Things to do in St. Augustine, Florida

Things to do in St. Augustine, FL

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For the longest time I didn’t know anything about St. Augustine, a city on the Atlantic in Northeastern Florida. In fact, I hadn’t even heard of it! How did I not know about the oldest city in America? Yes, second to San Juan, Puerto Rico, St. Augustine, founded in 1565 by Spanish explorers, is the oldest city in the United States.

Once I started seeing photos of this historically and culturally rich city, with its European architecture, I knew I had to find a way to visit. For what grabbed my attention the most was just how different it looked from the rest of Florida – nevermind the Palm Beach and Boca Floridian style so typical of the rest of the state, St. Augustine looked completely European through and through.

I was finally able to visit the city after my good friend Colleen moved to Jacksonville from New York City. I went to visit her and said that one thing I must do is see St. Augustine. She had visited the town a bunch and agreed. A 45-minute drive from JAX, it’s the perfect day trip.

There’s a lot to see in one day, so a weekend may be preferable to many people, however one day is sufficient as well, if you just want to wander the streets and eat good food, which is what we mainly did. We wanted to soak up the vibe and drink and have fun, without feeling like we had to tick everything off the list. And that’s what makes St. Augustine so great – because it’s very European feeling in nature, wandering the streets aimlessly is a totally acceptable activity!

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Things to Do in St. Augustine

As I said, just walking around St. Augustine is probably the best way to enjoy this picturesque city, but there’s also several sites to see as well. Here’s our list of top things to do.

Walk along St. George Street

This pedestrian only street in the Colonial Quarter is in the heart of St. Augustine and the buzz of the city. It’s a great place to get aquainted with the town and take in all that it has to offer – colonial architecture, good restaurants, live music and fun shops. Though very crowded, it is for a reason – it’s charming and quaint and full of energy. The streets surrounding St. George should be explored too; wandering around, you do not feel like you’re in Florida, but in some European outpost!

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Explore the Castillo de San Marco

Probably the most popular tourist attraction in St. Augustine is the Spanish fort Castillo de San Marco. Set on the water right in town, you can’t miss it. It’s the oldest masonry fort in the U.S. and can be seen by tour or on your own. We chose to see it on our own. You can walk along the outskirts and climb to the top where the cannons were shot. In all honesty it was blazing hot the day we were there, so we only saw it briefly from the outside.

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Visit Flagler College

Visiting a college may sound random, but Flagler College has some of the most stunning architecture in St. Augustine. In fact, this was probably my favorite thing that we did in the city. The Spanish Renaissance buildings that make up the college are truly exquisite and should be seen when in St. Augustine. Built by millionaire Henry Flagler, they originally served as the Hotel Ponce de Leon, with magical rooms such as the Dining Hall, full of Tiffany gems. Tours are offered twice daily, but even just seeing it from the outside is a treat in itself.

Take the Old Town Trolley Tour

This hop-on/hop-off trolley is a great way to see the city and get oriented. I have a thing for hop-on/hop-offs, because they are a very easy way to get aquainted with a place, and are very relaxing! We took the Old Town trolley in full and never actually hopped off, because it was so pleasant cruising around. Plus, we saved all our energy for walking the streets of the historic district.

Visit the Old Jail

Another popular activity, people love visiting the Old Jail not only because it’s so historic (it served as St. Augustine’s jail from 1891-1953), but also because of its back story. When Henry Flagler opened the upscale Hotel Ponce de Leon, he wanted a safe and secure environment, and wanted it to look that way too. So he built the jail to resemble a Victorian house and blend in with the rest of the city. Visitors had no idea it was in fact a jail. There are guided tours both day and night that tell the stories of the people – and families – that were jailed there.

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Enjoy St. Augustine’s delicious restaurants

St. Augustine is known for its food scene and I can attest to the fact that it’s very good. There are many a restaurants, patios and bars with excellent dining, drinks and live music. St. Augustine takes pride in its food culture, and its evident everywhere you walk. We had very good meals at Harry’s Seafood Bar and Grill and The Floridian. Both have great bar scenes and outdoor dining as well.

Also to be noted (but we did not go) are the St. Augustine Distillery, located in a 100 year old renovated ice factory, and its restaurant the Ice Plant. By all accounts they make for a fabulous St. Augustine experience.

And those are our top things to do in St. Augustine. Have something to add? Please leave in the comments below.