Gil Hampton remembers witnessing the first dollar bill going up on the wall of the bar. There are many reasons why visitors have copied this action, with one myth being that fishermen left a bill to make sure they had money for their next next drink, but Hampton offers a more honest approach — “I’m not really sure.” Though the reasoning behind the first dollars may remain a mystery, the attractive aura of the Cabbage Key Inn and its famous Dollar Bill Bar are well known throughout the Pine Island Sound, and continue to draw big names and day trippers alike.
Measuring in at just over 100 acres, there is no need for cars on this Key. Instead, visitors and goods alike are transported solely by boat. Surrounded by ocean, the only source of freshwater is pumped from a well and stored in a historic wooden water tower that serves the inn and neighboring cottages through sunny skies and blistering hurricanes.
The Inn’s story on Cabbage Key begins with the purchase of the island by Alan and Gratia Hougton Rinehart in 1936. Alan was the son of famed author Mary Roberts Rinehart – often claimed as “The American Agatha Christie.” A force in her own right, Gratia was an heiress to the Corning Glass Works fortune. Together, they would construct a 4,500 sq ft winter estate on top of an ancient Calusan shell mound, making it the highest point on the key.
Like all estates, the property eventually landed into the hands of new owners, and they would convert the home into an inn by 1944 beginning the tradition of vacationers to Cabbage Key. Along with overnight stays for up to 25 guests, the renovated retreat offered boat-bound dinners, beach excursions to Cayo Costa, and even art classes, providing thousands of visitors the opportunity to enjoy the key for the first time.
It wasn’t until 1971 that the Dollar Bill Bar would open. With walls decorated from floor to ceiling with an array of currency, the bar has become the inn’s most iconic attraction. Ernest Hemingway, Katherine Hepbuurn, Ed McMahon, and Julia Roberts have all ordered a drink here. Jimmy Buffett loved the bar so much he invited the inn’s staff to one of his concerts. From bills signed by your everyday visitor to dollars bearing the ‘John Hancock’ of JFK and Jimmy Carter, it’s estimated that the bar’s walls hold around $70,000 (which could cover any fisherman’s tab). Due to tape mishaps or just the sheer number of bills, the bar does have a policy that any money that falls to the ground is donated to charity.
Though the island serves many day-trippers in the high season, the lucky few that stay at the inn enjoy the ominous presence of the island’s natural beauty and mangroves. With no pool or beach, it is a unique Floridian experience, giving guests many reasons to soak up the simple pleasures and joyfully “waste away again” at the Cabbage Key Inn.