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11 Small Towns in Florida With Big Charm

by Staff

Beyond its famous theme parks, pristine beaches, and buzzing nightlife, Florida is home to charming small towns showcasing a quaint, less-explored side of the Sunshine State. While most travelers flock to its glitzy metropolises like Miami and Orlando, the smaller, quieter communities possess a unique appeal that often leaves first-time visitors enchanted and eager for more. Shielded from urban chaos and rowdy crowds, these towns offer a breath of fresh air for Florida vacationers.

Numerous destinations around the state await exploration, from historic waterfront villages to picturesque inland getaways. These hidden gems boast pristine natural scenery and friendly locals with a strong sense of community. They also offer a unique culture, captivating history, and exciting outdoor opportunities to keep visitors entertained. Whether you’re looking to discover historical landmarks, sample novel culinary offerings, or experience gorgeous beach scenery, here are some charming towns in Florida you should visit.

Anna Maria Island

Aerial view of Anna Maria Island

Sandwiched between the mainland of Florida’s peninsula and the scenic Gulf of Mexico, this tiny resort town excites with spectacular coastal scenery. It boasts expansive beaches with white, sandy shores, notably Manatee Public Beach. This seaside paradise draws beachgoers thanks to a family-friendly atmosphere and amenities like restrooms, bike racks, picnic tables, and a playground.

You can soak in the stunning scenery along the historic Anna Maria City Pier. The picturesque platform has hosted sightseers since 1911 and serves as a stark reminder of the city’s early years. Several businesses, from shops and bars to restaurants, line the pier. Stop by City Pier Grill and Bait to enjoy fresh seafood and cocktails while enjoying live music. Lastly, a popular activity on the island is exploring its waters, with options like the Anna Maria Island Dolphin Tours offering a chance to spot local marine life.

Fernandina Beach

Main street of Historic town center of Fernandina Beach on Amelia Island
Main street of Historic town center of Fernandina Beach on Amelia Island, via peeterv / iStock.com

This quaint coastal getaway on Amelia Island spoils vacationers with 13 miles of white, sandy beaches. It offers a harmonious blend of coastal charm and inland attractions with a walkable downtown housing an array of charming businesses. For the outdoorsy traveler, one of the highlights is Fort Clinch State Park. Stretching over 1,100 acres, it provides ample opportunities for hiking, fishing, wildlife viewing, and shark tooth collecting, and houses the historic Fort Clinch. Those interested in the town’s history can visit the Amelia Island Museum to browse a collection of exhibits inside the Old Nassau County jail, listed on the National Register of Historic Places. While exploring the pedestrian-friendly downtown, a stop at the Island Art Association Gallery is an excellent opportunity to immerse in the local art scene. The establishment displays unique pieces by various artists and offers classes for those interested.

Apalachicola

Street view of the Dixie Theater in Apalachicola, Florida
Street view of the Dixie Theater in Apalachicola, Florida

Apalachicola is a charming town located along the Gulf of Mexico, on the shores of the picturesque Apalachicola Bay. Its modest population of about 2,300 residents offers a quiet getaway in rural Florida. The town boasts a mix of historical sites, starting with the John Gorrie Museum State Park. Nestled within the historic district, this simple establishment displays unique artifacts, photographs, footage, and other relics honoring John Gorrie, the inventor credited with creating the concept of air conditioning. Another must-see site is the Raney House Museum, an 1800s residence that belonged to a local cotton trader, now housing several historical artifacts.

If you want to step outside, it doesn’t get better than the scenes along the Scipio Creek Boardwalk. The relaxed route stretches about a quarter of a mile, leading to a scenic lookout offering sweeping views of the Apalachicola River. Lastly, do not forget to stop by Oyster City Brewing Company Apalachicola to relax with refreshing craft beer in an easygoing atmosphere.

Winter Park

Downtown Winter Park, Florida.
Downtown Winter Park, Florida.

