A 2 Day St. Augustine Vacation Itinerary For Families

St. Augustine is one of the premiere northeast Florida destinations, a frolicking fun place to visit for beach lovers, nature admirers, and anyone who likes to explore a gorgeous historic city downtown.

St. Augustine Condo Rental

St. Augustine condo rentals provide a perfect opportunity to check-in and unpack with ease. And you don’t have to go far to have some quick fun on your first day. Head right to the beach or walk around the landscaped garden paths at the resort. We always recommend you take some time to relax, in style, before hitting the events and getting to the many (many) possible activities in the city. 

Once you have had some time to get used to living by the beach, it’s time to start your adventure. Here’s how we recommend getting the absolute most out of just 48 hours in St. Augustine.

st augustine bridge
Photo from Shutterstock

Day 1 in St. Augustine

So you got your feet wet as a first-time visitor? Now it is time to really see the sights and sounds of St. Augustine. Here’s how we would follow day one.

  • Breakfast at Blue Hen: The Blue Hen has one of the definitive breakfast experiences in Lincolnville, at the southern end of historic St. George Street. This comfortable café hosts pancakes, chicken and waffles, delicious fresh orange juice, and more with a clever architectural edge towards Old Florida homes. The Blue Hen Café is only open from 8 a.m. to 2 p.m. so be sure to get there early. There is also often a wait on weekends and there is no call-ahead so plan accordingly. Fortunately, the neighborhood is lovely, with sprawling Spanish moss hanging by the building. It has its own parking lot and is located at 117 M L King Ave.
  • Hop on Old Town Trolley or Ripley’s Sightseeing Train: Any smart visitor knows the most effective (and fun) way to travel is by trolley. We highly recommend getting a lay of the land after breakfast. St. Augustine has two main trolley providers. They are Old Town trolley or Ripley’s Sightseeing train, colloquially called the green and red trains respectively. Both provide virtually all-day access to most of the city’s downtown sites. Entrance is usually unlimited for the whole day with a visitor’s pass, and you can get on and off as many times as you see fit. Tours are fully narrated, so it is more than just a casual and cool mode of transportation. If you plan on hitting many top sights in one day, like Ripley’s museum, the Old Jail, and the fort, we recommend booking your day pass today.
  • See the Historic Wooden School House: After you meandered and journeyed to some sights, even viewing them from your trolley, we suggest getting on foot and checking out historic downtown St. George Street. Housed on this major walking cobblestone road is the oldest standing historic wooden schoolhouse. This single-room wooden construction protects and preserves Minorcan history dating all the way back to the 1700’s. Visitors can see how students were educated and what they learned. The school is also located by a historic school kitchen and the gardens, all part of any tour. Get a feel for life in historic St. Augustine in this authentic and original American treasure. 
  • Lunch at Casa Maya: Casa Maya is a fantastic Latin-inspired seafood restaurant downtown. It has a really upbeat vibe and injects some serious energy into every visit with its Latin music and fun attitude. The outdoor patio is a fantastic place to pop in for lunch. It has a handful of vegetarian favorites, as well as excellent specialty seafood sandwiches. The upstairs deck also adds a nice atmosphere as you enjoy menu favorites like ceviche, fajitas, and incredibly large stuffed burritos. Casa Maya is open from 10 a.m. to 10 p.m. every day. 
  • Pirate Treasure Museum: The Pirate Museum celebrates everything pirate-themed in St. Augustine and is one of the best kid-friendly activities in downtown. This private collection, laid out and organized for your viewing pleasure, boasts some incredible pieces. See genuine pirate booty in the form of gold coins. Take a walk through multiple rooms, seeing the stories of pirate lore both completely true (and sometimes exaggerated). Who really was the best pirate of the seas? Was it Thomas Tew, famous for fighting after getting blasted in the chest with a cannonball? Was it Blackbeard, the great trickster of the open seas? Was it one of the merry women, like Grace O’Malley? The pirate museum also features real pieces from famous pirate films, like Pirates of the Caribbean. The gift shop lets you take a little piece of the pirate adventure home.
  • Dinner at The Floridian: The Floridian is THE downtown restaurant. A gorgeous ambiance from the outdoor patio lighting really sets the stage for a phenomenal night of food. The Floridian uses strictly local ingredients, all fresh, making small adjustments to the recipe based on seasonal availability. The fresh fish is local and changes almost daily. Entrée-sized salads leave even lettuce lovers quite satisfied by the size. We recommend the double whammy of the Fried Green Tomatoes and the Fish N Grits, both southern staples and exemplary additions to your vacation experience. If you have some extra time, complement your evening with a visit to the downtown winery.
  • Popsicles at Hyppo or Peace Pies: Hyppo and Peace Pie: no St. Augustine vacation is complete without a step in either of the city’s best dessert stops. The Hyppo is a regional favorite, offering fresh juice popsicles in a wide variety of flavors. Peace Pies offers cookie and ice cream sandwiches, with a rotating selection of, literally, over 500 different cookie/ice cream combinations.

After day one, you can return to the St. Augustine beachfront resort and sleep soundly. Fortunately, you got another whole day of adventure ahead!

Plan Your Trip

That is an overview of two whole days exploring the best of the city. Now, find the finest St. Augustine condo and make it happen!

Day 2 in St. Augustine

  • Breakfast At Café Eleven: We recommend sticking beachside for the time being and nabbing breakfast at Café eleven. The welcoming outdoor patio means you can enjoy the fresh morning air as you indulge in some awesome specialty sandwiches. Selections include ham, brie, pesto, meatloaf hash, eggs benedict, and even a breakfast pizza. Café Eleven is open daily, without fail, from 7 a.m. to 9 p.m. it is located at 501 A1A Beach Blvd.
  • Hit The Beach or Visit Anastasia State Park: If you haven’t made the time to see the beach, now you must. We recommend staying beachside by A Street due to its parking lot and close proximity to Café Eleven. There is also a parking lot on the northern side of Anastasia Island. If you head north on A1A, you won’t miss it. Regardless of how you enter the beach, stay for the soft waves and white sands. If you want more “activity” in your breach experience, we recommend Anastasia State Park. While the entrance is $8 per vehicle, you get access to multiple nature trails, kayaking drop-in points, sensational water, and marshland overlook, security, and more. It’s 1600 acres of protected land, and worth the visit for anyone who wants to indulge heavily in the city’s natural side.
  • Lunch: We would be remiss if we didn’t recommend two of our top favorite lunch spots. The first is Pizalleys downtown. While many visitors head across the street for Pizza Time’s New York-style offering, we love the vibe and style of Pizalley’s. Pizza by the slice can be custom-built. Though non-pizza lovers may get more out of our second favorite lunch spot. St. Augustine Seafood Company, another downtown stop, has all seafood lovers may ask for between big (and we mean big) fish sandwiches and thick French fries. The fish sandwich is a fresh catch, so expect an option like Mahi. 
  • Visit the Alligator Farm: The Alligator Farm is spectacular. As the country’s largest alligator zoo, it houses literally dozens of alligator and crocodile species, next to other animals, like the lemur, python, and sloth.
  • Spanish Bakery: We recommend getting a few post-dinner goodies at the Spanish bakery before they close at 5 p.m.
  • Eat at Sunset Grille for dinner: Sunset Grille is the definitive seafood restaurant by the water. This big two-story building showcases live music, beachy vibes, and big cocktails. It’s not-to-be-missed for anyone who wants that fun Florida eating experience.