swfl legacy restaurants ridgway bar and grill
Photography by Anna Nguyen

Where to Eat: Southwest Florida’s Best Classic Restaurants

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

by

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.  

Tony Ridgway sits in a chair by the front desk, greeting customers as they enter Ridgway Bar & Grill. The 80-year-old restaurateur has watched Naples’ culinary scene ebb and flow from this vantage point for half a century, since he moved his era-defining restaurant Chef’s Garden to the same building on Third Street South, and soon after, opened the popular Truffles on the second floor. “We were the first major restaurant on Third Street. In Naples, there was Piccadilly Pub, St. George and the Dragon, Kelly’s Fish House and Pewter Mug,” he recalls. “Truffles and Chef’s Garden really wrote the culinary standard until the latter ’80s.” 

A casualty of the times, both restaurants closed in the 1990s, and the building became Ridgway Bar & Grill in 2001. Two decades would be a major success for any restaurant, but the eponymous eatery is just one chapter in Tony’s legacy—a clear reflection of his love for American cuisine and French technique. 

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. 

“There are a lot of new restaurants that have a buzz,” Dan Groom-Traina, co-owner of The Dock at Crayton Cove, says. “I grew up going to The Dock. Our objective is to preserve the magic of one of the oldest restaurants in Naples.” Like Chef’s Garden, The Dock provided an infusion of much-needed excitement when it opened its doors in 1976. More than 200 people lined up to mingle over cold beers on the waterfront patio. Unpretentious and festive, it quickly became the heart of Naples’ social scene. Even today, mention The Dock to any longtime Neapolitan and they’ll wistfully recount stories about its heyday. 

Dan, alongside his father, Doug Traina, bought the restaurant from owner Vin DePasquale (who also co-founded Tin City) in 2019. They’ve made some modernizations, including building a chickee hut to cover the patio and updating the menu, but they’ve largely retained the essence of the original, including the famous Bloody Mary and Key lime grouper recipes. “I can’t tell you how many people have told me they had their first date at The Dock 35 years ago. It’s clear that we have a responsibility to the community,” Dan says. 

Kelly’s Fish House sits just upriver. Bob and Pat Combs opened the dining room in 1953 to feed crabbers and fishers unloading their catch at the family’s adjacent fishing operation. Current owner Kelly Ellis’ parents bought Combs Fish Company in the late ’50s, and by 1971, had taken over the dining room, renaming it Kelly’s after the family matriarch. The clientele has expanded over the years to include landlubbers seeking a taste of Old Florida. “In Naples, we are the last of the Mohicans as far as fish houses,” Kelly says. 

Out on the weathered deck or in the wood-paneled dining room where tables are inlaid with shells, life seems to move more slowly. Fresh seafood, including as much as 100,000 pounds of stone crab in season, is pulled from local waters by a fleet of 15 boats, overseen by Kelly’s son, Keith. Some of the catch is sold off, but much of it goes to Kelly’s, where it’s simply steamed, broiled or fried. “My father used to tell me, all fish is good as long as it’s fresh,” Kelly says. 

Tradition is also the guiding force at Farmers Market Restaurant. Like Kelly’s, it was born out of convenience—a stick-to-your-ribs Southern dinette to feed workers from the packing houses that dotted 1950s Fort Myers’ agricultural landscape. The Barnwell family took stewardship of the restaurant in the 1980s, but it was cook Olivia Williams, affectionately known as Ms. Libby, who was its heart. Her cornbread dressing, silky collard greens, old-fashioned sweet potato pies and stuffed bell peppers established Farmers Market as a local institution. “She was the Farmers Market,” Betsy Barnwell says.

After more than 40 years there, Ms. Libby passed away in 2019. The following year saw many of the remaining longtime cooks retire amid the COVID-19 pandemic, but the next generation of cooks has taken up the mantle, many of them trained by Ms. Libby herself to make each side, pie or tray of cornbread from scratch. “I was really lucky to have her,” Betsy says. “I was able to carry on her recipes. It’s all the way Ms. Libby taught us.” 

The Veranda carries a similar historic cachet in Fort Myers. In 1978, Paul Peden bought two turn-of-the-century homes and turned them into one of the few dining destinations downtown. Situated across from the courthouse, it was known as ‘Courthouse V,’ where lawyers hashed out deals over drinks. “We had a very active piano bar,” Paul recalls. “They came at 4 o’clock and stayed way beyond the time they probably should have. I knew everybody and they knew me.” 

The restaurant still has live piano, but over the decades, Paul has leaned into The Veranda’s reputation for special occasion dining. Anniversaries and weddings fill the reservation ledger, and career waiters pamper guests with old-fashioned service, tableside presentations and decadent housemade desserts. “We have a number of customers who come every anniversary or birthday,” Paul says. “People have booked for next Thanksgiving. They care enough to make a reservation a year in advance.” 

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. 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. 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.