13 Prettiest Small Towns In Florida
While Florida’s retirement reputation is largely linked to its tax benefits, retirees will tell you the true ecstasy lies in the sunshine, warm weather, and breathtaking scenes. From its turquoise waters to its storybook downtowns, Florida’s beauty draws travelers, vacationers, and retirees like flies to honey.
With 175 state parks, over 9,200 miles of trails, and the longest coastline in the contiguous United States, the Sunshine State is undoubtedly home to some of the prettiest small towns in the country. Coupled with engaging festivals, bucket list-worthy excursions, and some of the oldest historic landmarks in North America, these Florida towns invite you to experience charms and create lasting memories at a slower pace.
Key Biscayne
Affectionately dubbed an “Island Paradise,” Key Biscayne is a tropical retreat sheltered from the buzz of nearby Miami. Formerly a coconut plantation, today the palm-lined barrier island village is known for its beaches. However, before you enjoy these sugar-sand shores, the journey into town is just as beautiful as the destination. With panoramic views of the Miami skyline and ocean views on either side, crossing the Rickenbacker Causeway sets the stage for even more beauty to come.
Once you reach Key Biscayne, the dilemma comes of where to go first. Windsurf enthusiasts and beachgoers traveling with four-legged friends flock to shores like Hobie Beach, a beautiful dog-friendly shore offering windsurfing rentals. Alternatively, Bill Baggs Cape Florida State Park is known for its Atlantic views and recreation. Guests can climb the historic 1825 Cape Florida Lighthouse for jaw-dropping vistas overlooking Biscayne Bay or enjoy a more leisurely lie in the sand. Swimming, kayaking, and bicycling are other popular activities, with a 1.5-mile paved path winding through the park.
Islamorada
Tropical beauty extends to Islamorada, a village of islands spanning six of the Florida Keys. Local legends say that the name Islamorada comes from Spanish explorers who once called it “isla morado,” or “purple island,” for its lilac skies. These watercolor sunsets can still be enjoyed today, whether booking an Islamorada Sunset Cruise with Sundance Watersports or enjoying a beach day at Founders Park.
For a more secluded day in this tropical paradise, some parts of Islamorada can only be reached by boat or paddle. Lignumvitae Key Botanical State Park is one of these places, with a gorgeous canopy of virgin hardwood hammock and surrounding turquoise waters. Travelers can reach the Lignumvitae Key through locales like Robbie’s Marina, which offers kayak rentals and a ferry service on Fridays and weekends. The island is great for swimming, snorkeling, and exploring on a self-guided tour, its shaded paths revealing wildlife like Liguus tree snails and rare butterflies like the Florida purplewing.
Crystal River
Wildlife spotting is equally enchanting in Crystal River, “the Manatee Capital of the World.” As one of the only places in Florida where travelers can legally swim with the lovable sea cows, this western Florida town attracts animal lovers worldwide. Every winter, anywhere from 500 to 1,000 manatees migrate here, escaping the colder waters elsewhere in the Gulf of Mexico (America), making this Crystal River’s busiest tourist season.
During this peak manatee season, from November 15th through the end of February, Paddles Outdoor Rentals And Tours offers their iconic Swim with Manatees Tour. They also offer a Clear Kayak Manatee Ecotour from November 15th to March 31st, showcasing the gentle giants in Crystal River’s prettiest waterways. The town’s famous blue-green waters can also be enjoyed at spots like Three Sisters Springs, a scenic section of the Crystal River National Wildlife Refuge. Encompassing 20 islands in and around Kings Bay, the refuge is one of Florida’s prettiest natural attractions.
High Springs
About an hour-and-a-half north of Crystal River, High Springs is another Florida town known for its vibrant turquoise waters. Unlike the coastal manatee capital, the town is located further inland. Its natural springs, bright blue and clear like those in Crystal River, are protected in Florida's newest addition: Ruth B. Kirby Gilchrist Blue Springs State Park. Privately owned until 2017, the 400-plus-acre area became Florida’s 175th state park, named after its former owner. Today, its enchanting waters and landscape can be enjoyed by all.
The largest of its springs, Gilchrist Blue, is where visitors can swim and snorkel in crystal-clear waters. It generates an average of 44 million gallons of water per day, which flows to the Santa Fe River. The four smaller springs can be enjoyed from land along the park’s serene nature trail. While it is less than a mile long, the short hike offers extraordinary sights and scenes, including a towering 350-year-old cypress tree. Along the wooded path, you will also encounter hidden springs, sandhills, and spider lilies underfoot if you visit early in the year.
