the vastly scenic sandy seashore of Peters Point Beachfront Park. Amelia Island Museum of History is an old jail focusing on local history starting from the Timucuan Indian.
The warm, breezy, mild winter is perfect to revel in beachside charm and historic appeal, take on the St. Marys River waterways, or explore the open Atlantic waters on a getaway from the snow back home. Strolling the walkable streets along the Victorian architecture downtown, stop by the decades-old Fernandina's Fantastic Fudge among popular restaurants and shops. Fort Clinch State Park flaunts a circa-1864 fort with guided tours, wildlife viewing, camping, and nature trails. When you visit during the May's Isle of Eight Flags Shrimp Festival, choose a pampering upscale resort or an adorable B&B to turn in after the sunset views behind the historic Amelia Island Lighthouse, constructed in 1838 with monthly tours.
Gulfport
This scenic enclave across St. Pete Beach is a convenient getaway from the city with captivating attractions. While the name relays its Gulf Coast location, the funky, artsy town is more than a historic port; it is an active community of artists and creatives. It all comes together at the heart of the historic downtown area—the Beach and Shore Boulevards are situated right on scenic Boca Ciega Bay. Just inland, Tomlinson Park features a playground and exercise equipment, plus a little lake and fountain. Birds frequent the park, and it's just very quiet to relax in local nature. Offering attention-grabbing accommodations, like the Jamaica and Aruba-themed rooms at the Sea Breeze Manor, inspire a Marrakech or Serengeti stay at the Peninsula Inn or rent from independent owners.
Gulfport can be a relaxing escape to browse a unique lineup of independent shops and boutiques, perfect to start your holiday shopping among local artists, bookstores, and home décor, among antiquing spots and indulging spas. After a stop at the Gulfport History Museum for local history, it is just a block south to the waterfront. Hop between the beach, picnic tables, and sand sports along Gulfport Beach Recreation Area, with nearby shops and dining. As a premier dining destination to fit all price ranges, from sandwiches and burgers to fine dining, O'Maddy's Bar & Grille is a laid-back hub for drinks and varied American bites with an outdoor space. Enjoy live entertainment on the side throughout town and catch the sunset next door east at the marina.
Marathon
This captivating destination to explore in the middle of the Florida Keys is an hour’s drive from Key West. The 10-mile-long, family-friendly community of 13 islands boasts rich maritime history, 1,200 wet slips, and 1,200 dry slips—a boating and sailing paradise. Drawing visitors from all over, its calm, turquoise waters lap up Sombrero Beach just south of downtown, perfect for a swim, picnics, and sand volleyball, plus loggerheads nesting from April to October. The Turtle Hospital offers guided tours and feedings, plus a gift shop, while Florida Keys Aquarium Encounters offers touch tanks and a cafe. From snorkeling and scuba diving among coral reefs to fishing and paddling, the landbound enjoy camping and hiking at the 1,000-acre Curry Hammock State Park.
Having made the list of the most romantic small towns in the US, travel experts at New York Travel Guides agree that Marathon has what it takes to let the sparks fly. Learn boarding, windsurfing, and paddlesports at The Lagoon on Grassy Key or browse for seafood at local markets. When hunger strikes, choose among Cuban-inspired restaurants and catch the sunset just north at Faro Blanco Marina, behind a lighthouse and palms. Next to the community park, there's a surf'n'turf with a stone grill, lobster tails, and a nautical theme near another marina. Whether you're an adventurous couple or looking to relax, many enjoy Marathon Mermaid Charters for a sunset cruise. The historic Old Seven-Mile Bridge offers access to the western keys along US Route 1/Overseas Hwy.
Palm Beach
Having captivated the Kennedys as their official vacation spot, make Palm Beach your tropical playground in any season. Its golden sands have been commonly scribbled into day planners among movie stars and tycoons during the Gilded Age, making it rightfully “America’s First Resort Destination.” Just across the bridge from West Palm Beach, this sliver of a barrier island welcomes families, beach lovers, and music fans alike. Near the Town of Palm Beach Municipal Beach, Worth Avenue, apt in its name, is a high-end shopping district, with Chanel and Jimmy Choo through boutiques, plus Whitehall, a Gilded Age mansion, open to the public. Lilly Pulitzer boutique offers bright, signature prints, while Royal Poinciana Plaza flaunts upscale shops in a lush setting.
Just four square miles of land, Palm Beach oozes elegance and "Old Money" against the tropical backdrop of towering palm trees. Take a stroll along mansions and resorts or pedal the Lake Trail, a five-mile path winding the Intracoastal Waterway with its yachts and mansions. The Breakers is an elegant, Italian Renaissance-style oceanfront resort dating to the 1800s. There's a wealth of attractions to soak up the charm, like three beachfront parks. Phipps Ocean Park features a grassy picnic area under mature trees, plus oceanfront Tiki huts, while R.G. Kreusler Park offers a boardwalk to the beach for a swim, with seashells and sea glass strewn along. From Atlantic beaches to an oceanfront golf course, catch the sunset behind massive yachts at Palm Beach Marina.
Rosemary Beach
Located off the famous Scenic Highway 30A, on the Northwest Coast of Florida, east of Destin, Rosemary Beach is a tiny but well-loved town. A real hidden gem with a peaceful beach and European vibes on Main Street, check out or into the stunning Pearl Hotel. Perfect for romantic holidaymaking, it is popular among honeymooners, sightseers, and architecture fans alike, among other beautiful buildings of iconic modern designs that inspire a Greek holiday. Boasting an upscale feel with a relaxed atmosphere, the cobblestone streets are lined by award-winning restaurants, boutiques, shops, and parks. Pescado Seafood Grill & Rooftop Bar serves over unbeatable views, while the thoughtfully curated Hidden Lantern Bookstore captivates you in a corner with a read.
