Almost anything you see or do in St. Augustine is a thrill for history and architecture fans alike. From the Colonial Spanish Quarter to the St. Augustine Lighthouse to the Fountain of Youth Discovery Park, you'll be reminded that Ponce de Leon founded this place 500 years ago (as of 2013). Even the museums, such as the St. Augustine Pirate & Treasure Museum, evoke a sense of living history through the immediacy – not to mention the ribald nature – of its artifacts.
Avoid: St. Augustine ghost tours, which are more gimmick than historic.
Historic St. Augustine, Florida's oldest city, has lodgings for every traveler, from family-friendly hotels to bed-and-breakfasts in preserved or renovated architectural gems. Whether luxury or budget, almost all are located close to the centuries-old downtown such as the Casa Monica, Autograph Collection, or along the wide, white-sand beaches, like the Saint Augustine Beach House. For longer stays or large groups, look into rentals of guesthouses.
Caution: The restored boutique hotels tend to have thin walls.
Avoid: Hotels that schedule evening weddings and other events, as the music can travel.
Pleasant, intimate and even exotic restaurants, many of them located in the old bay houses, make St. Augustine a dining destination for the culinary explorer. Flavorful international cuisine ranges from Cuban to Moroccan to Spanish. History buffs should be sure to visit the renowned landmark, the Columbia Rstaurant, a 100-plus-year-old Cuban-Spanish eatery, and Cafe Alcazar, which has been standing since 1888. If you're visiting on a humid summer day, don't neglect The Hyppo, which serves refreshing and delicious paletas (Mexican-style ice pops).
Be Sure to Sample: Local shrimp, black beans and rice, Cuban coffee, medianoche, stone crabs, conch fritters, chowder, grouper.
Nightlife in St. Augustine is more vibrant than you might expect from a historic district. Ranging from piano bars like Rhett's to brewhouses like A1A Ale Works (named for the beachside highway that travels up and down the coast of Florida), the venues offer everything from live music to home-brewed beer. Although not known as a live music town exactly, jazz is big here, with Stoogie's Jazz Club & Listening Room located in the old district near the bay, and the Cellar Upstairs Wine & Jazz Bar, located at San Sebastian Winery close to hotels and the airport.
Take It or Leave It: Thanks to the historic cigar factory, you'll smell smoke in bars all over town.
Of course, the nation's oldest city should be filled with antique shops, and St. Augustine is. In addition to antique, thrift and consignment shops, the Antique Warehouse, located between St. Augustine and Jacksonville, is like a superstore of collectibles. Souvenir and boutique browsing is best in Aviles and St. George streets in the pedestrian-only old city, where art galleries rub shoulders with natural apothecaries.
Avoid: Ponce de Leon Mall, anchored by JCPenney, unless you want to see a movie.
Best Local Souvenir: Antiques, crafts, arts.