14 Reasons to Drive to St. Augustine

Anyone who’s lazily flipped through the frayed Trivial Pursuit cards at their local dive bar knows the oldest city in the United States is St. Augustine, Florida. And while it may seem odd that a state best known for sprawling condos and strip mall valhalla would also be home to some serious history, St. Augustine is teeming with the stuff. Whether you’re into old architecture, museums, forts, or haunted bars, you’ll find it within a few blocks here. And beyond that, there’s plenty of other reasons to make the five-ish hour jaunt up I-95. 

Old Town St. Augustine is full of the same Old Florida architecture that draws people to Key West, which you’ll find wandering its narrow streets. Aviles Street is the granddaddy of them all, the oldest street in America and the heart of the city’s arts district. In addition to hosting studios and galleries, it’s also where you’ll find the Ximinez-Fatio and Father O’Reilly House Museums.
Meandering through the Old City will also bring you past the Oldest Drug Store, a fascinating look at how people got medicine before there was a Walgreens on every corner. History buffs can revel in the Oldest House Museum, the Government House, as well as the Old City’s impressive collection of centuries-old churches and basilicas.

Are ghost tours a little cheesy? Yes, of course they are. But so is every Hallmark movie ever created and that doesn’t stop people from binging them every Christmas. And since you’re in one of America’s most haunted cities, meeting its most notorious dead residents seems only appropriate. Any number of ghost tours will take you ghost hunting around the Old City, making stops at some sites that are both historic and haunted.

One regular stop is the Oldest Wooden Schoolhouse, an 18th-century classroom where ghosts of children wreak havoc with divining rods. Also try to score a night tour at the Old Jail, constructed in 1891 by railroad magnate Henry Flagler and home to spirits of hardened criminals. The Huguenot Cemetery right near the city gate is filled with victims of yellow fever, most famously a judge who still roams around. The city’s iconic lighthouse is also reportedly haunted by three children who died playing on a rail car while it was under construction in 1873. Even Flagler College is said to house the spirit of one of Henry Flagler’s mistresses, a mysterious “woman in black” who was kept there during its days as the Ponce de Leon hotel.

Walking through haunted buildings and cemeteries is cool and all, but they’re exponentially more fun when tequila shots are involved. St. Augustine has almost as many dead bar regulars as it does live ones, the most famous of which is a guy named George who still frequents Scarlett O’Hara’s. The bar’s original occupant built the house out of unrequited love, and still smashes glasses to the ground, pushes stuff around the bar, and plays the jukebox when he’s in the mood.
In addition to one of America’s most haunted bars, you can also drink with the dead at Stogies Jazz Club. As the story goes, when the original building on this site burned down, four degenerate gamblers in the upstairs parlor refused to leave their poker game and died. They still play upstairs, and have been known to play tricks on visitors who frequent the upstairs bathrooms.

St. Augustine proper is seriously lacking in the surf and sand department, but fortunately, the city of St. Augustine Beach on dreamy Anastasia Island is just a 15 minute ride away. In addition to multiple miles of soft sandy shore, the area is also jam-packed with bars and restaurants, making it the perfect spot for beachy bar hopping. Swing by the long-standing Sunset Grille to load up on Coconut Shrimp or grab some classic Yucatán cuisine at Playa Chac-Mool.

For true beachside isolation, take the 15 minute drive to Guana River Preserve, allegedly the spot where Ponce de Leon first laid eyes on Florida and a beach unlike any in the state. Rich, golden sands sit at the base of towering grass-covered sand dunes, giving the impression you’re somewhere closer to the coast of Africa than you are in Florida. It’s rarely crowded, and is also a good spot to hunt for shark teeth if you’re looking for some free souvenirs.

People have been calling the Floridian peninsula home for roughly 10,000 years, but compared to their scalier neighbors, those are some serious rookie numbers. The ancestors of America’s modern-day alligators have been hanging around the region for tens of millions of years, and there’s no better place to get acquainted with the slithery beasts than the St. Augustine Alligator Farm Zoological Park.

Founded back in 1893, this historic park is one of the oldest surviving attractions found within the Sunshine State, and is currently the only zoological park on earth that houses all 24 crocodilian species. Not content to walk around and look at these beasts from ground level? The farm offers a full ropes course complete with ziplines, where you can speed over top of their peering eyes and snapping jaws, ever grateful for the harness keeping you in the treetops.

If you’re searching for ultra-plush accommodations just steps from the city’s downtown core, few locations compare to the Casa Monica Resort & Spa. This storied retreat made its grand debut in the heart of St. Augustine back in 1888, adorned with an ornate Moroccan architectural flair and a sumptuous Mediterranean-themed restaurant, to boot.

For a spot with a little more character, book a night or two at The Local. The retro-Florida motor inn sits on beachy Anastasia island, done up in tropical wallpaper and plenty of pastel pinks. It feels like the Florida vacation accommodations of childhood road-trip memories, updated with high tech features like digital keys, flat screen TVs, and USB ports. It also gets you access to its fleet of bicycles, so you can explore the city without a car.

It is widely known that St. Augustine was the first city in what is now the United States. But the area is also home to the first legally-sanctioned free Black Settled in the country, Fort Mose, established in 1738. Founded by escaped British slaves who gained freedom by converting to Catholicism and helping the Spanish defend their territory, the fort served as the northern defense post for the Spanish during the War of Jenkins’ Ear. The National Historic Landmark is also recognized as one of the original sites on the southern route of the Underground Railroad.

The oldest city was also an important place for politics and progress during the Civil Rights era—Dr. Martin Luther King Jr. was arrested here during a protest. Learn about the dark and sobering history of local Civil Rights leaders’ fight and contributions to equality at ACCORD Civil Rights Museum (by appointment only), the Constitution Plaza, and Lincolnville Museum & Cultural Center.

