Autumn is a favorite season of many, with its irresistibly crunchy leaves, warm lattes, and adorable decorations. Even in The Sunshine State, which really puts the ‘sweat’ in ‘sweater weather,’ there are plenty of fun fall shenanigans to enjoy. If you’re looking for new places to explore this season, then check out these cute Florida cities and towns to add to your fall bucket list.

Florida’s old-world charm can be found all across the peninsula, already sporting the warm colors of fall. Rustic colors of reddish brick, faded wood, and dried green foliage paint these towns in perpetual autumn.

If you happen to visit on a cool day, all the better, then you can really play up the seasonal vibes with a hot latte and warm sweater.

While there are plenty of tropical and exotic sightseeing spots to visit around Florida, there are many places with a closer, homier feel, those of small towns, warm fires, and close company. These Florida towns are the perfect spots to visit this fall, from their storied history to their lively present.

So, grab your favorite travel buddy and check out these cute Florida towns this fall.

St. Augustine

Why You Need To Go: As the nation’s oldest city, this historic Florida town is a blast from the past, where old wonders like ancient forts, cobbled roads, and original architecture still live on today. 

Gulfport

Why You Need To Go: This hidden hippie town has all the groovy vibes, where you’ll find colorful cottages framed by Spanish moss, eclectic art on brick-paved streets, and some of the happiest folks around. 

Crystal River

Why You Need To Go: The best thing about fall in Florida is that you can still hit the water when it gets too warm, and Crystal River is the perfect place to do it, because you can even swim with manatees.

Dunedin

Why You Need To Go: Ring in fall with bagpipes and drums when you take a trip to the Scottish Highlands. Dunedin, which is the old Gaelic name for Edinburg, is the closest you’ll get without leaving Florida. 

St. Petersburg

Why You Need To Go: Warm your belly with traditional Russian food on the streets of St. Petersburg. Echoing the Russian city of its namesake, St. Petersburg still retains much of its European culture and inspiration today. 

Winter Park

Why You Need To Go: After browsing the bustling streets and window shopping through historic Winter Park, you can take the scenic route and cruise in a clear kayak through shady, winding canals at Winter Park Chain of Lakes. 

Happy fall adventuring!


Before you get going, check our Responsible Travel Guide so you can be informed, be safe, be smart, and most of all, be respectful on your trip.

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