St. Augustine, the Old City

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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Bridging the Gap

Hop on the Bridge of Lions and head over the Matanzas Bay (Massacres Bay) to Anastasia Island, location of two must-see tourist spots and home to some of the best surf breaks in Florida.

   St. Augustine Lighthouse & MuseumPanoramic Views As the nation’s oldest port, St. Augustine is steeped in the maritime tradition. So the need for a solid lighthouse was imperative in the days before satellite tracking, GPS coordinates and radio signals relaying warnings of stormy weather. The St. Augustine Lighthouse answered the call in 1874, built in the same location as the Spanish watchtower dating back to the late 16th century, which was Florida’s first lighthouse (named such in 1824—Florida was ceded to the U.S. in 1819).

   Now the St. Augustine Lighthouse & Museum is open to the public and visitors can trek up all 219 steps to the lantern room. Along the way visitors can lift barrels simulating the weight of the oil needed to light the lamp for the 1st-order Fresnel Lens, which comprised of 370 hand-cut glass prisms arranged in a beehive shape, measuring 12 feet tall and six feet in diameter. Step outside and peer across the bay for a panoramic view of the city. 81 Lighthouse Ave., 904-829-0745,



Crocodile at the St. Augustine Alligator Farm   Cowabunga  The newest attraction at one of Florida’s oldest zoological parks, the St. Augustine Alligator Farm, may be the most exhilarating to hit the city in years. The Alligator Farm has long been known as the place to see crocodilians. Founded in 1893 by George Reddington and Felix Fire, the St. Augustine Alligator Farm’s Land of Crocodiles is home to all 23 species of the worlds’ crocodilians. But now visitors can get a completely different perspective of the largest reptiles on the planet.

 Crocodile Crossing - St. Augustine Alligator Farm  The newly christened Crocodile Crossing takes brave visitors up into the trees and zips them across the park on steel-cable zip lines. Among the 10 zip lines, as tall as 50 feet high and 300 feet long, there are swinging log bridges, rope bridges and ladders, even a gliding board that surfs passengers from one platform to another. The course takes between an hour to an hour and a half to complete and is completely worth the price ($65 for the complete course) to get a bird's-eye-view of a day in the life of a crocodile. 999 Anastasia Blvd., 904-824-3337,



San Sebastian Winery - reds and portsSideways, Florida Style

Widely known for orange juice, few people know that Florida produces some pretty palatable wine. One of the most prestigious wineries in Florida, the San Sebastian Winery, located along King Street, just west of St. George Street, in, you guessed it, a Flagler building, welcomes more than 100,000 visitors each year to the winery and extensive tasting room.

   Founded in 1996, San Sebastian is the second largest winery in Florida (sister winery to Lakeridge Winery & Vineyards), and utilizes the local muscadine grape and other local bunch hybrid grapes suited for Florida’s harsh clime to produce eight premium table wines (2 red, 6 white), two dessert wines and a sparkling wine. The recipient of over 350 awards, San Sebastian wines have become a fan favorite not just in the state but also abroad, a common souvenir tucked into the checked baggage on outgoing flights. San Sebastian Winery - whitesThe Castillo Red and the Port are rich and complex in flavor and aroma, while the Reserva is a fine example of depth the Florida grape can yield.

   Daily winery tours and wine tastings at San Sebastian are complimentary (no reservations necessary, running time: about 45 minutes), and the gourmet gift shop is a must stop for any oenophile. The popular The Cellar Upstairs wine, jazz and blues bar is open weekends and is a great way to enjoy the fruits of San Sebastian’s labors. 175 King St., 888-352-9463,



Contentions ran high as warring European nations vied for footholds in the newly discovered and resource-rich New World during the colonial era.  St. Augustine was no exception, a point dispute ever since it was founded in 1565, leading to the construction of two colonial forts that still stand today.

  Castillo de San Marcos Situated on the St. John's River and the Matanzas Bay, the bastion-style Castillo de San Marcos construction began in 1672 and was completed in 1695. Only one of two forts in the world made of coquina (the other being Castillo’s sister fort to the south, Fort Matanzas), it had a decided advantage against cannons and projectiles, absorbing the shot versus deflecting. As the United States' oldest masonry fort, and touting the moniker of unconquerable, Castillo de San Marcos weathered British sieges, the occupation of the Spanish, British and the U.S., and the test of time, now sitting as a historical landmark and the most recognizable attraction on St. Augustine. Open to the public seven days a week.

