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Aviles street shopping district in the Historic St. Augustine, Florida. Image credit Dennis MacDonald via Shutterstock

9 Timeless Towns In Florida

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.

With open Atlantic shores and the Gulf of Mexico, the sandy beaches with shopping and cute cafes in between complete every Florida vacation. Sebring is a south-central gem with an old soul, while Mount Dora is a hop from Orlando. Everglades City draws nature lovers to the national park, which was established soon after WWII. For old forts and lighthouses, you won't be remiss in either Fernandina Beach or St. Augustine.

Apalachicola

Dixie Theater in Apalachicola, Florida.
Dixie Theater in Apalachicola, Florida.

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 both 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, plus historic plaques throughout.

It's fun and easy to explore, with history woven into nature, like the dog-friendly Battery Park with a scenic pier. John Gorrie Museum State Park honors the life and the inventions of a local physician and air-conditioning pioneer. You can stop by Chapman Botanical Garden, take a fishing charter, or fish from the town's pier. And when the hunger pangs strike, the Up The Creek Raw Bar is an eclectic yet low-key spot with a patio overlooking the water. The nearby St. George Island Lighthouse Museum & Gift Shop is a reconstructed two-story lighthouse boasting panoramic ocean vistas. Hang around the beautiful beach on St. George Island before the 30-minute drive back to town over two spectacular causeways.

Brooksville

A gift shop in Brooksville, Florida.
A gift shop in Brooksville, Florida. Image credit Sunshower Shots via Shutterstock

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.

Just north, the prehistoric Chinsegut (ChinSEEgut) Hill and its 19th-century grand white-columned mansion look straight out of Gone with the Wind. Home to 20th-century suffragists and labor union activists, this historic site offers weekend tours plus hiking at Chinsegut Wildlife and Environmental Area. Next door, over 15,000 acres, Withlacoochee Forest, is a habitat with a pristine river for critical wildlife, with hiking, camping, and canoeing. The 46-mile-long Withlacoochee Trail is one of the best-paved bike trails in Florida. Detour through the shaded Dade Battlefield Historic State Park before the 30-minute drive back downtown to indulge in the Florida Cracker Kitchen. The original 1885 Brooksville Train Depot houses local history and railroad exhibits.

Cedar Key

The Sea Breeze Restaurant with a historic lighthouse in downtown Cedar Key, Florida.
The Sea Breeze Restaurant with a historic lighthouse in downtown Cedar Key, Florida. Image credit Nick Fox via Shutterstock

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.

From boating to birding and biking along the nearby trails, the natural isolation helps preserve the small town's traditional lifestyle and pristine environment. There is something for every taste, whether you are lounging at the Cedar Key Public Beach or spending a family day at the Lil Shark Park. Explore the closest islands with excellent beaches, like Atsena Otie, a ghost town with an old cemetery and ruins. If you are not staying at the historic Cedar Key Island Hotel on the main drag, the Cedar Key RV Resort and little light pollution are perfect for history under the sparkly night skies.

Everglades City

Old Collier County Courthouse in use as City Hall of Everglades City, Florida
Old Collier County Courthouse in use as City Hall of Everglades City, Florida.

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.

The Museum of the Everglades is an intriguing old laundry building with heritage displays of the Everglades area. The imposing national park to the south is a moving river of grass, which few know, whose dynamic environment is thrilling to explore, with trails and mangroves teeming with wildlife, including alligators. There are fishing charters and a tour agency for land and water adventures, with wildlife sightings guaranteed. Don't miss Triad Seafood Market & Cafe, a longtime favorite among tourists and locals alike. You can kayak along the beautiful Turner River, ride the airboats, and explore the nearby islands, like Chokoloskee. Its circa-1906 Smallwoods Store is a historic site under the original family's ownership, with provisions to picnic in the beautiful environs.

Fernandina Beach

The historic Prescott Building in Fernandina Beach, Florida.
The historic Prescott Building in Fernandina Beach, Florida. Image credit Dietmar Rauscher via Shutterstock

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 advance reservations. It's easy to connect to all the sites via great biking trails.

To the north, Fort Clinch State Park boasts sprawling oaks and a broad, beautiful beach at a circa-1864 fort site overlooking Georgia's coastline. Enjoy kayak lunches, wildlife trails, and camping. The intact 1800s fort offers tours of its barracks, prison, and blacksmith’s shop, plus re-enactors and monthly cannon firings. Nearby, the aptly named "Boneyard Beach," with driftwood on pristine sands is a hounding ground among photographers. Nearby, Little Talbot Island offers serenity as one of the state's last undeveloped barrier islands, with five miles of white sand beaches, maritime forests, dunes, and salt marshes.

