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.

In a quiet corner of the largest island on Florida’s Gulf Coast, you’ll find Tarpon Lodge. Dating back to 1926, this old-school fishing lodge, now listed on the National Register of Historic Places, has seen several transformations over the decades, but today it’s back to its roots and better than ever.

Step inside one of Florida’s most storied stays. From its beginnings as a 19th-century general store to its transformation into a beloved hotel, this coastal icon has seen it all — fires, hurricanes, and decades of change. I’m taking you inside Jimmy Buffett’s favorite room, to the dining room where a legendary salad still lives on, and through the halls of the Island Hotel, which continues to charm travelers more than 160 years after it was built.

On the shores of Jacksonville Beach, Casa Marina Hotel has been a coastal landmark since 1925. With its Spanish-Mediterranean architecture and rich history, this intimate boutique hotel continues to welcome guests looking for a relaxing beachfront retreat.