Known for being the oldest city in the United States, everything you will find in St. Augustine revolves around the city’s rich history. But there is much more to be explored in this famous Northern Florida town.
In addition to having a rich history, St. Augustine is also home to fabulous beaches, outstanding dining, high-end craft cocktail bars, and so much more! If you are looking to visit for a weekend, this is the 48-hour itinerary we recommend for getting the most out of your trip!
Day One – BBQ, Trolley Tour, Seafood, Cocktails
Our first stop in St. Augustine is going to be lunch at the outstanding Mojo BBQ Old City. Mojo is a Northern Florida staple that specializes in putting their own twist on regional classics like Carolina Pulled Pork Shoulder and Texas Brisket. Make sure you start with their famous onion rings!
After kicking off our trip with a little BBQ, it’s time to get more familiar with St. Augustine on the Old Town Trolley Tour. This 23-stop tour will show you all of the best things to see and do in St. Augustine, and you can feel free to get off and explore at any of the stops.
For dinner on our first night in St. Augustine, we’re heading to Catch 27. Everyone wants to have seafood on their first night along the coast, and Catch 27 is the best place in town for fresh-caught fish, shrimp, and clams.
Following dinner, we are taking a quick stroll around the block for a nightcap at Prohibition Kitchen. This is a great place to eat if you have more time in town, but they also have a huge bar with a great selection of craft beer and cocktails, as well as live music on most nights.
Day Two – Beach, Food Truck, History, Fancy Dining
It wouldn’t be a trip to St. Augustine without a calm stroll on St. Augustine Beach, so that is going to be our first stop on our second day in town. This beach is wide and long, and the firm sand makes it perfect for a relaxing stroll with or without shoes.
For lunch, we are hitting up a local favorite called Uptown Scratch Kitchen, which is a permanently parked food truck that will blow your mind with high-quality burgers, fried chicken, and po’ boys.
After lunch, our next stop will be the historic Castillo de San Marcos. It is the oldest masonry fort in the continental United States, and it has been a national monument since 1924. Take your time and explore the fort, as well as the surrounding grounds.
We will be following up an afternoon of history with dinner reservations at Preserved, where rich history is mixed with locally sourced ingredients to create one of the most amazing dining experiences you will find anywhere. Everything on the menu here is excellent, and the surroundings could not be more authentic to St. Augustine.
Following a delicious meal at Preserved, we will be taking a quick walk to The Ice Plant, where they serve some of the most outstanding craft cocktails you have ever seen. With three different types of ice, house-pressed juices, and locally made spirits, the cocktails here are truly one-of-a-kind.
And if you happen to feel like staying out late, there are more than a few local tour companies like GhoSt Augustine that will be happy to show you the haunted side of St. Augustine.
Day Three – History, Brunch, Shopping
We’re starting our last day in St. Augustine at the Lightner Museum, which houses one of the largest collections of fine and decorative 19th-century art in the country. On top of the impressive art collection, this former hotel is stunningly beautiful and worth visiting simply for that reason.
For our last meal in St. Augustine, we are heading to The Blue Hen Cafe. This is one of those special places that the locals frequent, and you won’t believe how good the corned beef hash tastes!
Before heading out of town, feel free to stop and take a stroll down St. George Street. You will find all kinds of interesting boutiques and gift shops here, which makes it the perfect place to grab a few souvenirs to remember your trip.
Where to Stay in St. Augustine
Because there is so much history in St. Augustine, you are definitely going to want to stay in one of the many boutique hotels around the area. One of the absolute best options is The Collector, which offers the perfect combination of luxury accommodations in a friendly setting.
For a more budget-friendly option, you could also check out The Saint Augustine Beach House or Marker 8 Hotel. Both offer outstanding views, first-class accommodations, and a price that won’t break your budget.
After spending 48 hours enjoying the history of St. Augustine, it won’t be long before you start planning to come back for another visit. And thanks to the broad experience of your first trip, you will know exactly where to spend your time when you return!
Want to Stay a Little Longer?
If you are thinking of making St. Augustine your permanent home, you should check out Freedom at San Salito.
Freedom at San Salito is a 55+ neighborhood, located in St. Augustine, Florida that offers a low stress, low maintenance lifestyle. Located off State Road 16, residents will have easy access to a variety of public amenities. The community features include a gated entrance, private amenity center clubhouse and outdoor pool. Freedom at San Salito also has a part time Lifestyle Director who cultivates the ideal selection of clubs and events for homeowners.
The newly opened Freedom at San Salito’s amenities include an amenity center with a pool and covered patio, outdoor fireplace, two bocce ball courts, and a dog park. Residents of Freedom at San Salito also have access to the master community’s amenities which includes a clubhouse, multi-purpose room, pickleball courts, tennis courts, exercise room, and outdoor pool with patio. San Salito is close to the beach, golf courses, fantastic shopping, dining, music and entertainment!
Homes range in size from 1,585 to 2,033 square feet of living space, and include features like granite countertops, walk-in closets, and covered lanais. Prices start in the mid-$250k’s.