Community and Summer Kitchen Café is bright and beachy to start the day after on a high, or enjoy a fun company over beer, wine, and desserts. Stop by the 30A Farmers' Market for fresh-prepared meals, groceries, produce, and a wine selection, feeling one with the locals. La Crema Tapas and Chocolate is Madrid/Barcelona-inspired with its menu of traditional tapas and small plates. From beach cottages to luxurious hotel stays, the Rosemary Beach Inn is a European-style boutique hotel right in the heart of town. Just a stroll to the beach fringe, explore the sands further east with sun-kissed real estate envy on the other side to your perfect spot, which you can elevate with a stop at Light Me Up Beach Bonfires, a beach entertainment shop.
Sanibel
At 12 miles long and three miles across, the prevailing sense of peace becomes apparent even before you reach the shore of this pristine island paradise. The warm climate and intimate feel envelop you in a dreamlike surroundings, where you will find yourself in a crouch position, so-called “Sanibel Stoop,” along the beach among globe-trotting visitors. Thanks to its unique east-west orientation, the turquoise surf washes 400 types of seashells ashore every day to sift through thousands of pastel-colored treasures, display them as a memory of the “Seashell Capital of the World," and gift one to a friend. From Bowman's Beach to Blind Pass, there's plenty of room to roam, spread out in serenity, and enjoy photoshoots. For dinner, you can look forward to Cielo, Doc Ford’s Rum Bar & Grille.
The next morning, explore the small shopping center in search of breakfast, like Jerry's Foods for your morning java and groceries for a picnic after dropping off the shopping bags at your hotel filled with goodies from the island's boutiques and gift shops. Open Monday through Saturday, Blue Giraffe Food Truck is great for a quick bite at the Periwinkle Place Shopping Center. With no stoplights and no buildings taller than the tallest palm, Sanibel's warmth and charm will captivate you. Boasting 25+ miles of shared-use paths, rent a bike at Billy’s Bike Shop and explore Wildlife Drive at J.N. “Ding” Darling National Wildlife Refuge, a 6,400-acre preserve housing reptiles, amphibians, mammals, and over 245 species of birds in the largest undeveloped mangrove ecosystem in the US.
St. Augustine
Founded by Don Pedro Menendez de Aviles of Spain in September 1565 along the northeast coast of Florida on the Matanzas River, St. Augustine is the longest continually inhabited European settlement in the US. You can stroll right up to the Atlantic in the morning and catch a show at the Oldest Wooden Schoolhouse after sunset, filling time in between along the historic streets. From carriage rides to wholesome 21st-century family fun, it never fails to spellbind visitors of all ages and interests. Set off in a kayak or golf with the pros, and fine dine on the fresh catch of the day after some shopping through colonial architecture for chic finds. The historic black-and-white striped St. Augustine Lighthouse & Maritime Museum, built in 1874, offers tours, a museum, and a shipyard playground.
The "Nation’s Oldest City" has tales to tell along the narrow lanes, through museums, plus four centuries worth of influences. Experience Spanish, English, Greek, Native American, and African American in landmarks and cuisine before sprawling out along the beautiful Anastasia Beach. Nearby, Castillo de San Marcos National Monument Historic Fort offers self-guided tours of the drawbridge and the gun deck against captivating Matanzas Bay views. Plan your trip to St. Augustine with a stop at Ponce de Leon's Fountain of Youth Archaeological Park, showcasing 16th-century Spanish settlement with sites and cannons. The 1965 St. Augustine Amphitheatre is perfect for a stroll along the arboretum before an outdoor showcase of live entertainment to end the perfect day.
Venice
Blending history and 21st-century attractions, Venice is a captivating city on the Gulf Coast, upholding historic charm, tourist popularity, and its own economic virility. From the old Venice Train Depot to the antiquated 1920s buildings, the historic district displays charms of the yesteryear through architecture, cultural establishments, and businesses on Tampa Avenue, home to sites that shaped its development. Centennial Park at the heart offers free parking to catch a free concert at the gazebo and let the kids monkey around the Intergenerational Fountain splash pad. Having captured Bloom's "Outstanding Achievement Award," the Venetian Waterway Park and The Legacy Trail, for instance, connect miles of walking and biking paths back to the "Coolest Downtown."
Take a walking tour to learn about Venice’s fascinating history or bike through this Silver Bicycle Friendly Community, also known as Monarch City USA. Then you can wander along the heartwarming assortment of boutiques, restaurants, and bars, sifting through sweet treats and services. The family-owned businesses display local hospitality, including Hotel Venice, San Marco Hotel, and the Orange Blossom Garage. All this makes Venice an enticing escape, perfect for some "me time" or a friends getaway. Shop and dine your heart out while absorbing the culture of the Shark Tooth Capital of the World, where you can bring home real shark teeth as souvenirs from the beach, plus organic produce, baked goods, and seafood at the Venice Farmers Market on Saturday mornings.
Vacation Kennedy-style amid Gilded Mansions like Whitehall and high-end shopping boutiques, along the sliver of a barrier island called Palm Beach, aka “America’s First Resort Destination." Captiva Island is all in its name, next to its sister Sanibel, "the Seashell Capital of the World." Rosemary Beach inspires a Greek holiday with its beautiful buildings of iconic modern designs, while Boca Grande stole Katharine Hepburn's heart.
These towns and small cities captivate visitors with warm hearts through cultural attractions that will make you want to extend your getaway just another day longer. From off-the-beaten-path to convenient escapes, get away amid the stunning natural beauty of Florida's Historic Coast in the US's oldest settlement, St. Augustine. Each makes for a memorable road trip stop or an unforgettable holiday destination under the infamous sunshine.