Micanopy

Early evening photograph of Herlong Mansion in Micanopy, Florida.
Early evening photograph of Herlong Mansion in Micanopy, Florida. Image credit H.J. Herrera via Shutterstock

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.

The Micanopy Fall Festival awakens the sleepy town on the weekend before Halloween, perfect in time to visit the very old cemetery. The festival has been a homegrown affair for well over half a century, with 30,000 visitors and 200 vendors of arts and crafts, antiques, plants, and cuisine. Pearl Country Store & Barbecue is popular any day to stock up for a picnic along the shores at Tuscawilla Reserve. Explore Marjorie Kinnan Rawlings State Park or the nearby Paynes Prairie State Park with wild horses, bison, and other wildlife. Complete the Micanopy experience sipping a beverage at an oak-shaded café along Cholokka Boulevard, like Old Florida Cafe.

Mount Dora

The colorful downtown area of Mount Dora, Florida.
The colorful downtown area of Mount Dora, Florida. Image credit Jillian Cain Photography via Shutterstock

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.

You can visit Trout Lake Nature Center, explore Seminole State Forest just east, or bike along the shores to other lovable towns. The exquisite Mount Dora canal connects the kayakers to over 130 miles of navigable waterways, including the Wekiva River. Drive south to one of the state's most beautiful historic mansions. The Howey Mansion hosts events on historic estate grounds, a magical place to photograph and tour the creation of an Austrian artisan, from its massive front door to the foyer with curved walls of Florentine marble that appears to be one mass, and up the gracefully curving wide stone stairway with a wrought iron banister to the second floor.

Sebring

Local shops in Sebring, Florida.
Local shops in Sebring, Florida. Image credit Felix Mizioznikov via Shutterstock

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.

Wrapping around Lake Jackson, Sebring is a fascinating small town with an old soul, where people enjoy golfing, hiking, and waterfront recreation. The blend of history and nature awaits you for a memorable getaway in south-central Florida, just 70 miles southeast of Tampa. When visiting for the 12 Hours of Sebring in March, an annual sports car endurance race, the weather is great to stay at the popular Bonnet Lake Campgrounds on a budget next to a scenic pier. Although a newer cultural addition opened in 1998, the Military Sea Services Museum honors the Navy, the Marines, and the Coast Guard with exhibits. Minutes south, Lake Placid Tower is another historic landmark.

St. Augustine

Shops and inns line St. George Street in St. Augustine, Florida.
Shops and inns line St. George Street in St. Augustine, Florida. Image credit Sean Pavone via Shutterstock

St. Augustine is the nation's oldest European settlement. Many associate the city with Ponce de Leon's Fountain of Youth, named after the first Spanish explorer claiming Florida for Spain in 1513. He moved on in his pursuits, but 52 years later, Pedro Menendez de Aviles settled with 800 Spaniards near a large Native American village, officially establishing St. Augustine in 1565. Take a student-led tour of Flagler College, named after railroad magnate Henry Flagler, who first recognized the city had potential as a travel destination. Families enjoy Ripley’s Believe It Or Not, a museum, while The Lightner Museum showcases American Gilded Age pieces in the historic Hotel Alcazar.

Making your way over to the cooling waterfront, Florida's sun reflects off some of the nation's oldest buildings through the brick-lane historic district. A single ticket for the Old Town Trolley Tours is valid for three consecutive days. It's a great way to scope out the beauty aboard a narrated ride with 22 hop-on-hop-off stops. Next to the Old Town area, the Castillo de San Marcos's size matches its monumental significance and wide perspective of Matanzas Bay. Built from 1672 to 1695, the oldest masonry fort in the US recreates the past with cannon firings and demos on weekends, plus daily historic re-enactments. Anastasia Island offers broad beaches, camping, and a popular amphitheater.

Florida is steeped in sunshine and rich history. From the prehistoric Chinsegut Hill and its exquisite mansion in Brooksville to the nation's oldest town, St. Augustine, it is a fun hustle to discover a new town in a tropical paradise. Cedar Key's longest history and the most artsy ambiance out of all the keys make it among the best old towns in Florida for a quiet getaway.

Fernandina Beach is one of the northernmost old towns in Florida, overlooking Georgia with a beach and a fort at the historic Fort Clinch Park. Mount Dora is among the most gorgeous old towns in central Florida, while Micanopy flaunts historic inns and the famous Cholokka Boulevard. So, unearth the past and explore Old Florida through its timeless towns.

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