St. Augustine: A Guide for First-Time Visitors

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What’s America’s oldest city? It’s not Jamestown. It’s not Pensacola. It’s not Williamburg. It’s St. Augustine which boasts the title, chiefly for the fact that the city has been continually inhabited since its founding in 1565.

While plans to celebrate the city’s 450th anniversary will occur throughout 2015, this coastal city ranks as a top Florida vacation destination any year. Most visitors are surprised by the number of things to see and do—a rare abundance in a city of only 14,000 people. Thanks to the authentic charm of its historic district, Spanish architecture and proximity to sandy beaches, it has earned a quiet reputation as being a perfect weekend or week-long getaway for families, couples, photographers, beach lovers and history buffs.

Tours, Carriages and Trolleys

On your first visit to St. Augustine, one of the best ways to grasp the layout and timeline of the city is by purchasing a multiple-day, hop-on-and-off trolley ticket from Red Train or Old Town Trolleys. Seeking something a bit more personalized? Try a narrated horse-drawn carriage ride over the town’s cobblestone streets.

City Walks Savory Faire Culinary Tours are a foodie’s delight and the most decadent way to stroll through history. The two-and-a-half-hour tour stops at various restaurants and shops for delicious samples of the city’s wine and culinary heritage.

Teens won’t complain about the frightful fun of a ghost tour. Paranormal activity is everywhere. Explore the darker side of the Old Town, including its most haunted building, the “Old Jail.” Choose among a number of companies offering scary agendas such as the Ghosts and Gravestone Tour, Sheriff’s Ghost Walk and Creepy Crawl Haunted Pub Tour.

Historical Sites

Start to wind your way through St. Augustine’s history at the Castillo de San Marcos. Today a National Park Monument, the Castillo was built between 1672 and 1692 by the Spanish to protect St. Augustine from pirates and British invaders.

Gain a perspective on the past from costumed interpreters within the fort who re-enact cannon firings and National Park rangers who lead tours. Climb to the gun deck and peer out a bastion overlooking the sparkling Matanzas waterway, a view that has barely changed over the centuries.

Back from the Castillo, wander the town’s streets and discover 36 buildings of colonial origin still standing in the historic area. Aviles Street oozes Old World allure with narrow, connected houses, street-side bistros and balconies draped in ferns and flowers. The Spanish Military Hospital Museum on Aviles appeals to anyone interested in medicine; it’s an authentic reconstruction of a military hospital that stood there from 1784 to 1821. Since 1893, visitors have toured the Oldest House, or Gonzalez-Alvarez House, a site that has been occupied continually since the 1600s.

The St. Augustine Colonial Quarter brings the city’s Spanish and British heritage to life through interactive exhibits including a leatherworking shop, a blacksmith, an 18th-century Spanish home and onsite boat-building demonstrations. Kids dash to mount the 35-foot watch tower overlooking the fort and explore the grounds.

Ahoy, ye mates! Pirates ransacked and burned St. Augustine in 1668 (hence the subsequent construction of the Castillo). Every March a re-enactment of Searle’s Sack acts as a reminder of the bloody pirate raid, but all year, the Pirate & Treasure Museum pleases swashbucklers and other folk with one of the world’s largest collections of genuine pirate artifacts. Seek out the Discovery Drawers marked with skull and crossbones and hidden throughout the attraction. (Tip: Don’t miss Jack Sparrow’s sword). Meander down to St. Augustine’s marina, home to a replica pirate ship, the Black Raven, which sails twice daily with outings for families and a little bawdier sail for adults in the evening.

Hop back on the trolley for the Fountain of Youth Archeological Park, the area first explored by Juan Ponce de Leon in 1513. Adults come in hopes of renewal from the famed mythological waters while kids rave about the cannon firings. See the reconstructed 1587 First Mission Church and examples of historically correct Timucuan (Native American) structures.

Cross the Bridge of Lions and enter the 1874 Lighthouse and Keeper’s House, another authentic structure. Climb 219 steps to the top for a 360-degree view and learn about offshore sunken boats and the ghosts that are said to still haunt the place.

Henry Flagler brought his East Coast Railroad and the first tourists to the state. He chose St. Augustine to build his first Florida hotel and it’s still in use, but now as part of Flagler College. Historic Tours of Flagler College highlight the architecture of the former Hotel Ponce de Leon, a National Historic Landmark, built in 1888. The complex is considered one of the finest examples of Spanish Renaissance architecture. Tours begin in the grand lobby with its magnificent, 80-foot, domed ceiling supported by eight hand-carved, ornate oak caryatids. Visitors also stop in the dining room where 79 Tiffany stained-glass windows stream light onto beautiful murals. Tom Edison installed the electrical lighting. Notice the original hotel furniture and art, as well as personal photos and mementos from Henry Flagler and his family.

St. Augustine’s Lightner Museum (also near Flagler College) is a quirky museum showcasing American Victorian era pieces, housed within the former historic Hotel Alcazar. Another overlooked gem is the Cathedral Basilica, built between 1793 and 1797 and considered America’s first parish.

More to Explore: Beaches, Golf, Distilleries, Alligators and Art Walks

St. Augustine Beach is part of the fun of visiting the location. Enjoy the sun and surf anytime of the year, but early-morning walks along the sandy shores make fond memories. Need more beach experiences? Wind your way up the coast to Jacksonville or south to Palm Coast. There are world-class beaches in both directions along Highway A1A.

Golf, anyone? A short drive outside the historic district to the World Golf Hall of Fame will pique your curiosity about the sport. Browse through the locker room where each inductee displays items that tell his/her personal story. Ready to play the links? There are numerous golf courses within a short drive of St. Augustine; this is Florida, after all.

The Alligator Farm close to the town’s lighthouse is an accredited zoological park which imparts a fascinating lesson on Florida wildlife. Thousands of gators roam the grounds, and feeding times turn into the most popular demonstrations. There’s a zip line over the swampy habitat for those who dare.

During late winter and early spring, hundreds of wood storks, roseate spoonbills and numerous egrets return to nest at the Alligator Farm, and the return attracts photographers from the around the world for a rare opportunity to shoot up-close encounters with the birds.

The new St. Augustine Distillery sits in the old Ice Plant, not far from the old Ponce de Leon Hotel. Adults are invited to take a free tour of the distillery that includes vodka and gin tastings. The plant began making handcrafted vodka and gin in 2014 by distilling Florida-grown ingredients in small-batch, copper-pot stills. The adjoining Ice Plant Bar and Restaurant sells the liquor as well as offering a menu of farm-to-table dishes for lunch and dinner.

The first Friday of each month, serious collectors and casual browsers stroll along city streets and pop in to more than 20 galleries offering fine art, photography and funky gifts. Some galleries offer refreshments, artist receptions or live music, and all are free. Even parking is gratis at the San Sebastian Winery on King Street, another great spot to tour.

Plan Ahead: Seasonal Events and Attractions

Every September, Florida Living History, Mission Nombre de Dios and the Diocese of St. Augustine present the historical re-enactment of Don Pedro Menéndez de Aviles’ landing in 1565. Sept. 8, 2015, marks the 450th anniversary, and celebrations are expected to be the biggest ever.

More than 3 million white lights twinkle throughout the downtown district from Thanksgiving to the end of January. The holiday lights display has earned recognition: National Geographic named St. Augustine as one of its top 10 places to see holiday lights.