A Perfect 1 Day Itinerary in Jacksonville: Hitting Up The Best Food and Shops

Kevin and I just got back from visiting family in Jacksonville, Florida, for Thanksgiving. While it was our first time here, we had no idea it would be so large. Believe it or not, Jacksonville is the LARGEST city in the continental US, stretching more than 840 square miles. Who knew?

So keeping the urban sprawl in mind, we hit the road with a plan. And my sister and niece joined along as Kevin and I mapped out our favorite kinds of stops — coffee shops, little bakeries and of course, farmers markets! Full disclosure: I have a weakness for all three. In fact, I once walked head-on into a lamp post after getting distracted by the farmer’s market by my office (resulting in 22 stitches). Yes, clearly I have a problem…

We weren’t sure what to expect – but Jacksonville didn’t disappoint. Check out our top picks below and soon you’ll be plenty caffeinated and ready to shop late into the night. Just make sure you keep your eyes open for those unexpected lamp posts!

Stop #1: Southern Grounds

My sister told us about Southern Grounds, located just minutes from downtown Jacksonville. She knows ALL about our love for coffee shops and suggested we be sure to check it out. This is definitely our kind of spot — where we could spend hours getting work done (but in all likelihood, just surfing Amazon!). We loved the indoor and outdoor seating, too.

I ordered a cup of coffee (my first of many this day!) and 2 chocolate chip cookies to sample while we were waiting. Kevin and I shared them — so stop your judging! The shop is geared more as a community hub — open late into the night with a full menu with food as well as a list of wine. We’ll be making our way back here on future trips, I’m sure!

Stop #2: Riverside Arts Market

The Riverside Arts Market is hosted every Saturday from 10 a.m. – 3 p.m., rain or shine. And clearly, we love a good market! It features a variety of small  and local businesses — everything from original artwork, baked goods, spices and ready-to-eat food. It’s also located under the Fuller Warren Bridge, which gives some nice shade and protection from Florida’s notoriously unpredictable and crazy weather. Though, I’m not so sure how well it would hold up from those torrential downpours (like the one a few days earlier that flooded the roads and tested our nerves as we hydroplaned all over!).

There is also an amphitheater that seats over 300 people and hosts live music. It makes a great way to spend your Saturday morning for an hour or 2. Insider tip: be sure to check out the sign maker in the middle of the market. You’ll know you hit the right spot when you see the flames shooting from the pieces of wood that he’s branding by using the power of the sun! We were intrigued and frightened all at once (but if you stare, be sure to use the special glasses to protect the eyes!)

Stop #3: Five Points, Jacksonville’s Hipster Neighborhood

Riverside’s funky, trendy 5 Points is considered Jacksonville’s arts and commercial district. Built in the 1930’s as Jacksonville’s first shopping area outside of Downtown, it is making a comeback according to a few of the shop owners along this walkable strip. You’ll find an eclectic mix of restaurants, bars (like Rec Room with its 80’s throwback arcade games) and antique shops. We spent at least an hour checking out all the retro items at 5 Points Vintage, where I STRONGLY held back from buying a set of framed taxidermy butterflies or a creepy doll to give Kevin nightmares for the rest of his life.

Other great stops on this trip include the vintage Sun-Ray Cinema, which shows first-run movies along with classics. In addition to traditional movie snacks, they offer sandwiches, hummus and pizza with unusual toppings (um, kimchi and Sriracha sauce pizza anyone?). We didn’t check out a movie this trip, but next time!

If you’re hungry from all that shopping, we recommend grabbing some sandwiches at The Bread & Board. The concept is pretty straight-forward here: with a menu consisting of tasty sandwiches along with their signature “boards” topped with smoked meats, cheese and bread for sharing. The owners hail from Portland, Oregon (which explains the wooden board cutouts on the wall in the shape of both Florida and Oregon). Though, full disclosure, we all recognized Florida, but let’s just say SOME OF US need a refresh on our US geography!

Stop #4:  Bold Bean Coffee Roasters – Riverside

Just when we started to get low on the caffeine, no fear! After all the walking and eating, we hit the road to check out Bold Bean Coffee Roasters, located about 5 minutes away by car. The shop sources all its coffee beans from small-scale family farmers from around the world and is one of just a handful of certified organic roasters in Florida according to our cool coffee barista. They also carry mostly certified organic beans that are grown and produced without chemicals or fertilizers. But what was Kevin most excited about? Clearly, the cookies. I’m sure the baked goods are just as healthy as the coffee, right?

Stop #5: Sweet Theory Baking Company

Okay, you’re thinking, haven’t you had enough baked goods yet? Umm, no! Besides, this next stop is an all-vegan bakery (which as I always say, that means it’s probably healthy…just don’t show me the label!). This place could easily be at home in Los Angeles with its hipster vibe and vegan, cruelty-free baked goods. There was no doubt, that we’d be making a stop here along our coffee/bakery/farmer’s market journey!

We ordered some vegan brownies (amazing), but my sister got the best baked good… Their classic dough-muff. It is pretty much what it sounds like — a donut in a muffin form.  Move over cronut, there’s a new mash-up pastry in town! Make sure you grab one (or 3) and enjoy it on the cozy couch inside below the Mr. T framed photo…. and a bike (that I’m not sure is decor or for riding). Who knows, but we’re still thinking of that dough-muff!

Stop #6: Dinner and Shopping at St John’s Town Center

Sadly, it’s our last stop. All good journeys must come to an end. Later that night, we all headed to shopping mecca St. John’s Town Center to pick up a few last minute items (and besides, Kevin can’t pass up any trip to a Barnes and Noble). This is a massive outdoor mall that has over 150 shops, conveniently all in a row for you to burn your paycheck in one night! For those who don’t like to shop (and certainly, not members of my family!), there are plenty of places to just hang out including a turtle pond or the dog park. There are a lot of places to eat, but we recommend Moxie Kitchen and Cocktails, located just across the street from the mall. My dad loved the old-time Moxie soda they served (which tastes like a mixture of Coke, Dr. Pepper and Robitussin).

There are a variety of seating options from the upstairs bar, to the casual outdoor tables to the fun booths near the kitchen where we sat.

If you’re there late (like we were) be sure to ask for their late-night menu with some items as low as $5 a dish. We had a really fun time, and bonded with our waiter. Or at least probably gave him a story or two as Kevin pointed out the spelling error on one of their posters advertising their locally-“soured” food (rather than locally-“sourced”!). Though, our waiter was quick to point out they did have pickles on the menu. Touché!

And there you have it! A full day of coffee, shopping and eating. But even with all that caffeine, we didn’t have any issues falling asleep that night. Clearly, we pack in a busy day!