Florida  seems to reinvent itself on a daily basis, with bulldozers and construction cranes as much a fixture of the landscape as plastic pink flamingos and palm trees. Nonetheless, much of the state’s history manages to persevere, much to the chagrin of developers. This five-day itinerary focuses on the state’s evolution from vast natural landscapes and colonial exploration to tourist-baiting attractions.
Any tour of Old Florida should start in St. Augustine , the oldest continuously inhabited city in the United States. The compact and quite walkable Old City  is very well-preserved. St. Augustine not only gives insight into early Spanish rule in Florida, but the grounds of Flagler College—formerly the site of Henry Flagler’s first big venture in Florida, the Ponce de Leon Hotel—are ground zero for the state’s evolution as a tourist destination.
To get a glimpse at some really old Florida, head for Merritt Island National Wildlife Refuge , about 90 minutes south of St. Augustine via a scenic drive along State Road A1A. Although the refuge serves as a security buffer for the high-tech goings-on at Kennedy Space Center , the natural surroundings still look pretty much the same way today that they did millennia ago. There are few spots in Florida as beautiful or as well-preserved as this area, whether you explore the beautiful beaches, take a hike on the trails, or fish along Mosquito Lagoon.
From Merritt Island, it’s about an hour’s drive to old-school Orlando theme park Gatorland  to see a great example of a pre-Disney take on the idea of a tourist attraction. Nearby, the quaint and beautiful city of Winter Park  (about 30 minutes away, just north of Orlando ) proudly displays its historic architecture in the form of expansive mansions and the retail shops that line its brick-paved Park Avenue.
An hour away from Orlando, the lakeside city of Mount Dora  is, for many people, Old Florida personified. Although the city has few actual historic sights, its rural location and charming downtown area—filled with antiques stores—evoke the wholesome pace of the state’s interior, albeit with a dash of cosmopolitan flair.
Although it’s three hours away from Mount Dora and located approximately in the middle of nowhere, the Gulf coastal fishing village of Cedar Key is a must-see for those interested in glimpsing Florida’s past. The dockside shops and restaurants have a salt-worn atmosphere that reflects decades of daily service to the anglers who keep the marina area busy, while the small downtown boasts hotels and other buildings that have been in continuous operation for nearly a century.
Ybor City , 2.5 hours south of Cedar Key, is one of the oldest neighborhoods in Tampa , and although today it’s best known for its rowdy nightlife, its history as the cigar-rolling capital of the United States is omnipresent. Several cigar factories are still active, and the spacious brick warehouses, though excellent for nightclubs, retain their historic appearance. You can almost smell the redolent aroma of tobacco leaves emanating from the bricks. Many of the area’s ethnic enclaves had roots in Ybor, but the influence of early Cuban immigrants—including one Jose Martí, who rallied for Cuban independence in the factories of Ybor—is unmistakable.