The Deep South meets Florida in Pensacola – quite literally. The Alabama border is just a few miles down the road, and the city has the small-town friendliness and sleepy pace of its Southern neighbor. But Pensacola (or P'Cola, as locals say), keeps it colorful with lively beaches, a thrumming military culture and a sultry, Spanish-style downtown.
Visitors to Pensacola come for the all-American blue collar vacation experience: snow-white beaches, jam-packed seafood restaurants, and bars where beer flows like water. During March and April, things reach fever pitch when hoards of students descend for the week-long bacchanalia known as 'Spring Break.' Beware.
Visitors less inclined toward tequila shots and wet T-shirt contests will appreciate the city's cultured, historical side. Since Pensacola's permanent settlement was established in 1698, flags belonging to Spain, France, Britain, the Confederacy and the US have flown over the city, often more than once, hence the city's nickname, 'City of Five Flags.' Traces of the past are visible today in the city's architecture and numerous historical sites and museums.
Downtown Pensacola, centered on Palafox St, sits just north of the waterfront. Southwest of downtown, the Pensacola Naval Air Station has trained pilots since WWII, and the base's airmen and airwomen are an intrinsic part of the city's culture. Across the Pensacola Bay Bridge from downtown is the mostly residential peninsula of Gulf Breeze; continue south over the Bob Sikes Bridge (toll $1) to Pensacola Beach, the destination for most of Pensacola's tourists. So why not toss your sunscreen and a novel in your beach bag, and head across the bridge to join them?