Called the “Isle of Eight Flags” due to its strategic importance to a series of different governments, Amelia Island—and specifically the city of Fernandina Beach—never really came into its own until after the Civil War, when the last of those eight flags, the U.S. flag, began to be flown.

The shipping industry, and later a budding shrimping economy, grew up around the still-busy Fernandina Beach City Marina (1 S. Front St.). Across the street is the Old Railroad Depot (102 Centre St.), where shipped goods made their way into and out of Florida.

Walking along Centre Street, there’s a seamless blend of past and present, as many of the century-old buildings house shops selling antiques, art, books, and jewelry. Stop in for coffee at the Kozmic Kafe (13 N. 3rd St., 904/261-9910, 8 a.m.–5 p.m. Mon.–Sat.) for a mid-excursion pick-me-up, or drop by the historic Palace Saloon (117 Centre St., noon–2 a.m. daily), which has been serving up drinks to thirsty travelers since 1903.