Cedar Key
Returning to the beautiful Gulf Coast, Cedar Key is an island town frozen in time. Named after its once-abundant cedar trees, the former lumber town is now known for its history and natural beauty. Located around three miles off mainland Florida, seclusion has allowed the historic town to preserve much of its Old Florida architecture. Many of its buildings span the 19th and 20th centuries, including the 1870 Lutterloh House, now the Cedar Key Historical Society Museum.
Preservation extends to Cedar Key’s natural splendor. The Nature Coast town offers some of Florida’s prettiest unspoiled landscapes, including those at the Cedar Keys National Wildlife Refuge. The 13-island refuge, accessible by boat or paddle, is a haven for wildlife spotting. Manatees and dolphins can often be spotted just offshore, while bald eagles and shorebirds fly overhead. Whether booking an excursion with Cedar Key Boat Rentals & Island Tours or exploring the islands solo, the Cedar Key refuge is the perfect place to experience Florida’s wild side.
New Smyrna Beach
If a vibrant beach culture is more your vibe, New Smyrna Beach boasts some of the prettiest shores in Florida—17 miles to be exact. Bordered by the mighty Atlantic, New Smyrna's beaches boast different atmospheres. While dog owners flock to shores like Smyrna Dunes Beach, the Canaveral National Seashore attracts nature lovers. Preserving dune, oceanfront, salt marsh, and lagoon habitats, Canaveral shines as the “Longest Stretch of Undeveloped Atlantic Coastline in Florida.” By sheltering the seashore from development, thousands of plant and animal species thrive here, including Oak Hammock and sea turtles.
For a more social day in the sand, the Flagler Avenue entrance is a well-known shore beloved by surfers. Noted for its “consistent swells,” Southern Living named New Smyrna Beach “One Of The Best Places To Surf In The World” in 2025. Flagler Avenue also offers beach wheelchairs and accessible ramps, making it a popular beach for sandcastle building and lounging. Accessibility is a key feature at Smyrna Dunes Park as well, where coastal scenes can be enjoyed from a wheelchair-accessible 2-mile boardwalk.
Sanibel
Beachgoers with a passion for shelling may prefer Sanibel, a barrier island town famous for its shell-dotted shores. Located in southwest Florida, just 12 miles long and 3 miles wide, Sanibel Island is a small but breathtaking tropical oasis. With its curved shores, the island is a magnet for over 400 species of sea life and shells, washed ashore from the Gulf of Mexico (America). Shelling is so popular here that locals have even adopted a quirky phrase to describe the bent-over search: the Sanibel Stoop.
Lighthouse Beach is one of its prettiest shores and best shelling spots, with scattered whelks and cockles. Views of the 19th-century Sanibel Lighthouse also make for the perfect photo op. Other popular shelling shores include Bowman’s Beach, whose soft sands and gentle waves make it ideal for families. It also offers a few short hiking trails.
However, nature lovers will also want to check out the J.N. “Ding” Darling National Wildlife Refuge. Covering about half the island, the refuge is famous for its diverse wildlife, from pelicans and Roseate Spoonbills to manatees and dolphins. For the best wildlife spotting, guests are encouraged to explore Wildlife Drive, the Observation Tower, and the Wildlife Education Boardwalk.
St. Augustine
Although St. Augustine is a gateway to pristine shores like Crescent Beach and St. Augustine Beach, this “Ancient City” is even more renowned for its fabulous past and jaw-dropping architecture. Claiming itself as “the Nation’s Oldest City,” the Spanish-founded town has roots dating back to 1565, housing some of the oldest sites and landmarks in the country. For travelers looking to step back in time to opulent Old Florida, there is truly no better place than St. Augustine.
Many like to begin their St. Augustine adventure on the shores of Matanzas Bay, where Castillo de San Marcos dominates the landscape. Built between 1672 and 1695 from coquina extracted from Anastasia Island, it is the oldest masonry fort in the continental United States. Deeper inland, other imposing architecture in St. Augustine includes sites like the Lightner Museum, housed in the former Hotel Alcazar. The Spanish-style Cathedral Basilica is equally staggering, claiming to be the nation’s first Catholic parish.
Nearby, Villa Zorayda is another must-see museum. Built in 1883 as a private residence for an eccentric billionaire, the striking structure was modeled after a grand 12th-century Moorish Alhambra Palace.
Micanopy
Contrasting the lavish landmarks of St. Augustine, Micanopy showcases Florida’s humbler past. Modest by comparison, but no less beautiful, many recognize Micanopy as Florida’s oldest inland town. Established in 1821, it is often referred to as “the little town that time forgot” due to its frozen-in-time charms. Cholokka Boulevard is one of the prettiest places to see this historic preservation, the street punctuated with old oaks draped in webs of Spanish moss. But even greater beauty lies beneath, its antique storefronts and buildings worn by time but beautifully preserved.
