Why the sprawling city of Jacksonville, Florida, is a great spot for a weekend getaway

Three historic neighborhoods in particular have tempted travelers for more than a century

Photo courtesy of Visit Jacksonville

Although it’s the largest city by area in the continental United States (840 square miles), Jacksonville manages to feel small. Venture beyond the urban core, and you’ll discover a patchwork of historic neighborhoods. Three stand out: Riverside Avondale, Atlantic Beach, and San Marco. Each came into its own around the early twentieth century, the results of Florida’s land and tourism booms. (In those days, Jacksonville was called the “Winter City in the Summer Land” because of the attention it drew from Northerners seeking warmer climes.) Together, these storied neighborhoods continue to welcome visitors with award-winning dining, jaw-dropping architectural variety, and, of course, the sunny beaches that appealed to travelers more than a century ago.

Leon Cheek residence

Photo from Alamy

Riverside Avondale

After the Civil War, Jacksonville emerged as a winter hub for Northerners living along the Eastern Seaboard. Wealthy families built elaborate mansions along Riverside Avenue, so named for its proximity to the St. Johns River. The Riverside neighborhood soon welcomed another wave of newcomers as a result of the Great Fire of 1901, which destroyed almost all downtown residences and businesses and remains the largest urban fire recorded in the South. Many affluent city dwellers moved a mile from downtown to the prestigious neighborhood. By 1910, Riverside Avenue was known as one of America’s most beautiful streets, and today, the neighborhood that grew up around it is home to the state’s most diverse assortment of architectural styles, including Prairie and a slew of Revivals—Gothic, Greek, Tudor, and Mediterranean, to name a few.

During the land boom of the 1920s, just south of Riverside, the Avondale neighborhood was born. It soon became another fashionable enclave for the well-to-do. Over time, the sister neighborhoods grew together and are now often considered as one.

The best way to get a feel for Riverside Avondale’s history is on a self-guided walking or driving tour of its stately mansions. (Check out Visit Jacksonville’s website for maps and descriptions of each notable spot.) Look out for the castle-like, Jacobethan Revival–style former home of Leon Cheek, who founded what later became the Maxwell House Coffee Company. And don’t miss Riverside Avenue’s collection of Prairie-style homes designed by Frank Lloyd Wright protégé Henry John Klutho; the street has more Prairie-style residences than any other outside the Midwest.

Cummer Museum of Art

Photo courtesy of Visit Jacksonville

The neighborhood is also home to the Cummer Museum of Art and Gardens, which features more than 5,000 works, including a highly regarded collection of eighteenth-century porcelain. Three themed gardens—English, Italian, and Olmsted—can be found behind the museum, each a work of art in its own right. Impeccably trimmed hedges and rows of bright blossoms line walkways that lead to fountains, reflecting pools, and sculptures—all with riverfront views.

Riverside Avondale is also home to the artsy and eclectic subdistrict of Five Points. One can easily spend hours wandering its massive vintage shops, such as Fans & Stoves and Five Points Vintage, hunting for deals on everything from vinyl records to antique medical equipment. Getting hangry? Mixed Fillings, a pie “speakeasy” that operates out of a hidden Dutch door behind an unassuming shop, will fix that. Just pick your pie—or opt for a pie flight—and dig in at one of the patio tables alongside the building. For a sit-down meal, head to trendy seafood restaurant River and Post. Ask for a rooftop table; although the upstairs menu is limited to appetizers and a handful of sushi rolls, you can sip the light and fruity Manifest Destiny (made with Champagne, peach, lavender, lemon, and vodka from local distillery Manifest) and take in stellar views of the river and city skyline.

