7 Most Beautiful Historic Towns in Florida

Although Florida is typically known for its endless sunshine, mild winter weather, and miles of sandy beaches on both the Atlantic Ocean and Gulf of Mexico sides, the southern state is also brimming with history. Florida is home to coastal St. Augustine, which was the first permanent European settlement in North America, as well as a rich Native American culture and Civil War history. Florida's small, charming towns, which are situated along coastlines, near swamps, and in horse country, tell the state's story with their historic building, unique attractions and landmarks, and nature reserves. 

Micanopy

Although Micanopy only encompasses just under two miles in the rural north central region of the state, it was named "One of the 10 Best Small Towns in Florida" by Travel and Leisure Magazine in 2023. What tiny Micanopy lacks in size it makes up for with its rich history, unique eateries serving local cuisine, antique shops, boutiques, and museums. Named after the Seminole Chief Micanopy, the town's quaint, historic downtown draws in visitors from all over year round. Visitors can stroll under massive oak trees dripping with Spanish moss, as they check out attractions such as the Micanopy Historical Society Museum, which is housed in a vintage brick building. Also located on Micanopy's charming main street, Lost Ark Antiques and Wren Wood Antiques sell treasures that reflect the town's lively past. When the weather is nice, you can meander through the Micanopy Native American Heritage Preserve, which is located on the grounds of a historic Native American village. 

Mount Dora

Tucked away in central Florida just about an hour from Orlando, pretty and quaint Mount Dora feels like a world away. The town, which is situated on scenic 4,500-acre Mount Dora, is known for its small town charm and rich local history. Founded in 1880, the town is home to an abundance of museums and historic sites, as well as independent boutiques, a thriving local art scene and galleries, and laid-back outdoor eateries. Visitors can a morning or afternoon exploring the Modernism Museum of Mount Dora, which showcases a large collection of Modernist art by iconic American artists. The Mount Dora History Museum is located downtown, and features a collection of artifacts detailing life in the town from the 1870s through today. Outdoor enthusiasts from all over trek to Mount Dora to experience its Old Florida charm, taking part in water activites such as skiing, boating and fishing. The town's historic Lakeside Inn is the longest continually operating in Florida, and make a great place to call home for a few days or even weeks while visiting. 

Flagler Beach

Beautiful Flagler Beach is a charming town with a retro flair on the state's Atlantic coast. Conveniently situated between St. Augustine and Daytona Beach, Flagler Beach gives visitors a chance to get away from it all while still enjoying an exciting, adventure-filled vacation. This coastal gem features a historic downtown filled with one-of-a-kind boutiques, art galleries, and a mix of both casual and gourmet restaurants. The Flagler Beach Historical Museum created a self-guided stroll through the town, celebrating its unique heritage and highlighting points of interest along the way. Dubbed the "Jewel of Florida's East Coast," Flagler Beach's lively history dates back to the early 1900s, when it became a town. In addition to historic attractions, this beach town offers plenty for outdoor enthusiasts to do as well. For instance, the Bulow Plantation Ruins Historic State Park features an almost 7-mile-long hiking trail through old-growth forests. Part of the trail traverses along an original Native American path. 

Fort Pierce

Although Fort Pierce is known as being a quaint fishing village on the Atlantic Ocean Coast, this beach town has many other activities, as well as a rich history, to offer both residents and visitors. The town's historic downtown is brimming with "Old Florida" charm, as well as modern-day boutiques and eateries. Built in 1923, the history-laden Sunrise Theatre treats entertainment to a variety of live shows, from theatrical to musical performances. Visitors can immerse themselves in local history by attending the Downtown Fort Pierce Art Walk, which takes place every third Friday. Other historic points of interest include the A.E. Backus Museum and Gallery, the Navy Seal Museum, and the Pineapple Playhouse, which was established in 1949. If outdoor recreation is more you thing, don't miss a trip to Avalon State Park, or Indian Hills Recreation Area. 

Key West

Known as the country's "Southernmost City" due to its location at the very tip of the Florida Keys, Key West has a tropical island feel and plenty of small-town charm. Whether you want to go diving, snorkeling, a chartered fishing tour or any other ocean activity, you'll find it in this sun-soaked town. In addition to miles of sandy beaches, a Caribbean flair, and a collection of quirky bars, boutiques and eateries, Key West is steeped in history. The tropical town has long been a respite for famous artists and writers, including Ernest Hemingway, whose former house is open for public tours. The Oldest House and Garden is also available for touring, and was built in a Bahamian style in the 19th Century. History buffs won't want to miss a trip the Dry Tortugas National Park, which features Fort Jefferson, a former Civil War prison. The park also offers opportunities for camping, birding, snorkeling, and other eco-adventures. 

Apalachicola

Perched on the shores of Apalachicola Bay, a Gulf of Mexico inlet, the small town of Apalachicola has drawn in tourists from all over for decades. Apalachicola is located on Florida's "Forgotten Coast," and is a friendly port town filled with seafood restaurants, unique shopping experiences, historic buildings, and an interesting maritime history. Although the town is now known as a modern arts and culture destination, it still retains its Old Florida charm. Apalachicola's historic district is packed with picturesque Victorian homes, many of which date back to the 1830s. Visitors are encouraged to take a self-guided walking tour through the district to view the historic buildings up close. The John Gorrie Museum State Park combines outdoor adventure and history, which features a replica of the first ice machine. The Raney House Museum and the Orman House Museum are other must-see historic attraction to see when visiting Apalachicola. 

Milton

The charming town of Milton, which is located just north of Pensacola in the state's panhandle region, is dubbed "The Canoe Capital of Florida" for good reason. The Coldwater, Sweetwater and Blackwater waterways meander through the town, beckoning paddlers from all over the country to visit. In addition to being a water-lover's paradise, Milton offers a rich local history and several must-see historical attractions. The town is situated on the 9-mile Blackwater Heritage State Trail, which is the ideal venue for walking, running, biking, and birding. History-loving visitors can also check out the Museum of Local History, which showcases the area's fashion and industry background. The West Florida Railroad Museum depicts Milton's exciting railroad history through exhibits, a historic freight and passenger depot, memorabilia, and model trains. 

The next time you find yourself traveling through Florida, take some time to explore its small, charming towns to gain an understanding of the important role the state plays in the country's history. Whether you prefer more tropical destinations, like the Florida Keys, or a quaint port towns featuring rich maritime backgrounds, you'll find it all in this southern state. You won't need to decide between the beach or historical attractions, as many towns feature both.