Cabbage Key: The Island Hideaway Wallpapered in Dollar Bills

Reachable only by boat, tucked into the islands of Pine Island Sound, Cabbage Key is one of those magical Old Florida hideaways that feels a world away from the mainland. And its cozy inn has one of the most unusual interiors you will ever see.

The island sits atop an ancient shell mound built up by the Calusa people long ago, which gives it a rare bit of elevation above the surrounding water. In 1936 and 1937, Alan Rinehart, son of the mystery novelist Mary Roberts Rinehart, built a winter home on the high ground with his wife, Gratia. That house is now the inn.

Step inside the restaurant and you will find the walls, ceiling, and rafters covered in thousands upon thousands of signed dollar bills. Nobody on the island knows who put up the first one. The bills that fall off are gathered up and given to charity.

Cabbage Key is also wrapped in legend as a possible inspiration for Jimmy Buffett’s song Cheeseburger in Paradise, a claim the island happily embraces with its famous burgers.

There are no cars and no crowds, just a few cottages, a water tower to climb, and Pine Island Sound all around. Cabbage Key is the kind of place you reach by boat and leave reluctantly, a little slice of timeless island Florida.