15 Best Small Towns In Florida You Must Visit 

1. Anna Maria Island

Step back in time on this barrier island where strict regulations govern the type of buildings and businesses allowed. 

2. Fernandina Beach

This Amelia Island enclave on Florida's northeastern border boasts 13 miles of pristine beaches.  

3. Apalachicola

Book a room at an inn and learn about the local oyster, timber, and fishing history—or relax on miles of unspoiled beaches on nearby St. 

4. Rosemary Beach

Located off the famous Scenic Highway 30A is a hidden gem called Rosemary Beach.  

5. Seaside

Leave the car behind in this walkable and bike-friendly town in northwest Florida—named the prettiest town in Florida by Architectural Digest

6. Winter Park

North of Orlando, this arts and culture community offers a small-town feel outside of Disney's hometown. 

7. Naples

It's no wonder retirees flock here. You get pristine beaches and picturesque neighborhoods that instantly feel like home.  

8. Crystal River

Swim with manatees in this central Florida town beloved by nature-seekers.  

9. Palm Beach

Head to Palm Beach in South Florida if you want to feel a little fancy.  

10. Captiva

Sister to nearby Sanibel, this captivating isle on Florida's southwest coast offers biking, sailing, birding, and a variety of water activities. 

11. Fort Myer

Make your way to the Fort Myers River District for the small-town feel you're craving.

12. Matlacha

Part fishing village and part artists' enclave, this quirky community over the bridge from Pine Island is quintessential old Florida. 

13. Dunedin

The town's annual Scottish celebrations honor its heritage and history, as it was founded by two Scotsmen in 1899. 

14. St. Augustine

On the northeast coast of Florida sits St. Augustine—the oldest city in the U.S. Known for its Spanish architecture and irresistible charm.

15. Micanopy

Just 15 minutes south of Gainesville, this Seminole-named enclave features dozens of antique vendors on oak-lined Cholokka Boulevard.  

15 Best Foods and Drinks to Try in Florida