Nestled up against the Georgia border, this is a different kind of Florida than you may have experienced further south. Almost alone among Florida’s major cities, Jacksonville was never primarily a tourist destination. An important point for the railroads of David Yulee and Henry Plant, it made its mark as a working town—paper mills, a port, transportation hub and later an insurance industry town. The city’s districts are defined by the St. Johns River, which runs north into the city, then makes a right turn to reach the Atlantic Ocean at Mayport. Although it has beaches—both tourist-kitschy and pristine—at its doorstep and elegant resorts, it’s not a resort town. As a visitor, you’ll find yourself surrounded by residents when you go to area attractions and restaurants. If you decide to stay cloistered inside a visitors-only resort, you can do that, too.
3 Have a “sundowner” at the Penthouse Lounge atop the Casa Monica Hotel overlooking the ocean. You can stay on for dinner if you’re too tired or buzzed to drive; if you aren’t drive into downtown and have dinner at Matthew’s.