5 historic Florida restaurants you need to visit

Columbia Restaurant, Ybor City, Tampa. (Image via Facebook Columbia Restaurant)

By Crystal Harlan

April 12, 2024

If you’re hungry and a history buff, keep reading! Not only have these restaurants been around for decades, but their colorful stories alone are enough to warrant a visit.

Florida is known for pirates, Florida men, and other salty characters, so as you might imagine, the restaurants that have been serving these eccentric and adventurous individuals for decades are anything but boring. While some started as unassuming lunch counters and car-hop drive-ins, others operated brothels, illegal casinos, and speakeasies on the side. Despite decades of ups and downs, they’re still serving up food that keeps Floridians coming back.

1905: Columbia Restaurant, Ybor City

In 1903, Spanish-Cuban immigrant Casimiro Hernandez, Sr. opened a tiny saloon called Saloon Columbia, which quickly became a local watering hole for cigar workers in Tampa’s Ybor City. Just two years later, the saloon became a Columbia Restaurant. Over the years the restaurant expanded to occupy an entire city block, and today it holds the distinction of being both Florida’s oldest restaurant and the largest Spanish restaurant in the world. The 52,000-square-foot establishment has 15 dining rooms and can seat 1,700 customers. Spanning five generations of family ownership, this Tampa institution offers traditional Spanish and Cuban food, and hosts regular flamenco shows. Today, there are five Columbia Restaurants and two Columbia Cafes in Florida, including a location near Walt Disney World.

1913: Joe’s Stone Crab, Miami Beach

Joe Weiss opened Joe’s Stone Crab in 1913 as a small lunch counter, and today it’s a James Beard Award-winning restaurant. Politicians, actors, and athletes have dined here, and the restaurant has appeared in movies and books. The iconic joint is the biggest buyer of Florida stone crab claws, and serves them boiled, chilled and with its signature mustard sauce. In fact, Weiss helped raise stone crabs to delicacy status when he added them to his menu in 1921. His descendants operate the Miami Beach institution today.

1928: Cap’s Place, Lighthouse Point

Established in 1928 as a speakeasy, casino, and restaurant, Cap’s Place is the oldest restaurant in Broward County. The original owners, Cap and Lola Knight—who were rum runners during the prohibition—, and Al Hasis, originally named it Club Unique, and it quickly became known not only as an illicit establishment, but also for its rustic ambiance, fresh seafood, and original dishes. Back then, the restaurant was accessible only by water, and guests had to flash their car lights to signal to an employee, who transported guests to the restaurant by rowboat. Despite its remote location, Prime Minister Winston Churchill and President Franklin D. Roosevelt dined here when they were meeting at the Hillsboro Beach estate of then Secretary of State Edward R. Stettinius for a series of secret war conferences in 1942. Other famous guests include Joe DiMag­gio, Susan Hayward, Jack Dempsey, George Harrison, and the Vanderbilt Family. Today the restaurant is run by Hasis’ descendants.

1936: No Name Pub, Big Pine Key

This restaurant has gone through a few iterations over the last eight decades since it first started as a general store and bait and tackle shop in 1931. In 1936, the owners added a small room onto the main structure, which became the restaurant and pub. Then in the late 1930s, an upstairs storage room was converted into a brothel in an attempt to attract more business. According to the restaurant’s website the brothel “failed after several years as the fishermen were reported to be better looking than the ladies.”

By the 1950s, the brothel, general store, and bait and tackle shop had all closed, leaving just the restaurant and pub, and it quickly became a popular Keys hangout. In the 1960s, two cooks from Italy joined the restaurant, and to this day you can still order pizza made with their original recipe. During the 1970s and 80s, “there was a lot of illegal money passing through the Keys back then, and everyone loved to spend it. They had so much money in fact they started hanging it on our walls, and another tradition was born,” the website says. The interior of the No Name Pub pub is still covered with thousands of dollar bills.

1939: Jerry’s Drive-In, Pensacola

Known for its Southern homestyle cooking and affordable prices, this restaurant has been a staple in the community since it opened in 1939. Jerry’s Drive-In was founded as Jerry’s Barbeque by Jerry Glass, and at one point had a car-hop style service in the back. It was sold to Raymond “Grandpa” Wessel in the 1950s, who along with his son would wear white shirts with red Southern colonel ties. “When we first come here, we found out who everybody was,” Wessel said in a 1992 News Journal interview.

The restaurant was sold to Jimmy and Pam Halstead in 1997, and the current owners have recently made a few changes, but preserved the restaurant’s vintage look to give customers a nostalgic feel.


RELATED: These are Florida’s most romantic restaurants, according to OpenTable


  • Crystal Harlan

    Crystal is a bilingual editor and writer with over 20 years of experience in digital and print media. She is currently based in Florida, but has lived in small towns in the Midwest, Caracas, New York City, and Madrid, where she earned her MA in Spanish literature.



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