Miami and Orlando may get most of the attention when it comes to vacationing in the Sunshine State, but if you’re looking for a hidden gem that offers the same level of eclectic music offerings, imaginative culinary creations and satisfying entertainment venues, with a less touristy feel…Jacksonville is your diamond in the swamp.
I moved to Miami from Denver for a job, and while the city was certainly exciting—with its infinite influx of party-crazed tourists—the charm quickly wore off. I soon found myself stagnating at home, binge-watching foreign drama series and nature documentaries.
Enter my co-worker Olivia, a bubbly Jax native with an unquenchable zest for life and unshakable loyalty to the Florida Gators. She invited me to tag along for a weekend trip to her hometown, assuring me that I’d love it.
When Olivia has her mind set to something, you’d better go along or be prepared for battle. The next Friday, I found myself in the passenger seat of her Jetta, speeding up I-95 toward Jax.
The Jacksonville cityscape has a unique appeal. The broad, mirrored face of the Wells Fargo building dominates the skyline, which looks especially surreal on a cloudy day when it gives the illusion that you can see right through it. Another unmistakable feature is Jacksonville’s Main Street Bridge, whose twin towers stand like a pair of blue sentinels over the smooth waters of the St. Johns River, bisecting the downtown area and separating the main historic core from its Southbank. Lit brilliant blue at night, the bridge transforms into a glowing beacon against the skyline.
We arrived in Jacksonville around noon and stopped in the city’s trendy San Marco neighborhood, which, along with other Jacksonville neighborhoods like Brooklyn and Five Points, had undergone a transformation in recent years—a “trendy-fication” if you will. Driven by the millennial generation’s predilection for blending the vintage with the modern, San Marco’s historic commercial district is dotted with indie boutiques, craft breweries, imaginative cocktail bars and creative eateries.
Because Jacksonville channels more of a Southern vibe than her sister cities, we thought it only fitting to cap our five-hour journey north with some comfort food at the Maple Street Biscuit Company, whose delightfully creative treatments push that lowly baked good into the realm of gourmet cuisine. How else would you describe The Squawking Goat sandwich, with its all-natural fried chicken strips, goat cheese medallions and homemade pepper jelly?
After fueling up, we began the weekend’s excursions with a tour through a couple of Olivia’s favorite art galleries before they closed for the weekend. She explained that Jacksonville takes pride in cultivating its creative vibe, and is quickly becoming known for its thriving art scene. In fact, if you happen to be visit around the beginning of the month, the city’s self-guided First Wednesday Art Walk is a must-see, with monthly themes, music and guest artists—all of which keep it fresh even for the locals. It’s hard to miss the art scene in Jax—one can find a plethora of art events and excursions to fill every day of the month.
The Museum of Contemporary Art (MOCA) is a Jacksonville staple, but downtown Jax also features a number of smaller art galleries. Our first stop was the Southlight Gallery, which is a far cry from the sterile, highbrow spaces one might normally associate with galleries. A collaborative art gallery, Southlight is more a cooperative, community space, showcasing local artists and hosting events, workshops and lectures. In a similar vein, The Space Gallery also defies the traditional gallery form, presenting an inviting, creative atmosphere, with its contemporary installations beautifully presented against a backdrop of gritty, exposed brick.
As evening fell, we made our way to the Super Food and Brew, a health-conscious gastropub that Olivia had been a loyal customer of since its days as a humble food truck. Its wonderfully varied and reasonably priced menu did not disappoint, particularly the blackened fish sandwich with a side of crunchy, seasoned yucca fries, washed down with a locally brewed stout on tap.
We didn’t have to walk far to encounter one of Jacksonville’s crown jewels: the historic Florida Theater. Built in the 1920s, the cavernous interior—complete with decorative columns and moldings and red velvet curtain—harkens to pre-Depression-era glamour. I was immediately in love.
Over its nearly 100-year history, the theater has featured tens of thousands of movies and shows. Elvis Presley even performed there…twice! A steady decline in the 1970s prompted its sale and subsequent rebirth as a cultural and civic center, and it now hosts an eclectic array of events nearly every night of the week, from classical concert productions and modern dance performances, to internationally renowned rock bands, magicians and even laser light shows. Olivia had managed to snag us a couple of tickets to a stand-up show, where we and nearly 2,000 others filled the space with tear-jerking laughter.
The night was still young when the show ended. As we were already in the heart of The Elbow—the booming L-shaped downtown entertainment district, chock-full of restaurants and bars—we had plenty of after-hours options to choose from. We ended up at Dos Gatos, a dimly lit, speakeasy-esque cocktail bar with a cheeky sense of humor. Deliciously lubricated by a couple of sweetly spicy orange jalapeño margaritas, Olivia and I danced unapologetically in the crowded space, rocking out to a fun mix handspun by the live DJ.
Having spent that night at Olivia’s parents’ home in the bohemian Five Points neighborhood, the next morning we brunched just a short walk away on King’s Street at Goozlepipe & Guttyworks, which, with its steampunk-style multi-level dining space, certainly lived up to its wacky name.
Then we headed back downtown for a self-guided tour of the city’s famed street art. From clever, thought-provoking murals encompassing an entire building wall to beautiful abstract mosaics wrapped around concrete columns and archways, splashes of color melded seamlessly with the surrounding brick and asphalt. Surely that was the intention nearly 20 years ago when the Cultural Council of Greater Jacksonville designated an entire program to promoting art in public places.
After building an appetite walking around downtown, we stopped in at Bellwether for a late lunch. Specializing in elevated Southern classics, Bellwether gave me a whole new perspective on Florida cuisine. I went for the Shrimp & “Grits,” served with johnny cakes, a house-made cornmeal flatbread, in lieu of the grits. Accompanied by house bacon, bread & butter jalapeños, roasted corn, garlic cream, and house hot sauce, it was the most delicious plate of food I’d eaten in recent memory.
A quick trip back to Five Points to freshen up—and slap on a pair of heels—and we set off on our last adventure for the weekend: back to The Elbow and its Myth Nightclub. Myth combines the class of a cocktail lounge with the high energy of a dance club. We allowed ourselves to be carried away by the strobing lights, heavy beats, strong well-crafted drinks and contagious excitement of the other club-goers well into the wee hours of the morning.
As we drove back south the next morning, I realized that my weekend in Jacksonville was the first weekend I had truly enjoyed since my move to Florida. Not even my wicked hangover could keep me from smiling.