Beaches Town Center in Atlantic Beach

Photo courtesy of Visit Jacksonville

Atlantic Beach

Atlantic Beach, a half-hour drive from downtown, was a tiny coastal community before railroad titan Henry Morrison Flagler showed up. After purchasing and connecting several existing area railroads to his Florida East Coast Railway in 1899, Flagler constructed the massive Continental Hotel there in 1901. Twelve years later, he sold the land on which the hotel sat, as well as the surrounding area, to the Atlantic Beach Corporation, which began laying the groundwork for a planned town. Despite several setbacks, including years of bankruptcy during World War I, the town was incorporated in 1926 and has remained a vibrant beachside community ever since.

Though the Continental Hotel is long gone, many visitors now stay at the 193-room One Ocean Resort, located mere steps from the Atlantic. It’s a quick stroll from the resort to Beaches Town Center, a hip collection of restaurants and shops lining either side of Atlantic Boulevard (which also delineates Atlantic Beach and Neptune Beach). Start the day at Atlantic Beach’s Homespun Kitchen, where you can grab a breakfast wrap made with organic eggs and turkey bacon (or go vegan with tempeh) along with a coffee brewed with beans from local coffee roaster Bold Bean. (Try adding a shot of Homespun’s house-made cinnamon syrup.) In the evening, cross the street into Neptune Beach for happy-hour oysters and sangria at The Local. Be sure to stop in for a pint of beer and a game of pool at Pete’s Bar, an eighty-seven-year-old institution and the diviest of dives.

Atlantic Beach

Photo courtesy of Visit Jacksonville

If you’re in Atlantic Beach, you’re probably there for its beaches. Rent all manner of water-sports equipment at Jax Surf & Paddle. The company also offers private surfing, stand-up paddleboarding, and fitness classes for all ages and experience levels. More outdoor fun awaits at Tide Views Preserve, a peaceful park on the Intracoastal Waterway with 2,500 feet of walking paths, fishing areas, and picturesque views. Be on the lookout for the resident wildlife, including great blue herons and hundreds of tiny crabs.

San Marco Square

Photo courtesy of Visit Jacksonville

San Marco

Trains may have ushered in the beginning of Atlantic Beach, but for San Marco, it was a bridge—the St. John’s River Bridge, which was completed in 1921 during Florida’s land boom. The bridge linked the burgeoning peninsula neighborhood with downtown Jacksonville, allowing cars to drive easily back and forth over the river. Four years later, real estate tycoon Telfair Stockton began work on a Mediterranean-inspired development he named after Piazza San Marco in Venice, Italy, which he had visited on a trip to Europe. The Italian influence is evident in much of the residential architecture, which is primarily Mediterranean Revival (though, like Riverside Avondale, San Marco also claims an array of construction styles).

San Marco Square, the main business district, is the neighborhood’s crown jewel. A fountain in the middle of the square is adorned with bronze lions—the symbol of St. Mark, the neighborhood’s namesake. Within walking distance, find a host of restaurants, shops, and attractions. Don’t miss San Marco Books and More, a mainstay since 1972, which carries novels of all genres along with colorful, leather-bound copies of literary classics. Watch a movie at the art deco San Marco Theatre, built in 1938, or catch a live performance at Theatre Jacksonville, the oldest continuously operating community theater in Florida (opened in 1919).

San Marco Theatre

Photo courtesy of Visit Jacksonville

Half a mile from the square, Wick: A Candle Bar is also worth a stop. After browsing and smelling upwards of ninety fragrances—ranging from the typical vanilla bean and gardenia to “old books” and basmati rice—visitors are instructed to mix and match their favorite scented oils to craft a customized candle. While you’re waiting for your creation to solidify, take a short stroll to V Pizza for a slice of authentic Neapolitan pie.

Before bidding farewell to Jacksonville, toast the town with a craft cocktail at Grape & Grain Exchange, a trendy neighborhood-bar-meets-package-store, or at Rue St. Marc, a small, stylish French-American spot with an extensive cocktail program. Popular options among the fifty-plus handcrafted beverages include the fruity Dahlia Blossom (brandy, citrus, and sparkling rosé) and the Uncle Buck (a take on the Moscow Mule with whiskey and bourbon).

This article appears in the Spring/Summer 2021 issue of Southbound.