Assuming you aren’t staying downtown, you’re going to need a place to park. Your best bet is either the Visitor Center on South Castillo Dr. ($12) or since you also need a plan for getting around, the Old Towne Trolley. For around $24, you can park for free at the Old Jail and gain hop-on-hop-off trolley access complete with a pretty informative and engaging 90-minute history lesson.
If you need breakfast right away, run over to Drake’s Deli (3 blocks from the Old Jail) and grab a breakfast sandwich. But if you can wait — I really hope you can wait — hop on the trolley and take it to stop #5, “Old City Gates”. From here, head to Maple Street Biscuit Company via St. Augustine’s famous St. George Street. This historic pedestrian-only street is filled with Spanish Colonial architecture, unique shops, restaurants and art galleries. As you wander down St. George Street, take notice of the “Oldest Wooden Schoolhouse in America” on your right. No one knows just how old it is, but it’s definitely been around for at least 300 years. After snapping some pictures and cooling off a right on Cuna St and a left on Cordova will take you right to the mouthwatering Maple Street Biscuit Company.
After breakfast, continue down Cordova to Flagler College. Flagler used to be the Hotel Ponce De Leon (built by the railroad magnate Henry Flagler in 1888) and is incredibly beautiful. Even if you don’t think you’re up for all the ritz, jump into one of the historical tours of the campus — you might find the stories about Flagler’s life and accomplishments fascinating.
When you’re through with Flagler, wander across the street and explore the plaza by the Government House, peek inside the Cathedral Basilica (notably known as “America’s First Parish”), and then make your way over to the corner of Hypolita and Charlotte for a refreshing cool down at The Hyppo. These all natural, pure fruit popsicles come in completely insane and delicious combinations like Blackberry Clove, Honeydew Basil, and Chipotle Peach.
You’ll want to try several flavors but break away — there’s so much more to savor here. From Hyppo’s, take the trolley (there’s a stop right out front) straight to my next favorite place, the St. Augustine Distillery. This young and unique, locally sourced and owned distillery is housed in St. Augustine’s first power and ice company (built in 1907). They’ll show you around the facility, share their unique story, and even mix up a couple of drinks for you to sample — all for free. And if they don’t tell you, be sure to ask how they creatively broke through the state’s bureaucratic and outdated red tape.
If your visit wraps up prior to 2pm, visit the Ice Plant Bar (located on the backside of the Distillery) for a one-of-a-kind 1920s speakeasy farm-to-table lunch experience. Here you’ll find some ridiculously good-looking bartenders creating the perfect cocktail by carving ice each day from large blocks, the old-school way. If it’s after 2pm, don’t stress it. You can always come back for dinner or a late night drink. They’re open until 2am.
At this point, you have a few choices for the afternoon. You can walk over and check out the San Sebastian Winery (also free), explore the Castillo De San Marcos, drink from the Fountain of Youth (be warned, it doesn’t taste so good), check out some of the stops along St. Augustine’s Freedom Trail, or finish up your history lesson on the trolley and make your way back to your car to hit the beach.
If you’re going to the beach, I suggest heading over to St. Augustine Beach via the Bridge of Lions (if you don’t have a car, no worries, the trolley has a shuttle that will take you). Walk on over — barefooted and in your bathing suit, if you want — to Beachcomber Restaurant on A Street. This casual beach shack is the only restaurant that’s actually on the beach. It has on-site customer parking, a great drink menu, and gator bites — which you must try because honestly when else are you going to get the chance?
After a quick shower and change of clothes, find your way back downtown. At this point — after 5pm — all city parking is free so just find a spot wherever. (Try the big lot by the Castillo De San Marcos.) When you’re ready for dinner, giveMojo BBQ or the Floridian a try. But make sure to save room for dessert or, at least, coffee because you’re not going to want to miss the paradise that is Crucial Coffee’s garden.
When Crucial Coffee closes up around 10, go people watching on St. George Street and dance along with the buskers or grab drinks someplace eclectic like Planet Sarbez.
And here are 10 tips to further your experience…
1. Check out Augustine.com for a list of events — many of which are free concerts and exhibits.
2. For incredible views, climb the St. Augustine Lighthouse on your way to the beach.
3. Visit in the spring or fall when the weather is a little cooler.
4. The St. Augustine heat is no joke so freeze a couple bottles of drinking water the night before. This way they’ll stay cool all day and you can keep hydrated.
5. You can view Michelangelo’s David while in St. Augustine — sort of. The world has only two exact replicas of this masterpiece and one can be seen for free in the gardens of Ripley’s Believe It Or Not Museum.
6. Keep your mother happy and remember to put on sunblock.
7. Purchase your trolley tickets online to save about $2.50.
8. Looking to get out on the water? Check out St. Augustine Eco Tours.
9. Want to connect with something a little paranormal? Check out a Ghost Tour.
10. Most importantly, don’t let this schedule keep you from stumbling upon something new and unexpected.