Jacksonville’s downtown is one of our favorite familiar scenes, with good reason. Before moving to South Florida, we spent a few years living in Jacksonville and found it to be one of the most underrated cities in the U.S. From the bars along Bay Street to the Brooklyn area’s new nuances, there is something for everyone. A far cry from the over-saturated Town Center or beach areas, downtown Jacksonville is a slow beat, a riverside walk and a cold beer on a Saturday all in one.

Riverside’s Chill Side

A great way to get familiar with the city is to start out in historic Riverside where you can peruse kitschy and endearing antique shops, as well as locally owned boutiques and bars that draw in the colorful downtown scene with a vengeance.  The friendly nature of this area of downtown Jacksonville makes for a great weekend excursion as well as an exciting night on the town.

Strolling in downtown Jacksonville

For one of the best brunch restaurants in Jacksonville (or dinner, for that matter), check out Derby on Park, a contemporary American restaurant that is located in a refurbished building in Riverside – the site of the old diner that use to inhabit the space. Their back patio area is perfect for enjoying the Jacksonville weather almost any time of year, and the space itself is a Jacksonville cultural landmark. This area, formally known as the Five Points area, contains not only Derby on Park but in fact several popular eateries within mere feet of one another. Another of our favorites in the middle of Five Points is Black Sheep Restaurant, a slightly more upscale contemporary American outfit with a beautiful rooftop patio that is perfect for enjoying a glass of wine with lunch, or joining a group of friends for an unwound brunch. Their rich and tasty menu never disappoints, and includes everything from contemporary American classics to spins on Southwestern Asian dishes such as the Banh Mi Sandwich.

After brunch or dinner, Five Points offers numerous spots for a casual night cap. A spot we’ve frequented would be Raindogs or Birdie’s Bar, both just steps away from the main roundabout and again within a few dozen yards from the front door at Derby on Park. Birdie’s is known for it’s laid back attitude, interesting internal decor that features punk-inspired paraphernalia, inexpensive drinks and a jovial atmosphere with a lot of regulars who are eager to strike up a conversation! Raindogs is also a laid back, chill bar to have a drink and peruse the amazing local visual artists who display their work on the walls there.  On certain nights you’ll get to sit back with a beer while live music entertains you as well. (Try their white sangria for a real treat!) Both locations can range from the casual and relaxed to the outright raucous, depending on the time of day or night.

If you’re interested in vintage movie theaters and cinema, you have to check out the also locally-owned Sun-Ray Cinema, a virtual time capsule from the glory days of 1960’s movie houses. They offer rotating classics like Casablanca, to modern titles, but their biggest draw is the amazing independent films that are screened here. The scene inside is fantastically retro, down to the large-stand gaming machines that adorn the inside corridor. Grab a ticket, a beer, and some popcorn, and find yourself back in time no matter which movie they’re showing!

The legendary Sun-Ray

During the daytime, make sure to find your way to scenic Memorial Park (locally known as Riverside Park), a beautiful (and aptly named) river-facing grassy plateau where you can bring your coffee or lunch and sit in the shade by the St John’s River while the city walks by.  You can also take a jog around the park’s pathway or get in on a game of soccer or frisbee in the center of the expansive, well-maintained field.

The Brooklyn Beat

New to Downtown Jacksonville is the Brooklyn scene, right across from the St Johns River and nestled in between the nightlife and the vibe of Riverside. One of the additions to this part of the city is the well-known Burrito Gallery restaurant, with it’s original location in the heart of the city on Adams Street in downtown Jacksonville.

Named for it’s idea of focusing on local artists and featuring impressive paintings on it’s walls, this particular eatery was a favorite of ours. In Brooklyn, it’s now a fun and family-friendly place to get great local food with a view from the second floor that overlooks the river.

The draw of the Brooklyn area of Jacksonville is enhanced by the modern architecture that encircles the eateries, a vibrant and colorful palate of buildings that seem to stand alone in the district. Though close to both the bustling downtown and the hipster-esque lifestyle of Riverside, Brooklyn lives in a largely business area, welcoming everyone from late night party goers to families and briefcase holders. If you’re looking for things to do in Jacksonville, check out the walk across the street and enjoy the river view, you might even see a few dolphins swimming past as you stroll!

Downtown Nightlife

At night, head over to the real downtown, just minutes away from Riverside. Downtown you’ll find a mix of bars and nightclubs of all varieties to entertain you with music and excellent bartenders, ready to mix up your favorite cocktail or let you enjoy one of their signatures. For a fun and very classic Jacksonville experience, head over to Dos Gatos, directly across from the famous Florida Theater and the best bar in Jacksonville.  Owners Jay and Joy Albertelli are excellent hosts and have made this bar a local favorite for years. Try their delicious “Stolen Fish” cocktail, and tell them Tracy and Justin sent you!

For a more musical scene with live bands and a great crowd, head over a block to 1904 Music Hall. This bar offers a wide range of beers from local brews to international, depending on your taste! Check out the back patio area where local graffiti artists rotate their work, it’s a great place to sip a brew with friends and chat.

Downtown Art-life

For even more of the amazing art scene, Jacksonville has the MOCA, a modern art museum with an entryway that leads you to an expansive area where the walls are hand-painted by different artists before every opening event. Hosting some of the best modern art pieces from around the world, it’s sure to expand your mind! The museum’s restaurant, Café Nola, is also exceptional. Make sure to ask for their butter-of-the-day to spread on their sweet and delicious bread. (My favorite was lemongrass.)

Across from the MOCA sits Hemming Park, where every first Wednesday of the month the area hosts an expansive and impressive Art Walk. Everything from handmade jewelry, to local art, to performance art are on display for the evening.  Walk around and peruse the scene with a cold local beer, which many vendors have for sale around the festivities. While you’re there, make sure to step into Chamblin’s Book Store, our favorite local shop selling books of any age and genre, with genial and knowledgeable owners and a cozy coffee shop offering warm drinks, bottled beer, and vegan or vegetarian wraps and soups. We love this place, and it gets credit for about half of the books that remain in our library!

More Than Just a Beach Town

While coastal, Jacksonville is much more than just a beach area if you venture into the heart of the city. The art museums and general culture are a fresh window Take a walk along the St. Johns, sip a local brew and enjoy the local scenes, rife with art and culture. There are many hotel options in this area, many with views of the river. Check out the Hyatt, the Omni, or the Doubletree for optimum access to the city center.  Settle in to the artsy and upbeat scene of downtown Jacksonville, make a few new friends, and sample the local eats. You’ll be glad you did!