 Fort Matanzas On Rattlesnake Island 15 miles to the south of Castillo de San Marcos, sits Fort Matanzas holding guard of the Matanzas Inlet at the mouth of the Matanzas River. The location of the French massacre in 1565 led by Spanish General Pedro Menéndez de Aziles (giving the fort/river/inlet/etc. their names), construction of the fort began in 1740 in response to the 39-day siege of St. Augustine engineered by Georgia Governor James Oglethorpe. Fort Matanzas, in collusion with Castillo de Sans Marcos, gave St. Augustine safe harbor throughout the remainder of the Colonial Era. Open to the public seven days a week.


Saint George Street - St. AugustineSaint George Street

Once one of the city’s main thoroughfares, where colonists and settlers hocked their wares, pirates and privateers imbibed rum and ale, and raiding parties burned to the ground while beating hasty retreats, Saint George Street is now a tourist destination even Disney could be proud of. Now the heart of the city’s historic downtown area, museums and historic attractions, galleries, restaurants and storefronts line the street, each beckoning promenaders to explore and find that perfect souvenir.

Colonial Spanish Quarter Museum - St. Augustine   Take a trip back to 18th-century St. Augustine in the Colonial Spanish Quarter Museum. A self-guided tour through the garrison town gives visitors a glimpse into the everyday at the Spanish outpost during the 1740s. As a living history museum, historical interpreters dressed in period costume man a blacksmith’s workshop and a leather craftsman workstation, carry out the daily activities of a soldier’s wife, and scribe using quill and parchment. The two-acre museum is open daily, 9 a.m.-4:45 p.m., 904-825-6830


Night Cap

After a heavy day of touring historic haunts, shopping and cultural hotspots, an evening of barhopping is in order. Following the ghost tours, continue the good times at these night spots.

  • Taberno del Gallo - St. AugustineColonial Libations  Tucked away in the Colonial Spanish Quarter on St. George Street is a true throwback. Established in 1734, Taberna del Gallo is unassuming tavern with a small sign sitting above the door, but a great place to take a break from touring St. George Street and enjoy a drink. The small, dark tavern (candle/torch lit—keeping with the Spanish Quarter's historical integrity), where the barman is dressed in period garb, is a one-of-a-kind watering hole with a small, rustic courtyard and a few shadowed snuggeries where tourists can enjoy a small yet diverse and tasty beer selection, a few choice Spanish wines and a sangria, which is a house specialty. Open 12-7 p.m., Sunday through Thursday; 12-11:30 p.m. Friday and Saturday. 35 St. George Street


  • Rhett's Piano Bar & Brasserie - St. AugustineGone with the Wind  Scarlett O’Hara’s Pub & Restaurant and Rhett’s Piano Bar & Brasserie along Hypolita Street are two popular haunts for locals and tourists alike. Scarlett’s, housed in a 1879 house (another historic building—go figure), has three areas to enjoy a drink and food: the main inside bar, the outside oyster bar with live entertainment, and the upstairs Ghost Bar, said to be haunted by the original builder of the house. Come as you are; there is no need for a reservation. 70 Hypolita St., 904-824-6535,  
  • Rhett's Piano Bar & Brasserie   Rhett’s Piano Bar & Brasserie, Scarlett’s neighbor (and third husband), is more of an upscale, modern piano bar, where specialty cocktails and martinis reign (try the Rhett Butler, a mix of Jack Daniels, cranberry juice, and lemon and lime). The food is phenomenal at Rhett’s. The small plates are perfect for a light bite, but if you’re looking for an entrée, we suggest the Organic Herb Crusted Grouper or the Maine Lobster Stuffed Chicken Roulade—out of this world. And the music at Rhett’s is first class, led by music director and house Pianist Samuel Clein. Dress is casual chic and reservations are recommended. 66 Hypolita St., 904-825-0502,


  • A1A Ale WorksCraft Brewed  Enjoy more than just good times at the A1A Ale Works. The brewpub overlooking the Bridge of Lions is the perfect place to while away the time on a lazy afternoon. With a knack for fresh seafood, A1A’s true specialty lies in its beer. Multiple winners at both the World Beer Cup and the Great American Beer Festival, A1A Ale’s taps are always flowing with their five standards: King Street Light Lager, Porpoise Point IPA, Bridge of Lions Brown Ale, Red Brick Ale, A.Strange Stout, as well as dabbling in specialties and seasonals (an amber Maibock was on tap while I visited; quite tasty). 1 King St., 904-829-2977,


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