The Ultimate Guide to St. Augustine Part 1

I’ll admit it — I’m a Northeast snob. When I moved down to Florida, I wasn’t particularly familiar with the historic charm or culinary delights of distinctly southern cities like Charleston and Savannah. Eventually we visited plenty of gorgeous old cities around the south, but one of my favorites is right in our backyard.

St. Augustine is one of my favorite places to spend an afternoon or evening. I even got married there. Since we are so close to the city, I thought I’d post an ultimate guide to St. Augustine. Disclaimer: this is only the ultimate guide according to me, Erin Addington.

So what makes St. Augustine so awesome? I’ll hit on the high points before delving into the must-sees (or must-eats, or must-stays).

The Oldest City

The biggest claim to fame for St. Augustine is that it enjoys the designation of “The Oldest City”… or the oldest continuously occupied settled city in the United States. People have lived there since 1565, otherwise known as a very, very long time ago. It precedes both Jamestown and the landing at Plymouth Rock. However, the British, in typical Brits-are-the-best-and-will-destroy-your-land fashion, burned down the city in the early 1700s, meaning most buildings date after that. Not that the 1700s are pretty old for the relatively young United States.

One thing that DID survive the burning of the British?


The Castillo de San Marcos

If you want something to survive, make it out of coquina shell. Duh. The Castillo de San Marcos is now controlled by the U.S. government — the National Park Service, to be specific — but was built by the Spaniards. Construction began on the fort in 1672 and over its lifetime, it was controlled by the Spanish, then British, then Spanish again, before becoming a U.S. Army fort in the 1800s. Osceola, the famed Seminole chief, was once imprisoned there.


There’s a small fee to get in, and it’s a pretty cool place to wander around. There’s also a video to catch, a few demonstrations and a pretty view of the water. Also, lots of real and replica weaponry.



IMG_5372While the fort itself was painted white back in the day, the sentry boxes were red. There’s really not much red left, but it must have been a sight to see back in the day.

IMG_5382The view from the sentry box.

IMG_5390The sentry boxes are fun ways to pose.

IMG_5393Cool door on the interior

Nights of Lights

The best time to visit St. Augustine is hands down the Nights of Lights. From mid-November to the end of January, the city is strung full of twinkling white lights, an homage to when the Spanish placed white candles in their windows to brighten the town during the Christmas season.

It’s perfect to get you in the holiday spirit (or keep you in the holiday spirit if you go in January). You’ll also find the best weather of the year — the ridiculously hot, humid summers are almost worth the cool, mild winters of Northeast Florida. There are special trolley tours and tons of people strolling the streets.



Even National Geographic says you should go see it. They named it a “Top 10 Place to See Holiday Lights,” along with the likes of Copenhagen, Belgium, Medellin and some random place in Georgia.

IMG_5448St. George Street

Every great city has a main thoroughfare, and St. Augustine’s is St. George Street. A good portion of it is pedestrian only and it boasts a host of restaurants, shops and touristy stops. The city’s original gates open onto St. George Street, leading to other historical treasures like…

the Oldest Wood Schoolhouse in the United States.


There’s also a host of cute places like the Hyppo, a gourmet popsicle shop. We picked up a pumpkin flavored pop and it didn’t disappoint. The owners are opening a second shop in Riverside soon, but the original is a must-see stop in St. Augustine. It has an adorable courtyard to enjoy your pop in.


St augustine

The Bridge of Lions

The Bridge of Lions connects downtown St. Augustine with Anastasia Island and is guarded by these bad boys:

Photo by Joel Addington.

The lions are replicas of the Medici Lions found in Italy at the Loggia dei Lanzi. The downtown end of the bridge includes a cute park and gazebo, a nice place to stop and enjoy a view of the water and watch the boats go by (and under the bridge — it’s a drawbridge).

Stay tuned for Part 2!

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