Inside these aged main street structures, visitors can find an eclectic range of attractions and businesses, including the Micanopy Historical Society Museum. Further south, visitors will also see why Micanopy calls itself the "Antique Capital of Florida.” Cholokka Boulevard has an incredible concentration of antique shops, including the Micanopy Trading Outpost, the Shady Oak Gallery, and Delectable Collectables, to name a few. Nearby, the Old Florida Cafe is the perfect pick-me-up or prelude for hours of strolling and shopping.
Mount Dora
About an hour-and-a-half southeast of Micanopy, Mount Dora is another quaint inland town with laid-back attractions. Set in central Florida, much like Micanopy, the town is an antique hotspot. Three times a year, Mount Dora hosts an Antiques and Collectors Extravaganza, with 800 different vendors. For the remainder of the year, the Village Antique Mall and Renninger's Flea Market & Antique Center attract treasure hunters from across the country.
Mount Dora’s year-round charm also extends to Lake Dora, whose 4,000 acres can be enjoyed from Grantham Park or explored on exciting eco-tours. Tour operators like the Rusty Anchor offer Mount Dora Sunset Cruises for scenic skies and tranquil views. Alternatively, wildlife viewing and enchanting scenes can be enjoyed on their Dora Canal Tour. The cruise takes visitors through a bewitching cypress swamp, echoing with singing shorebirds. Down below, you may also see its waters rippling with alligators, gliding just below the surface.
Fernandina Beach
Back on the Atlantic coast, Fernandina Beach blends a colorful past with breathtaking natural scenes. The Amelia Island town, first inhabited by the Timucua tribe, went on to fly eight national flags. Beginning with France in 1562 and ending with the United States, this earned it the nickname "Isle of 8 Flags.” Visitors can learn more about these eras at the Amelia Island Museum of History, located in the 50-block Fernandina Beach Historic District.
To experience Fernandina Beach’s famous blend of history and nature, make sure to set aside time for Fort Clinch State Park. Guests can explore the rooms and galleries of a pre-Civil War fort to learn more about Fernandina’s political past. Afterward, the 1,400-acre park beckons with its expansive trails and beachfront. Oak-shaded bicycle tours are a popular way to take in views, while hikers can enjoy scenic paths like the Willow Pond Nature Trail. For fun in the sand, the park also boasts three sections of coast, offering shark tooth hunting, swimming, and dolphin sightings.
St. Pete Beach
For beachgoers seeking Florida’s classic resort-style atmosphere, St. Pete Beach is one of the prettiest and liveliest Gulf Coast towns. Occupying the barrier island of Long Key, this coastal town attracts visitors with its postcard scenes and year-round sunshine. Emerald waters and powder-white sands can be savored at shores like Upham Beach Park, while its tucked-away “Secret Garden” is the perfect place to escape summer crowds.
Overwhelming crowds can also be avoided in Pass-a-Grille Beach, a St. Pete neighborhood known for its cozy coastal atmosphere. With the exception of the Paradise Grille, none of Pass-a-Grille’s buildings are built directly into the sand, allowing visitors to enjoy unobstructed sunset views. For a break from the beach, downtown Pass-a-Grille is the perfect interlude, especially on 8th Avenue. The charming strip is clustered with chic shops, cafes, and galleries like the Dody Beach Boutique, Paradise To Go, and A Little Room For Art.
Stuart
Voted the “Best Coastal Small Town” by USA Today readers in 2024, Stuart is a spirited seaside town known for its comfortable climate and maritime culture. Perched between the Atlantic Coast and St. Lucie River, life in Stuart is laid-back and easy-breezy. With an annual average temperature of 72°F, it is also easier to enjoy Stuart’s attractions without breaking a sweat. Whether angling aboard a Stuart Fishing Charter or sightseeing on a Treasure Coast River Cruise, your time in this “Sailfish Capital of the World” is all about embracing leisure.
For a beachy outing, Bathtub Beach is one of Stuart’s prettiest shores. Its offshore reefs are multi-purpose, sheltering the shore from wild waves while also drawing snorkelers and scuba divers to its wonders. For serene views of the St. Lucie River, the Riverwalk is another Stuart staple. The boardwalk connects visitors to sites like Flagler Park, Kiwanis Park, and Downtown Stuart, making it the perfect route for first-time visitors.
Discover Florida’s Prettiest Small Towns In 2025
While beauty is subjective, year after year, these pretty Florida towns attract retirees and travelers from all over the world. Whether visiting historic towns like St. Augustine and Micanopy for their architecture, coastal communities like Key Biscayne and Islamorada for their tropical beauty, or nature retreats like Crystal River and Cedar Key for their wildlife, beauty reaches through every corner of the Sunshine State. Although the title of “prettiest” may be subjective, each of these Florida towns is undeniably striking and memorable in its own way.
