St. Augustine — the oldest continuously occupied European-founded city in the United States, dating to 1565 — sits on Florida's northeast coast. Jacksonville International Airport (JAX) is the closest major airport, about 45 minutes north by car; there's no direct commercial service into St. Augustine itself.
Hurricane season runs June through November
Like the rest of the Atlantic coast, St. Augustine takes hurricane season seriously, with the city publishing its own evacuation routes and storm updates. If your stay falls in this window, ask the owner directly what their storm policy is — some of the barrier-island neighborhoods here are also flood-prone even outside of a named storm, so it's worth asking about flood history specifically, not just hurricanes.
Historic district charm comes with historic district parking
The oldest streets downtown were laid out for foot and horse traffic, not modern cars — parking near the historic core is limited and often paid, even for residents. If you're renting downtown or in Lincolnville for a month or more, ask the owner about parking specifically; it's a bigger daily annoyance here than in most towns this size.
Getting your bearings
Historic Downtown puts centuries of architecture, restaurants, and shops on foot, with the tourist crowds and parking squeeze that come with it. Lincolnville, a half-mile walk south, was founded by freed slaves in the late 19th century and remains one of the most historically significant African American neighborhoods in Florida — walkable to downtown, with more of a lived-in, residential feel. Davis Shores, across the Intracoastal on Anastasia Island, is a laid-back waterfront neighborhood a short drive or bridge crossing from downtown. Vilano Beach, on a narrow peninsula north of the historic district, gives you both the sheltered Tolomato River side and direct Atlantic beach access in the same small area.