A sweet escape from the crowded streets of Orlando, Winter Park has a small-town vibe, a thriving arts community, and relaxed outdoor spaces. Noteworthy points of interest include the Charles Hosmer Morse Museum of Natural Art, which boasts the most comprehensive art collection by Louis Comfort Tiffany. Historians will appreciate a tour of the Casa Feliz Historic Home Museum, showcasing classic Andalusian-style architecture in this beautifully preserved farmhouse designed by architect James Gamble Rogers.

You cannot ignore the beautiful outdoors in Winter Park, and Kraft Azalea Garden presents the perfect nature space to relax and unwind. The small, peaceful park is dotted with azalea and cypress trees, offering ample shade from the scorching sun. Central Park, another cozy space, sits in the heart of the busy shopping district, offering a tranquil retreat.

Matlacha

Street view in Matlacha, Florida
Street view in Matlacha, Florida, via Felix Mizioznikov / Shutterstock.com

Matlacha, located on Pine Island, is easily one of Florida’s most picturesque small towns and a sought-after holiday destination. Its charm is evident in the multiple natural spaces around the town, providing an ideal setting for leisurely activities. A prime example is Matlacha Community Park, featuring a lovely pier with sweeping water views, alongside a playground and basketball courts. Combine your love for the arts and the outdoors at the Leoma Lovegrove Gallery & Gardens, where you can appreciate colorful pieces by painter Leoma Lovegrove, set amidst beautifully manicured gardens.

If traveling with family, take the young ones to Cw Fudge Factory, which offers a range of homemade delicacies, including fudges, candies, popcorn, and ice cream. For a more substantial meal, visit Blue Dog Bar & Grill to enjoy some tasty seafood, complemented by a glass of wine.

Naples

Tourists walking and shopping along the restaurants and luxury stores of 5th Avenue in downtown Naples, Florida
Tourists walking and shopping along the restaurants and luxury stores of 5th Avenue in downtown Naples, Florida, AevanStock / Shutterstock.com

Despite being one of the smaller towns in Florida, Naples offers a remarkable array of tourist attractions. From world-class shopping opportunities and high-end waterfront resorts to a recognized local arts scene, Naples caters to a wide range of interests. The Naples Botanical Gardens embody the natural beauty surrounding this Gulf of Mexico town. This enchanting 170-acre oasis hosts a diverse range of tropical plants, one of the richest collections in the region. Meanwhile, the historic Naples Pier is a favorite for both tourists and locals, offering panoramic views of the Gulf of Mexico and opportunities for bird-watching, sunset viewing, and dolphin-spotting.

For those with a penchant for shopping, Naples boasts an impressive downtown with a premier commercial district, home to a mix of renowned shopping stores and dining options. Consider visiting Tin City Waterfront Shops for an unforgettable retail therapy experience. Lastly, don’t forget to show some TLC to the fantastic animals at Naples Zoo at Caribbean Gardens.

Islamorada

Visitors feeding fishes and pelicans in Islamorada, Florida.
Visitors feeding fishes and pelicans in Islamorada, Florida.

Known as the ‘Village of Islands,’ Islamorada encompasses six of the Florida Keys and delights with remarkable water adventures, offering spectacular beach scenery and colorful coral reefs. Explore the area’s rich diving culture at the History of Diving Museum, which exhibits a vintage collection of diving equipment and artifacts, celebrating the area’s underwater diving heritage. At Theater of the Sea, enjoy entertaining live performances, including sea lion, parrot, and dolphin shows, for some family-friendly fun.

For a more secluded experience, the Indian Key State Historic Site offers a tranquil environment. This 11-acre island was once home to a thriving diving community in the 1800s but is now deserted, with only the town ruins remaining.

Stuart

Old Stuart Department Store building, now Stuart City Hall Annex, NW corner of SW Flagler Avenue and SW St, Lucie Avenue, Stuart, Florida
Old Stuart Department Store building, now Stuart City Hall Annex, NW corner of SW Flagler Avenue and SW St, Lucie Avenue, Stuart, Florida, By Stephen B Calvert Clariosophic – Own work, CC BY-SA 3.0, Wikimedia Commons

Stuart, a prime summer destination on Florida’s Atlantic Coast, is renowned for its sport fishing heritage and a pedestrian-friendly downtown. Strolling through its quiet streets, you’ll discover gems such as the Stuart Heritage Museum, where you can explore the town’s history, dating back to its pioneer days, through a collection of artifacts and relics. Visit Stuart Boathouse to sample sumptuous seafood and steak in an upscale atmosphere, complemented by soothing live music.

