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 upscale and beautiful coastal community where fishing is a way of life and shelling is a favorite hobby. Having won over the likes of Katharine Hepburn, this charming village off the Gulf Coast attracts a steady stream of vacationers and sunshine-seekers eager to follow in her footsteps. Every activity feels like a delightful indulgence. After pedaling the six-mile Boca Grande Rail Trail along the length of the island, be sure to collect your sea treasures at the beachfront Gasparilla Island State Park. The gentle turquoise surf at your feet is perfect for fishing or snorkeling before you watch the sunset behind Gasparilla Island Lighthouse.
Adorable decorations decorate the Port Boca Grande Lighthouse and Museum during the winter holidays, which are open for tours. Don't miss the iconic Keylime Bistro inside the historic downtown train station for a sophisticated meal with a casual feel or a dessert. Surrounded by inviting islands just a short boat ride away, nearby Cayo Costa offers access by kayaking or motorized boats to a nine-mile stretch of sandy, undeveloped shoreline perfect for swimming, fishing, and shelling with hardly anyone around. Retaining its Old-Florida charm through renovations and updates, the circa-1911 Gasparilla Inn & Club radiates 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 explore a variety of species, while Turner Beach provides a spot for swimming and saltwater fishing from the shore or rock jetty. Pedal around and stop at The Mucky Duck Neighborhood Pub and the colorful RC Otter’s Island Eats. Whether you're here to hit the beach or enjoy peaceful 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 stunning gulf views. For a full wildlife island experience, book a dolphin spotting tour and enjoy birdwatching amid the vibrant tropical landscape of giant cacti and bougainvillea vines as a picturesque backdrop.
DeLand
Situated between Orlando and Daytona Beach, DeLand offers numerous outdoor recreation options popular with families and friends on a getaway. It’s also a favored stop for coast-bound motorcyclists who appreciate its cultural charm. Just about 30 minutes from the Atlantic Ocean, DeLand makes an ideal base to explore Old Florida's charm alongside beach outings, blending a youthful college atmosphere with rich cultural experiences. After breakfast at Cook's Buffet Cafe Bakery, visitors can enjoy vibrant art displays, such as the original DeLand Wings mural along the Wings of the West Mural Trail in Downtown DeLand. The charming downtown area features 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, architecture enthusiasts should visit the Stetson Mansion. The Homer and Dolly Hand Art Center at Stetson University is open year-round, or visit during the spring when the multi-day DeLand Outdoor Art Festival attracts thousands of visitors and over 100 artists and crafters. Surrounded by wildlife refuges, preserves, and scenic drives, the Reptile Discovery Center features alligators, venomous and nonvenomous snakes, and tortoises year-round. For a winter escape, enjoy the manatees at Blue Spring State Park in Orange City, just next door, where visitors can stroll the boardwalk. The area also offers paddling on the St. Johns River and swimming in warm freshwater springs during the summer.
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 its compact downtown, alongside independent shops for gifts and home decor. Come see the spring training home of the Toronto Blue Jays or attend one of the events celebrating 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 mild, breezy winter weather is ideal for enjoying the beachside ambiance and historic sites, exploring the St. Marys River waterways, or venturing onto the Atlantic Ocean for a snow escape. Walk along the pedestrian-friendly streets featuring Victorian-style buildings, and visit Fernandina's Fantastic Fudge, a longstanding local favorite, nestled among popular restaurants and shops. Fort Clinch State Park showcases a historic fort from around 1864, offering guided tours, wildlife observation, camping, and nature trails. During the May Isle of Eight Flags Shrimp Festival, consider staying at a luxurious resort or a charming B&B to relax after watching the sunset behind the historic Amelia Island Lighthouse, built in 1838 and open for 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 offers a relaxing escape to browse a unique collection of independent shops and boutiques, ideal for beginning your holiday shopping among local artists, bookstores, and home décor stores, along with antiquing spots and indulgent spas. After visiting the Gulfport History Museum for local history, you're just a block south to the waterfront. Switch between the beach, picnic areas, and sand sports at Gulfport Beach Recreation Area, with nearby shops and restaurants. As a top dining spot for every budget—from sandwiches and burgers to fine dining—O'Maddy's Bar & Grille is a casual gathering place for drinks and American bites with outdoor seating. Enjoy live entertainment around town and watch the sunset next door 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.
Travel experts from New York Travel Guides highlight Marathon as one of the most romantic small towns in the US, ideal for sparking romance. Visitors can participate in activities such as boarding, windsurfing, and paddlesports at The Lagoon on Grassy Key or explore local seafood markets. When craving a meal, they can choose from Cuban-inspired restaurants and watch the sunset at Faro Blanco Marina, located just north, behind a lighthouse and palm trees. Near the community park, there's a surf 'n' turf venue with a stone grill, serving lobster tails and featuring a nautical theme close to another marina. For those seeking adventure or relaxation, many couples enjoy sunset cruises with Marathon Mermaid Charters. The historic Old Seven-Mile Bridge offers access to the western keys along US Route 1/Overseas Highway.
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.
Covering just four square miles, Palm Beach exudes sophistication and the aura of "Old Money' set against a lush tropical backdrop of tall palms. Visitors can enjoy a walk past grand mansions and luxury resorts or cycle along the Lake Trail, a five-mile route that follows the Intracoastal Waterway dotted with yachts and exquisite homes. The Breakers, a luxurious oceanfront resort in Italian Renaissance style, dates back to the 1800s. The area boasts numerous attractions, including three beachfront parks. Phipps Ocean Park offers a grassy picnic area shaded by mature trees and oceanfront Tiki huts, while R.G. Kreusler Park features a boardwalk leading to the beach, where shells and sea glass can be found. From Atlantic beaches to an oceanfront golf course, watch the sunset behind towering 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 small but beloved town. A true hidden gem with a peaceful beach and European vibes along Main Street, check out or stay at the stunning Pearl Hotel. Perfect for romantic getaways, it attracts honeymooners, sightseers, and architecture enthusiasts, all drawn to its beautiful buildings featuring iconic modern designs that evoke a Greek holiday. With an upscale yet relaxed atmosphere, the cobblestone streets are lined with award-winning restaurants, boutiques, shops, and parks. Pescado Seafood Grill & Rooftop Bar offers unbeatable views, while the thoughtfully curated Hidden Lantern Bookstore invites you in with a cozy 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 following morning, visit the small shopping center to find breakfast options such as Jerry's Foods, where you can enjoy your morning coffee and pick up groceries for a picnic. Afterward, drop off shopping bags filled with island boutique items and gifts at your hotel. The Blue Giraffe Food Truck, open Monday to Saturday at Periwinkle Place Shopping Center, offers a quick meal. Sanibel’s lack of stoplights and tall buildings, with only palm trees reaching high, adds to its inviting atmosphere. With over 25 miles of shared-use paths, you can rent a bike from Billy’s Bike Shop and explore Wildlife Drive at J.N. “Ding” Darling National Wildlife Refuge, a 6,400-acre protected area home to reptiles, amphibians, mammals, and more than 245 bird species within 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 discover Venice’s rich history or bike through this Silver Bicycle Friendly Community, also known as Monarch City USA. Then, you can wander along a charming collection of boutiques, restaurants, and bars, browsing sweet treats and services. The family-owned businesses showcase local hospitality, including Hotel Venice, San Marco Hotel, and the Orange Blossom Garage. All of this makes Venice an inviting escape, perfect for some "me time" or a friends' getaway. Shop and dine to your heart’s content while immersing yourself in the culture of the Shark Tooth Capital of the World, where you can bring home real shark teeth as souvenirs from the beach, along with 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.
