Of course, you'd take caution anywhere you're unfamiliar - especially at night. That said, St. Augustine is a city that depends on its thriving tourism industry and much is done to ensure its visitors enjoy a safe trip. A busy, pedestrian downtown means your biggest concerns after dark will likely be the ghosts on your walking tour.
Pay parking - Historic Downtown Parking Facility (HDPF): The $10/day fee is not pro- rated, but this might make sense if you're arriving in the morning. It's the most convenient option if you're coming into town for sightseeing, as the Visitor Information Center is here, as well as the two main train/trolley tour companies.
Free parking (with purchase) - Old Jail: If you like the sound of the Old Town Trolley, they sweeten the deal by including all-day parking with your ticket.
Metered and other parking: If you've got the patience, there's a spot out there waiting for you. Try Avenida Menendez between the Fort and the Bridge of Lions. Just coming in for dinner? Street parking is free after 5 p.m. If you'd enjoy a quick stroll, you'll find free parking just five or so blocks into nearby neighborhoods. (Be sure to double-check any signs before walking away!)
Handicapped parking: See this PDF map to find the most convenient spot to your destination.
LIMITED MOBILITYIf a "very walkable" city isn't the best news you've ever heard - don't worry. Simply book a trolley tour (with free parking) and navigate that way. One of the tour companies offers wheelchair accessible tours, and our equipment rentals section provides contacts for renting motorized scooters. Trolley tours bisect popular St. George Street, with benches and rest-stops along the length of the mile-long street. You can walk as much or as little as you like.