One City Six Ways: St. Augustine, Fla.

Nicknamed The Ancient City and credited as being the oldest continuously occupied city in the United States, St. Augustine, Fla. is a beautiful, laid-back blend of Spanish Colonial architecture, historic sites, sandy beaches and ancient bricked streets.

History & Culture

A great way to get your bearings is to begin your visit downtown on St. George Street in the Colonial Quarter. From here, walk to the sprawling 17th-century Castillo de San Marcos on the waterfront and enjoy a tour of the oldest masonry fort in North America. Not to miss: the Gilded Age collection at the Lightner Museum, a climb to the top of the St. Augustine Lighthouse and a self-guided tour of the stunning Renaissance Revival Cathedral Basilica of St. Augustine, facing the Plaza de la Constitucion. You’ll also find a wide variety of galleries on the small streets leading off the plaza.


A walking tour with a food focus is absolutely the best way to get a great sampling of what the Ancient City has to offer in the way of Spanish-, British- and French-inspired fare. Choices include St. Augustine Food Tours & Tastings, City Walks Food & Wine Tours and The Tasting Tours.

© Elizaveta Galitskaya | Dreamstime


St. Augustine is a great cycling town. Bike rentals can be found at numerous locations with or without a guide. The city’s unique location also includes both white-sand beaches and a wide, deep inlet, making it perfect for water activities. Paddleboarding, snorkeling and swimming are popular pastimes, with equipment available at multiple locations throughout town. Consider taking a surf lesson from the local pros at The Surf Station, where experts are ready to help seasoned surfers find the best breaks or introduce beginners to this exciting pastime. Hikers will find beautiful trails through natural settings at area parks including Anastasia State Park, Fort Mose Historic State Park and Guana River State Park.


There’s a great selection of day spas in St. Augustine, including City Wellness, where yoga, acupuncture, spa therapies and health counseling are available. Prefer a resort setting? The Poseidon Spa at the historic Casa Monica Resort in downtown across from the beautiful Plaza de la Constitucion offers a full range of luxury services.


The narrow, shady streets of St. Augustine are ideal for a romantic escape (or escapade). Schedule a horse-drawn carriage ride in an open carriage where you can share a cozy blanket with someone special, while a guide shares the fascinating history of the city. Plan a tour and tasting at San Sebastian Winery, where you can extend your evening with wine, food, blues and jazz at the winery’s The Cellar Upstairs. Longing for a sunset? Book a private sailing tour of Matanzas Inlet. Multiple outfitters offer day and evening tours, some offering bespoke sailing with wine and snacks.

Family Fun

There’s a host of entertaining family activities to enjoy. Family favorites include the Alligator Farm Zoological Park, the Pirate & Treasure Museum, The Fountain of Youth, Ripley’s Believe It or Not Museum and hop-on, hop-off Old Town Trolley Tours.