The Stark Restaurant opened on Main Street in 1926 and made a point of advertising that none of its food was fried. According to a review in the Sarasota Herald on April 10, 1926, the restaurant had a “salad and sandwich room and, in the center of the room, daintier lunches may be quickly and neatly served. The kitchen is one of the best equipped in the state. A charcoal broiler has been installed...The owners were Misses H. and M. Stark [who] have been among Sarasota’s most progressive and prominent citizens and have been in the forefront of the city’s advancement in every possible way.” 

The Fountain Room in Owen Burns’ El Vernona Hotel offered fine dining as well as a dance floor. The Sarasota Herald reported that the hotel hired a world-class chef; in 1927, it introduced a series of “supper dances” featuring the El Vernona Dance Orchestra. John Ringling took over the hotel after the land boom, and renamed it the John Ringling Hotel. After his death, his nephew John Ringling North operated the hotel, removed the fountain and added circus acts.

Another site, currently occupied by First Watch at Five Points, was home to the Ponce De Leon restaurant, which offered an eight-course dinner for 75 cents.

The Plaza Restaurant opened on First Street in 1928, near Palmer Bank, and quickly became a gathering spot for Sarasota’s movers and shakers, including politicians, developers, financiers, artists and civic leaders. It later became the meeting spot for the Liars’ Club, a group of writers who gathered each week to play liar’s poker.

The Tip Toe Inn on South Pineapple Avenue offered steaks, fish, chops, pecan waffles, cold cuts, salads and a “blue-plate special.” For 75 cents or 85 cents, diners could order a fish or meat course, vegetables, dessert, coffee or iced tea.