Most people picture beaches when they think of Fort Myers, but I discovered that the historic downtown showcases a completely different side of this beautiful corner of Southwest Florida. Get ready to be impressed by Fort Myers’ River District, where palm-tree-lined streets, brick roads, and historic buildings are now home to lively shops, restaurants, and bars.

If you’re looking for a quiet corner of Old Florida, you’ll find it tucked along the Withlacoochee River in Levy County. Yankeetown is one of the smallest communities in the state, and it’s as peaceful, charming, and laid-back as they come.

Boca Grande, on the south end of Gasparilla Island in Lee County, takes some effort to get to because you don’t just pass through, you have to go there on purpose. And when you arrive, you’ll find an island community unlike anywhere else in Florida.

Now in its 112th season, The Gasparilla Inn in Boca Grande on Gasparilla Island still feels like a hidden treasure. The “Grand Dame” of this quiet barrier island continues to hold onto its timeless charm while making a lasting imprint on the community.

A Key West icon is shining brighter than ever. La Concha Key West, now part of the Autograph Collection, recently completed a $35 million renovation that honors its storied past while introducing a fresh, elevated experiences. Set in the heart of Key West’s historic district, this legendary landmark puts you right in the middle of it all, with the buzz of Duval Street just steps away.

The most iconic place to stay in the nation’s oldest city is Casa Monica Resort & Spa. You wouldn’t know it now, but this luxury hotel has been overlooked, shuttered, and even used as a government building during its 130+ year history. Thankfully, in recent decades, it’s been restored to its original grandeur and is now one of the most sought-after places to stay in St. Augustine.