ST AUGUSTINE MAY BE called the “Ancient City” but you’ll find no dull gray here. America’s oldest city is bustling with the vibrant colors, sounds and tastes of a place in its prime. Past is present in the brick-lined streets winding between centuries-old buildings, many with Spanish colonial and Moorish influence. Horse-drawn carriages and hidden courtyards create a quaint European essence.
The trolley offers a convenient way to explore the city’s attractions. Climb the 219 steps of the St. Augustine Lighthouse for a spectacular view, then visit the Old Jail which looks much as it did 130 years ago, but without the unsavory inhabitants.
The sights of Gilded-Age hotels and stately castles blend seamlessly with the roar of cannon fire from Castillo de San Marcos, a fort that has rebuffed pirates and British soldiers for three centuries. The St. Augustine Pirate & Treasure Museum spins tales of the 1586 buccaneer raid led by Sir Francis Drake, who burned the city to the ground, and of Captain Kidd, the pirate who was hung twice because his noose snapped the first time.
Cousteau’s Waffle & Milkshake Bar, a pint-sized spot with a gallon-calorie menu, is the perfect sight-seeing rest stop. Try Think Calypso, a Key Lime pie in a milkshake or the Air Kentucky, a hand-spun butter pecan shake with maple syrup, candied pecans and bourbon whipped cream. If you’re feeling especially undernourished, the 22 extra toppings include candied bacon.
Don’t leave downtown without visiting St. Augustine’s thriving specialty and antiques stores, or boutiques tucked into converted Victorian homes. Local art and handmade crafts can be found in the art galleries on Aviles Street, the nation’s oldest street.