One of the Coolest Cities You’ve Never Been To: St. Augustine, Florida

No, you haven’t walked out of a time machine—you’ve just stepped foot in St. Augustine, Florida, where the town’s history dates back to 1565. Here, cobblestone streets and the remnants of fortress walls look out across a vivid view of blue-green water. Horse-drawn carriages and a life-size replica pirate ship only add to the imagery.

Even if the pirate ship isn’t real, the history is: St. Augustine is the U.S.’s oldest continually occupied European settlement. “St. Augustine is my favorite city in the world,” says Kevin Ip, who moved here to attend Flagler College and fell in love with the city. “I love how green everything is and how every street has such character.” To help you make the most of 24 hours in this historic coastal city, Ip shares his favorite St. Augustine attractions.

Take a stroll along the sea wall

Construction on the St. Augustine sea wall began in 1696. Today, it protects against rough waters and is the perfect place for a romantic stroll.

With a population of about 14,000, St. Augustine is relatively small. But it’s packed with must-see destinations you can hit on a leisurely stroll. “I think one of my favorite qualities of St. Augustine is how close everything feels,” says Ip.

Start at the Bridge of Lions along the sea wall that overlooks the scenic Matanzas River. Originally built in the 1600s, the sea wall now serves the dual purpose of protecting the city from Florida’s infamous hurricanes and providing its residents a sunny spot to congregate and relax. “On Cathedral Place, right by the Bridge of Lions, there’s a coffee shop called the Kookaburra that’s absolutely phenomenal,” Ip says. Grab an Australian-style “flat white” to sip as you walk, or just relax on one of the many benches lining the waterfront.

Explore the grounds of a 17th-century fort

Located on the shore of Matanzas Bay, Castillo de San Marcos is the oldest masonry fort in the continental U.S.

From the Bridge of Lions, a 10-minute walk down the sea wall will lead you to Castillo de San Marcos, an old masonry fort that’s been preserved as a museum. Constructed by the Spanish in the late 1600s, the fort was originally built to defend Florida and the Atlantic trade route. Even if you choose not to go inside the fort, a walk around its grounds shows the influence of Spanish, Native American and English cultures—and gives you a sense of the incredible amount of time and effort that went into keeping St. Augustine safe over the centuries.

Indulge in some retail therapy

From the Castillo de San Marcos, walk about 10 minutes south to St. George Street, the center of downtown St. Augustine. This pedestrian-only thoroughfare is lined with boutiques, antique shops, restaurants and galleries—the majority of them locally owned. A block off of St. George, you’ll find The Golden Gypsy, which specializes in internationally sourced art, jewelry and home decor. Or treat yourself to a hand-rolled cigar from JC the Cuban Roller. (Owner Julio Cordero started the business in 2007 but has been hand-rolling cigars for more than 20 years.) If you’re in the mood for a savory snack, Olde Town Jerky serves exotic treats ranging from alligator to python and snapping turtle. And for your sweet tooth, stop by the St. Augustine institution Whetsone Chocolates, which has been making fudge, caramels and other sweet treats since the 1960s.

Don’t forget the beach!

Spend a day relaxing in the warm waters of St. Augustine Beach.

You can’t visit Florida without wiggling your toes in the sand. Across the Bridge of Lions, St. Augustine Beach boasts pristine, white sands and sparkling, clear water. Less well known is Kevin’s favorite, Vilano Beach, located just north of downtown’s historic district. Vilano has a strong current that makes it the perfect spot to hang 10. For the best waves, take your board over to the pier near the beach access.

Dine al fresco

End an evening in St. Augustine by catching the sunset while you dine al fresco.

Cap your day in St. Augustine with a sunset meal. “The restaurant scene is pretty eclectic, and there’s something for everyone,” Ip says. He recommends snagging a seat on the patio of A1A Ale Works, a local taproom and restaurant overlooking the bay. Order from their list of specialties—Ip’s favorite is the Mango BBQ Chicken, which he pairs with one of the many local beers on draft. For a pricier but equally delicious option, head just north of the city to Cap’s on the Water, where you’ll find fresh seafood and a front-row seat to picture-perfect sunsets. A bucket of you-shuck-’em steamed oysters and, of course, a Key lime dessert, is the perfect end to your Florida adventure.

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