10 Reasons to Drive to St. Augustine, Florida

Travel back in time with a trip to America’s oldest city.

Castillo de San Marcos
Castillo de San Marcos | Sean Pavone/Shutterstock
Castillo de San Marcos | Sean Pavone/Shutterstock

If you had to equate each American city with a celebrity, St. Augustine, Florida is certainly the Betty White of the United States: culturally significant, intoxicatingly charming, and incredibly, almost impossibly, old. We’re talking “oldest continuously-inhabited city in the Lower 48” old—and it would be the oldest in the entire nation if it weren’t for stunningly-beautiful San Juan just across the sea.

St. Augustine may be positively ancient (by US standards at least, as any European, East Asian, or South Asian citizen will be quick to tell you), but thanks to its unwittingly exuberant and captivating vibe, this beachy vacation destination doesn't feel a day over 400. Here are 10 standout reasons to make the trip out to St. Augustine.

Fountain of Youth Archaeological Park
Fountain of Youth Archaeological Park | ifoodijourney/Shutterstock

Plastic surgery can certainly work wonders on crow’s feet and chronically-thin 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 (pun intended).

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. Though they’re long gone today, 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.

Anastasia State Park
Anastasia State Park | Christina Marie Saymansky/Shutterstock

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.

St. Augustine Alligator Farm Zoological Park
St. Augustine Alligator Farm Zoological Park

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. In addition to its famous reptiles, the farm is also home to a wide array of other more cuddly species, including red-ruffed lemurs, two-toed sloths, and pygmy marmosets. It’s a sight to see, and definitely one of the strangest spectacles in a state famous for offbeat entertainment venues.

St. Augustine Lighthouse at Anastasia Island
St. Augustine Lighthouse at Anastasia Island | RodClementPhotography/Shutterstock

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.

Sunset Grille
Sunset Grille

It’s irresponsible to drink on an empty stomach, so make sure to swing by the long-standing Sunset Grille to load up on Coconut Shrimp or grab some classic Yucatán cuisine at Playa Chac-Mool—or hit up both, if you’re feeling bold. Once good old 5 pm hits, there’s a world of options just a few steps from the water, ranging from free-flowing beer and Bloody Marys at the all-day breakfast joint Beachside Diner to the Beachcomber St. Augustine, a casual watering hole that traces its origins back to the 1940s and offers a wealth of tantalizing tropical cocktails to its modern-day clientele.

The Ice Plant
The Ice Plant

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. As with most coastal Floridian cities, seafood reigns supreme around here, with classics like Conch Fritters and Lobster Tail sharing table space with unique additions like Minorcan Clam Chowder, a tomato-based stew introduced to the city centuries ago by Spanish laborers.

No matter your vibe, St. Augustine’s dining landscape has you covered. On a first date? Ice Plant Bar’s fine farm-to-table cuisine and spectacular cocktail menu is certain to wow any potential partner. Just went through a harsh breakup? Drown your sorrows with a healthy serving of nachos at St. George Tavern. In the mood for some of that tasty Minorcan Chowder we’ve been talking about? Catch 27 has all the answers. Whether it's decadent Southern BBQ, ocean-fresh seafood, or spice-laden Latin cuisine, hunger springs eternal from the heart of downtown St. Augustine to the outer fringes of St. Johns County.

Castillo de San Marcos
Castillo de San Marcos | Sean Pavone/Shutterstock

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.

San Sebastian Winery
San Sebastian Winery

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.

Casa Monica Resort & Spa, Autograph Collection
Casa Monica Resort & Spa, Autograph Collection

St. Augustine may be well into its 450s, but this golden gal is far from derelict when it comes to hospitality. 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.

Embassy Suites by Hilton St. Augustine Beach Oceanfront Resort
Embassy Suites by Hilton St. Augustine Beach Oceanfront Resort

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.

Bog Brewing Company
Bog Brewing Company

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).

Scarlett O'Hara's
Scarlett O'Hara's

Feeling fearless after all that housebrewed liquid courage? Get your goosebumps up at Scarlett O’Hara’s, rumored to be one of the most haunted bars in America. The neighborhood tavern’s upstairs Ghost Bar is apparently still under the jurisdiction of George Colee, the woeful soul who originally built the house all the way back in 1878. Coasters crashing to the ground, displaced glasses, and ghastly apparitions following closely behind patrons are just a few pieces of ghoulish evidence reported by visitors and staff over the years. Party at your own risk.

Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.

Jared Ranahan is a contributor for Thrillist.