Our research is editorially independent but we
may earn a commission for purchases made through our links.
While St. Augustine usually gets all the attention from visitors because it is the oldest city in the U.S., there are plenty of off-the-beaten-path destinations that are also full of rich and interesting Florida history. Discover some of the Sunshine State’s top historical destinations where you’ll find charming architecture, warm hospitality, and quaint fishing villages that will make you feel like you stepped back in time.
One of the most beautiful towns in Florida, Mount Dora is a small lakefront town in Central Florida that became popular in the 1920s. Here you’ll find 19th-century clapboard houses and historical buildings amongst large canopy trees, antique shops, and quaint bed and breakfast inns. A former winter retreat for hunters and fishermen, President Coolidge, Eisenhower, Thomas Edison and Henry Ford all stayed at the quaint and still-operational Lakeside Inn.
Rustic charm at its finest, Apalachicola is a small fishing village in North Florida known for its friendly locals and world-renowned seafood. Located on Florida’s Forgotten Coast, the delightful small town has over 900 historic listings that include small cottages and beautiful stained glass churches, allowing it to gain a reputation for its well-preserved Old Florida vibes. You’ll be hard-pressed to find any traffic or noise in this area, as the close-knit community prides itself on maintaining its historic charm.
Consistently referred to as the “small town with a big heart,” Port St. Joe is a charming community located on the Emerald Coast. Here you find postcard-worthy views and a glimpse into Florida’s earliest history, as it is the birthplace of the state constitution. Browse the compact city that boasts a beautiful marina and a downtown lined with antique shops and Southern diners where you can indulge in some of the state’s freshest seafood.
Dripping with small-town charm, Amelia Island has a stunning landscape of Spanish moss, quaint bed and breakfast inns, and pristine unspoiled beaches. Located on Florida’s northernmost eastern border, this area boasts top-notch Southern charm. Take a horse-drawn carriage through the historic downtown of nearby Fernandina Beach or explore some of the unique landmarks listed on the National Register of Historic Places, such as the oldest saloon in Florida.
One of the best places to experience Old Florida, Cedar Key is a rustic town nestled on the Nature Coast that is known for its natural beauty and a laid-back community that embraces a slower-paced life. Settled in the 1840s, here you’ll find a lighthouse that guided merchant ships in the 1850s and a National Wildlife Refuge that President Hoover established in 1929. Formerly the second largest city in Florida in the 1880s, Cedar Key is a small town that attracts artists, writers, and tourists that want to relax and enjoy the simple pleasures in life.
The most highly industrialized city in the state before the Civil War, Milton is a small town lined with brick storefronts and affectionately referred to as the Canoe Capital of Florida. With a downtown that is listed on the National Register of Historic Places, Milton is among the oldest cities in the state. Back in the 1800s, the Blackwater River served as the main transportation for timber, lumber, and brick, but now you can visit historical attractions such as the 1912 Imogene Theater and L&N Train Depot.
Located in Florida’s Big Bend region, Steinhatchee is a small fishing town with a rich history. One of Florida’s first settlements, this area attracts nature lovers who enjoy quiet country roads, diverse wildlife, and abundant fishing opportunities. Often referred to as “The Best Kept Secret in Florida”, this quaint fishing village boasts a 19th-century ambiance with charming Victorian-style homes nestled beneath beautiful moss-covered live oaks.
Micanopy is the “Little Town That Time Forgot” with an eclectic mixture of rustic shops lining its historical downtown. The oldest inland town in Florida, many claim this small town has the perfect balance of humble vibes and friendly locals, inviting visitors to explore the beloved jewel of Alachua County. Named one of the “Cutest Small Towns in America” by Huffington Post, this picturesque small town prides itself on the preservation of its Seminole Indian historical importance and antiquing opportunities.
Standing strong as one of the last authentic fishing villages in the Sunshine State, Cortez is like a living museum with a dash of Southern charm. Here you’ll find fish houses that date to the original founding families, a gorgeous 95-acre wildlife preserve, and a Florida Maritime Museum housed in a historic schoolhouse from 1912. Visit this Old Florida treasure for some of Florida’s freshest seafood and pristine natural beauty.
You can’t discuss Florida history without shining light on the Nation’s oldest city, St. Augustine. Believed to be founded in the year 1565, St. Augustine is dazzled with Spanish architecture and historic sites, including Castillo de San Marcos. Combine that with a wealth of culture, even some of the most historic ghost tours in the nation, and you can’t go wrong with a visit to this fine city.