Plastic surgery can certainly work wonders on crow’s feet and chronically-thinning lips, but for true age-defying wonders, nothing compares to a dip in the fountain of youth—a fact that 15th-century explorer Juan Ponce de León knew all too well. Though he never did discover this mythical attraction during his 1513 visit to the Florida coast, his legacy lives on at the Fountain of Youth Archaeological Park, a 15-acre estate that offers visitors a deep dive into the history of St. Augustine and the surrounding area. And also affords a chance to take a drink from the land’s natural spring, which might not turn back time like a facelift but also costs a lot less (and doesn’t require surgery).

While the park is home to a wealth of reconstructed Spanish Empire-era structures like the Nombre de Dios Mission and Chalupa Boathouse, there’s also a wealth of information available about the region’s earliest inhabitants, the Timucua. This indigenous population once laid claim to a vast expanse of land stretching from modern-day central Florida to coastal Georgia, but widespread colonist-borne disease, violence, and warfare ultimately spelled doom for the Timucua community throughout North America. Visitors can catch a tiny glimpse of the area’s native heritage at the Timucuan Village anoti, a modern structure that emulates the dwellings once common across the region.

Just east of downtown St. Augustine, 16,000 acres of unspoiled Florida coastline await eager adventurers at Anastasia State Park. Officially established in 1949, this sprawling peninsular preserve has been a popular outdoor recreation spot for decades, offering ample opportunities for waterfront camping, ocean kayaking, and bronzing beneath the hot Florida sun.

Humans are a regular sight around Anastasia State Park, but the wilderness refuge has also earned acclaim thanks to its feathered inhabitants, with about 200 different avian species found across the park. While shorebirds like the least tern and black skimmer are frequent visitors, fortunate birders may be able to spot a roseate spoonbill or wood stork resting on the water. Don’t forget your binoculars.

It’s no secret that St. Augustine is home to a pretty killer food scene—after all, the city has had roughly 450 years to perfect the craft. Columbia’s had the longest to get it right, a 1905 Cuban/Spanish spot whose Tampa cousin is the oldest restaurant in the state. Also in the Old City you’ll find Casa Maya, where fresh Mexican seafood follows the city’s best fresh made guacamole. For more casual Mexican stuff, stop into Burrito Works Taco Shop, where you’ll get two meals’ worth of food for under $15.

Ice Plant Bar’s fine farm-to-table cuisine and spectacular cocktail menu has made it a locals’ go-to, and probably the most common rec you’ll get asking around the city. Catch 27 has all the Florida seafood classics, plus Minorcan Clam Chowder—a tomato-based stew introduced to the city centuries ago by Spanish laborers. BBQ lovers will delight in Mojo BBQ, where the sandwiches filled with smoked brisket and pulled chicken are a worthy reward for a day of hard-core walking.

Not content with simply being the oldest city in the Lower 48, St. Augustine is also home to the oldest masonry fort in the entire nation. Known as the Castillo de San Marcos, this massive structure was built in the tail end of the 1600s by the Spanish Empire to protect the surrounding village from attacks.

While the fortress did repel two British-led advances in the early 1700s, it also spent a brief stint under English ownership from 1763 to 1783, then returned to Spain before ultimately being bequeathed to the United States in 1821. For a thorough look into the history of this coquina stone formation, be sure to have the University of South Florida’s Virtual Tour on call as you stroll along the storied walls.

Florida’s boggy swampland may not seem particularly conducive to grape-growing, but life—and more specifically, modern agriculture—finds a way. Case in point? San Sebastian Winery, a downtown spot that’s been a local fixture since 1996.

There’s a treasure trove of wines to be opened here, including Pinot Grigio, Petite Sirah, and Cream Sherry, but for a truly idyllic experience, be sure to swing by on the weekend to take advantage of the Cellar Upstairs. Equipped with live music and an open-air rooftop patio, it’s tough to find a more relaxing spot to waste the night away with a nuanced glass of Cab in hand.

Not feeling the whole downtown hustle and bustle? No worries—the Embassy Suites by Hilton St Augustine Beach Oceanfront Resort is here to provide you with the perfect shoreside escape. This serene retreat has mastered the art of coastal relaxation, offering a wealth of tropical cocktails served fresh from the lobby-based Rhum Bar just steps away from the sandy coastline.

It’s a little difficult to encounter pirates in modern-day Florida—unless, of course, you’re hanging around Magic Kingdom—but the St. Augustine Pirate & Treasure Museum does a pretty spectacular job of highlighting the peninsula's swashbucklers of yore.

There are more than 800 different artifacts showcased across the museum, with exhibits ranging from informative—the life and times of Blackbeard, a notorious pirate that terrorized the eastern North American coast and ultimately lost his life during a battle on North Carolina’s Outer Banks—to total fantasy, including memorabilia from filming of Disney’s Pirates of the Caribbean.

Florida’s craft beer scene has undergone major growth over the past decade, and the Sunshine State’s oldest city is no exception. Though Florida isn’t particularly known for being pedestrian-friendly, St. Augustine’s top beer destinations are clustered around the city’s colonial core, making it particularly conducive to car-free boozing.

To kick off the festivities, head just west of the San Sebastian River to Bog Brewing Company, a small brick-clad venue offering a wealth of beers ranging from the hop-laden Spiral Jetty Hazy IPA to the Smoked Datil Ale, a brew crafted using native St. Augustine peppers. After a couple of drinks, head east for a Foolish Fire pumpkin ale at Dog Rose Brewing Co., a Ponce’s Pale Ale at Ancient City, or drop into all three spots to complete a lauded St. Johns County hat trick (hey, it’s a thing).

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