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St. Augustine, the Old City

Stephen Brown

St. Augustine mapStep back in time in St. Augustine; the oldest continuously occupied European-established city and port in the continental Untied States. Nicknamed the Old City, St. Augustine is the gateway to Floridian history. Through the ages, St. Augustine has been settled by Timucua Indians, occupied by the Spanish (twice) and the British, and experienced bloody pirate raids. This has all culminated in a bloodied history and supposedly one haunted city. For those who are breezing through St. Augustine, make the most of your time with a list of attractions and hot spots to experience.

St. Augustine


Casa Monica Hotel - St. AugustinePlush Lodgings

Stay in style at the Casa Monica Hotel, a Kessler Autograph Collection property. Located in the historic district, the hotel itself is a landmark, built in 1888. Just off St. George Street, the Casa Monica is within walking distance of nearly everything in downtown St. Augustine, with the Lightner Museum and Flagler College just across the street, and Plaza de la Constitución, the city’s original town center, as designed by the first governor Gonzalo Méndez de Canzo in the late 16th century, a stone's throw from the hotel lobby. St. Augustine’s only AAA Four Diamond hotel, the Casa Monica is flush with all the amenities one comes to expect from a destination that was once in the Henry Flagler portfolio. The dining at 95 Cordova is some of the best in the city, specializing in global cuisine with seasonal and local twists. For a more casual bite, Café Cordova embraces the European sidewalk café alfresco experience with New World flair. The gourmet pizzas are fantastic and light, the perfect light lunch. For a nightcap, the Cobalt Lounge has one of the most extensive martini menus in the city. 95 Cordova St., 904-827-1888,


The gilded history of St. Augustine, and a guy named Flagler

Lightner Museum - St. AugustineIf you seek the more aesthetic side of history, a visit to the Lightner Museum is a must. The museum sits in the former Hotel Alcazar, another former Flagler property (this guy really had a thing for hotels in Florida, huh?), and maintains the opulence that once dominated the Gilded Age. On exhibit is an extensive collection of 19th century artifacts of the truly well-to-do, complete with clothing and costume, furniture and home accessories, mechanical marvels of the day (phonograph anyone?), and art, all meticulously preserved and displayed as if you were visiting the Hotel Alcazar at the height of its prominence. 75 King St., 904-824-2874,

   Flagler College is in the heart of St. Augustine. Once the storied Hotel Ponce de León (another Flagler property), the National Historic Landmark built in the Spanish Renaissance style has become the centerpiece of the private liberal arts college, acting as dorms and dining hall for Flagler College students.Flagler College - St. Augustine Visitors can go on student-led Legacy Tours of the property (ticket prices help keep tuition costs down), who are well versed in the stories that once played out behind the gates of the old hotel grounds. The hotel, which was built in two years and opened in 1888, spared no detail. Artisans worked round the clock, creating a grand palace of the South, with the largest collection of installed Tiffany glass in the world (dining room, stained glass), beautiful mosaics (one tile with the likeness of Flagler is said to be haunted), gilded mirrors and remarkable murals covering the rotunda ceiling. The Hotel Ponce de León was to be the crown jewel of the American Riviera Flagler envisioned St. Augustine would become. 59 St. George St.


Get Piratical

St. Augustine Pirate & Treasure MuseumThe pirate life is something St. Augustine is no stranger to. Piratical raids, mutinies and a general lawlessness permeated the Caribbean and Florida coasts from the late 16th century through the early 18th century, and the St. John's River and St. Augustine were frequent stops of privateers, buccaneers and pirates. Names like Sir Francis Drake, who attacked and burned the town in 1586, and pirate Captain John Davis, aka Robert Searle, plundered the town, murdering any and all who crossed the raiders' path in 1668.

St. Augustine Pirate & Treasure Museum - treasure   In homage to St. Augustine’s rough and rowdy past, the St. Augustine Pirate & Treasure Museum, a mere 100-yards from the fort Castillo de San Marcos, is a swashbuckling good time. Blunderbusses and swords, and creaky planks adorn the museum, where interactive exhibits and historical stories give visitors a full-circle perspective on the darker side the region's early history. Kids and parents can climb onboard the deck of a pirate ship, fire cannons and try their hand at tying shipman’s knots, sit in the bowels of the Queen Anne’s Revenge, ship of the legendary Blackbeard, as he meets his end at the hand of British Lieutenant Robert Maynard. They can view the romanticized history of pirates on the silver screen and even see authentic booty recovered from pirate shipwrecks, and see one of the only surviving Jolly Rogers in existence. A must for anyone wanting to learn more about St. Augustine’s buccaneer past, and fun for the entire family. 12 S. Castillo Dr., 877-467-5863,


Haunted House

The Old City, which turns 450 in 2014, has had a rough and rowdy past. Death, destitution and hopelessness culminated in what is today one of the most haunted places in the country. Whether you are a skeptic, believer or simply non-committal, the spooky tales and haunted history of St. Augustine will have you riveted. And one of the best ways to hear those scary stories and see a different side of the city is through a ghost tour.

   Tours travel throughout the historic district either by foot, hearse or trolley, stopping here and there, relating the tales of residents long gone. It is a great way to experience the town at night, getting a greater sense of the history that made St. Augustine what it is today, as well as get to know fellow tourists and thrill seekers.

   For an added twist to the ghost tour, try the haunted pub tours. Within the historic district of Saint George Street, many of the restaurants and pubs are housed in the buildings or on foundations that have stood for centuries. The walking tours take groups from pub to pub where they can enjoy a few cocktails while listening to spooky stories about spirits that still linger. A great way to kick-start an evening on the town.

   The Original Haunted Pub Tour took our small group to Nick & Brad’s on Cathedral Place, Harry’s Bar and Meehan’s Irish Pub, both on Avenida Menendez, and finally to the Mill Top Tavern on St. George St. The tour lasted about two and a half hours, including a few chills and chilled libations. 904-824-8840,

Taco Shop - St. Geoge St. - St. AugustineLate-Night Snack   

After a night of ghost stories, candlelit pubs with frothy mugs of ale and live blues, you really work up an appetite. And what is better than late-night tacos? The Taco Shop on St. George Street has got you covered. The hip, surf shack taco dive is quick with no frills, just great eats. Excellent Baja style tacos and burritos; the fish taco is awesome. Open till 2 a.m.

114 St. George St., between Hypolita and Treasury streets




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January 2017