Thirty-five miles to the south, in Lake Wales, is Lekarica Golf & Country Inn, formerly known as Highland Park, a residential enclave developed in the 1890s by a zealous entrepreneur named Irwin Yarnell. The developer eventually went bust, but his beloved Highland Park became Florida’s first golf community when the architectural team of Stiles & Van Kleek designed 18 holes on the property in the mid 1920s. During World War II, a labor shortage resulted in six holes being removed and replaced with orange trees. The Highland Park Club remained a curious 12-hole layout until 1994, when an investment group purchased it and restored the missing holes to original specs.

Despite an ownership and name change, Lekarica is unmistakably Old Florida. Step onto your screened balcony any morning and let a plume of orange-blossom fragrance overwhelm you as you gaze over gentle hills cloaked in that signature Florida fruit. Snuggled in a valley are the golf course and a cottage-like clubhouse. At first glance, the 6,116-yard track looks like a pushover, but a tour around it reveals surprising elevation changes, doglegs and narrow fairways.

Moving on, we reach Florida’s west coast and Clearwater, where the historic Belleview Biltmore is still an imposing grande dame after 105 years. The floors of this rambling Victorian structure creak, and vestiges like keyholes, transom windows and wide corridors (designed to accommodate hoop skirts) impart a pleasant, time-warp effect.

When railroad magnate Henry Plant erected the Biltmore—now the oldest wooden hotel in America—he had no plans for golf. But his untimely death in 1899 left the property to his equally ambitious son Morton, who in 1915 hired Ross to craft two courses. Ten years later, Ross added a third course, which today is the only one still connected to the Biltmore.

The 6,614-yard layout recently underwent a masterfully subtle facelift by Sarasota-based architect Chip Powell. The greens still invite bump-and-run shots, and the cross bunkering and rectangular tees that Ross favored have been faithfully enhanced.

This sentimental journey ends at the Bobby Jones Golf Complex in Sarasota, where 18 of the 45 holes are pure Ross. In 1927 America’s leading amateur golfer lent his name to what remains this city’s only municipal links. To play all 18 holes of Ross’ work here, you must tee it up on two venues—the back nines of the British and American courses.

Sarasota has a long history with the Ringling Brothers Circus and today is home to the John and Mable Ringling Museum of Art, an impressive complex that includes a circus museum and Cà d’Zan, John Ringling’s sprawling, 32-room mansion.

In the early days, the parcel of land across the street from the Jones Complex served as winter headquarters for the circus. Wild animals inhabited enclosures and open fields, and more than a few backswings were interrupted by a lion’s roar or a gorilla rattling its cage. Back then, Florida was a frontier for the novel and exotic, and golf was just a babe in the woods.