Decades in, these beloved restaurants still serve regulars, gather memories and shape the region’s food culture.

Southwest Florida’s legacy restaurants aren’t just places to eat—they’re the institutions that shaped our dining culture and continue to gather generations in shared tradition.

Along the Gulf Coast, a handful of such restaurants stand the test of time. These institutions hold fast to the lore of times when Naples was a sleepy fishing town and Cabbage Key was an artists’ retreat. Their enduring appeal relies on a potent blend of nostalgia, reverence for the past and an unfailing respect for the loyal clientele that returns time and time again.

The Veranda may be where locals celebrate big moments, but Cabbage Key Inn & Restaurant is where they go to slip off the map. Only accessible by boat, the island has a rich history, populated by the Calusa, Cuban fishers, homesteaders, artists and even a Corning glass heiress throughout the centuries.

The Dollar Bill Bar at Cabbage Key. Photography by Brian Tietz

In 1944, Larry Stults bought the island and opened a small, invite-only inn with an informal restaurant. Subsequent owners had a more generous guest policy and obtained a liquor license, creating one of the region’s quirkiest and most iconic landmarks: the Dollar Bill Bar.

“When a dollar bill bought much more than it buys today, these old salts would come in and say, ‘If I’m out of cash next time I come in, I’m going to claim my dollar here on the wall,” second-generation owner Rob Wells III says. Photography by Zach Stovall

Already in place when the Wellses bought the island and inn in 1976, the tradition has become so popular that every inch of the walls and ceiling is now covered in bills. (Each year, more than $8,000 flutters to the floor and gets donated to local nonprofits.) Locals and visitors alike now boat over to the island for a drink, a cheeseburger and a chance to add a dollar to the collection.

This is an excerpt from an article by Samantha Garbarini originally published on GulfshoreLife.com.