Outdoor enthusiasts can find a cozy spot at Shepard Park, a waterfront green space featuring secluded picnic areas with grills for quality time with family, and a scenic boardwalk along the river, ideal for fishing. Halpatiokee Regional Park, spanning 65 acres, offers diverse outdoor activities, from biking and hiking to kayaking.

Crystal River

Tourists from around the world travel to Three Sisters Springs in Crystal River, Florida.
Tourists from around the world travel to Three Sisters Springs in Crystal River, Florida. Editorial credit: Nicole Glass Photography / Shutterstock.com

Crystal River is a nature lover’s paradise, providing enthusiasts with the rare opportunity to swim with Florida’s most famous marine resident, manatees. This relaxed coastal retreat on the western side of the state delights with a mix of exciting natural pursuits showcasing the beauty of rural Florida. The town is nourished by gentle springs, and at Three Sisters Springs, visitors can admire manatees swimming in the crystal-clear waters. The site is part of the Crystal River National Wildlife Refuge, an 80-acre sanctuary established to preserve the West Indian manatee and diverse state habitats.

If you want to venture into the emerald-green waters of the Gulf of Mexico, several local outfitters offer exciting excursions. Fun 2 Dive Manatee Tours allows guests to swim and snorkel with these gentle giants in the warm waters of Crystal River. For some background on this beautiful town, visit the Coastal Heritage Museum, housed in the Old City Hall, to browse documents and artifacts highlighting its rich past.

Captiva

Beach houses in Captiva, Florida
Beach houses in Captiva, Florida

Captiva, with its crystal-clear beaches, pristine tropical topography, and spectacular sunsets, epitomizes a seaside nirvana in Lee County, Florida. Beachgoers can look forward to endless fun on its white sandy shores, with options like Turner Beach offering a family-friendly setting ideal for activities like shell collecting, fishing, picnicking, sunbathing, and sunset watching. Adventure Sea Kayak & SUP plans fun water activities for tourists, ranging from kayaking and standup paddle-boarding to wildlife tours. Captiva houses a string of beachside eateries serving the best seafood in an easygoing atmosphere. The Mucky Duck Restaurant, an excellent choice for local delicacies, offers great cocktails to enjoy while soaking in stunning sea views. For art lovers, Jungle Drums Gallery is a must-visit to admire both indoor and outdoor exhibits of coastal and wildlife art.

St. Augustine

Waterfront view in St. Augustine, Florida
Waterfront view in St. Augustine, Florida

St. Augustine’s claim to fame lies in being the oldest city in the United States, with a legacy dating back to 1565. The city houses a treasure trove of historical gems, notable for their unique Spanish colonial architecture. As you walk along the town’s calm, cobblestone streets, you will encounter sites like Castillo de San Marcos National Monument, the oldest stone fortress in continental America. Another noteworthy landmark is the Lightner Museum, which impresses with its Spanish Revival Renaissance façade, housed in the iconic Hotel Alcazar building.

Also, be sure to visit the Old Jail Museum, listed on the National Register of Historic Places. Constructed in 1891, it served as the St. Johns County Jail. But St. Augustine isn’t just about history; for a different experience, consider visiting the St. Augustine Alligator Farm Zoological Park to view over 20 species of crocodiles and a range of other reptiles, birds, and mammals.

Final Thought

From breathtaking beach scenery and picturesque tropical state parks to charming downtowns, these small towns in Florida demonstrate the diverse delights of the Sunshine State. Each presents a relaxed atmosphere with a slow pace of life that many vacationers long for. Whether you are planning to soak in the sun, indulge in sumptuous coastal cuisine, or explore rich historical heritage, you cannot go wrong with these Florida gems.

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