(a full-day and evening)
In the late 1800s Riverside was Jacksonville's newest and most prestigious suburb. Neatly arranged streets and spectacular views of the St. Johns River drew leading citizens here to build their dream homes. The influx increased after the great fire of 1901 destroyed much of downtown. Nationally renowned architects were commissioned to design homes reflecting the expansiveness of a prosperous age. When Avondale was developed to the south in the 1920s, it continued the theme of sophisticated charm established in Riverside. Today the two neighborhoods offer a rich architectural heritage in their homes, churches, schools and parks of every description. In recognition of its scenic and historic value, the entire area has been designated one of the country's largest National Register Historic Districts.

The morning begins at the Cummer Museum of Art & Gardens followed by a lunch at any one of many delightful cafes and tea houses in the historic Riverside neighborhood.

Take a driving tour of Riverside and reserve some time for a shopping stop at the funky stores of Five Points or the upscale Shoppes of Avondale. Visit the Museum of Southern History and hear tales of the old south as well as view memorabilia from the Civil War. As you leave the museum, head south on Herschel, left on San Juan and across the Ortega Bridge to the historic neighborhood of Ortega. After crossing the bridge, turn left onto McGirts Road and follow it around as it becomes Ortega Road. On Grand Avenue, don't miss the "Gangster House." It was believed that "Machine Gun Kelly" and his wife Kathryn rented the house for a short time in 1933 and left abruptly before a middle-of-the-night raid staged by local police.

View the beautiful homes that were built in the 1920s during the boom days of development. Turn right on Robert Gordon and then another right on Roosevelt Boulevard heading back toward town.

Complete the day by sailing aboard one of Jacksonville's sternwheeler paddleboats (The Annabelle Lee or The First Lady of Jacksonville) for a dinner-dance cruise along the scenic St. Johns River.