Facebook
X
Pinterest
Copy Link
Typically known for its year-round great weather, the Sunshine State is perfect for combining a history lesson with the great outdoors. Florida’s small, charming towns dot the coastline, horse country, and islands between state parks and nature preserves. These nine timeless towns glow with historic warmth. The endless sunshine reflects off of architecture on a stroll along the heated brick sidewalks to the waterfront or a shaded park.
Apalachicola
Perched on the knob where the river flows into the bay, Apalachicola is unapologetically traditional and free of overcommercialized “assets.” Instead of boring buildings and chain establishments, you will find pastel houses on stilts and local businesses with a loyal fan base of tourists and residents. Established in 1828 as Cottonton and incorporated as West Point, it was renamed Apalachicola in 1831. Today, one of the last remaining fishing villages offers to disconnect from reality, with the closest urban center being Tallahassee, which is about an hour and a half northeast. Starting inland along Scipio Creek Boardwalk, a wonderful hiking area, work your way over to the waterfront. The downtown is full of preserved and restored architecture and historic plaques.
Brooksville
Just 50 miles north of Tampa, this historic town is surrounded by forests, rivers, and some of Florida’s most beautiful springs. The great walking around town will keep you chasing after sights without the kitschy tourist crowds. From the blueberry farms in the countryside to the courthouse and statue of a Confederate soldier downtown, Brooksville reveals the rural and wild side of Florida. Find unique attractions nearby, as well as Old Florida vibes downtown, with historic buildings and grand live oaks. May-Stringer House displays artifacts and memorabilia in a Victorian home, with guided and ghost tours. Directly southwest, you can relax at the Weeki Wachee Springs and catch the famous historic Weeki Wachee mermaid show.
Cedar Key
Cedar Key was the second town established in Florida after St. Augustine. Having avoided too much commercialization and been named one of the 10 coolest towns in America, this is not your ordinary Old Florida town. The island escape boasts the most charming downtown, plus the longest history and the most artsy ambiance out of all the keys. Cedar Key Museum State Park reveals its former port town and railway significance alongside a restored 1920s home and a wildlife trail. Thriving at present as a leading producer of farmed clams, Cedar Key is the place to indulge in seafood. After a hike along the Cedar Key Railroad Trestle Nature Trail, dine at Steamers next to the scenic fishing pier.
Everglades City
Some 200 miles south of Tampa, Everglades City was founded in 1875, across the 10,000 Islands, to trade furs with Chokoloskee Indians. Many visit the historic fishing town for hikes, great paddling, and to eat stone crabs at the funky riverfront restaurants. Located at the end of the road on the Gulf Coast, it offers you the remote feel, ocean vistas, plus easy access to explore the state’s Ten Thousand Islands. Many enjoy a pit stop here at the base of the ambitious statewide road, the Tamiami Trail, which opened in 1928. The small town is home to under 400, which spikes to 3,000 during the peak season from Christmas to Easter, including the very popular Everglades Seafood Festival in February. Fishing is very popular, including tarpon, snook, mullet, stone crab, and spiny lobster.
Fernandina Beach
Amelia Island, the 1817 site of the Pirates’ Republic, is steeped in history. Perched at the farthest northeast tip of Florida, Fernandina Beach strikes a balance between new glam and tradition. Boasting one of the best-preserved downtowns in the state, Fernandina Plaza Historic State Park offers beautiful scenery and information plaques, plus Pippi Longstocking was filmed at the house across the street. Enjoy shopping, galleries, and many places to dine in Victorian architecture. The historic circa-1838 Amelia Island Lighthouse offers monthly guided tours with reservations. It’s easy to connect to all the sites via great biking trails.
Micanopy
Hidden 10 minutes off the I-75 expressway and 12 miles from Gainesville, Micanopy often feels forgotten. At just one square mile and 654 residents, it is as much about the pace as it is about the place here. The area is rife with Old Florida vibes, tangled in the moss-draped live oaks and soaked through historic buildings. Spend the weekend at the grand 1845 Herlong Mansion, a historic B&B along the main drag with an antique and gift shop. The historic district houses the notable Montgomery Wall Project and Micanopy Historical Society Museum. Perched on the northern shore of Tuscawilla Lake, you can explore the surrounding lakes.
Mount Dora
Tucked between Lake Dora and the larger Lake Eustis, Orlando’s northern suburb is easily overlooked amid the rolling hills. But with regular festivals and nature at the doorstep, Mount Dora is a cherished place for strolls under a canopy of live oak trees. Boasting one of the most charming downtown areas, come celebrate its heritage and more, like the upcoming Arts Festival in February or the Blueberry Festival in April. Grantham Point, a lighthouse, and Renninger’s Flea Market & Antique Center complement every history-centric getaway. The dog-friendly Trimble Park is popular for lakeside recreation with picnic and camping areas, a playground, trails, and docks.
Sebring
George E. Sebring, an Ohio ceramics manufacturer, laid out this town on a circular plan in 1911, which became the seat of Highlands County ten years later. Sebring today is the processing and shipping center for nearby citrus groves and cattle ranches. It is a popular destination to spend the golden years with easy outdoor access and iconic sites. Sebring is the closest town to Highlands Hammock State Park, one of the state’s best, with camping, wildlife trails, and an old-growth cypress swamp. The Sebring International Raceway is one of the oldest in the US, located at Hendricks Field, a former US Army air base, along with a regional airport and an industrial park.
St. Augustine
