Top Tips for Your Trip to St. Augustine, Florida

The oldest city in the United States has plenty to see and do. Here are some insider tips and tricks to make the most of your trip to St. Augustine, Florida.

St. Augustine holds the title of the oldest city in the USA. It was (and still is!) the oldest continuously occupied settlement of European and African-American origin. The city was founded by Spanish admiral Pedro Menéndez de Avilés in 1565, a full fifty-five years before the Pilgrims landed at Plymouth Rock.

Bridge of Lions in St Augustine Florida
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The historic part of St. Augustine has a very quaint, European feel. It’s unique and unlike any other city in the country. Although most structures were destroyed during a British invasion in 1702, it boasts street patterns and architecture that reflect Spanish origins.

As a city that has been controlled by Native Americans, Spanish, British, Spanish (again!), and then finally became part of the United States of America, it’s full of centuries-old buildings and monuments. There’s a vast array of styles here, and it’s all blended together into this one amazing place.

Of course, all of this can be overwhelming, to say the least. There’s just so much to see and do. If you want an authentic and interesting — not touristy and cheesy — visit to the Oldest City in America, where do you begin?

If you’re planning a trip to St. Augustine, you’re in luck! Here are a few insider tips and tricks to make the most of your vacation in St. Augustine.

Spend Some Time Just Walking

St George Street in St. Augustine, Florida
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With the brick roads, the intimidating lions at either side of the Bridge of Lions, the view of boats across Matanzas Bay, and all of the historical architecture, St. Augustine has a lot to take in visually. It’s easy to miss things.

Throw on some sneakers and spend a little bit of time just walking and exploring your surroundings. You’ll notice hidden courtyards and other secrets that you would have missed otherwise.

Visit During the Right Time

Some two million people visit St. Augustine each year, making it difficult to avoid crowds. While there isn’t necessarily an “off” season for the city, avoiding peak travel times means you get to see more. Crowds are largest from June to August, so it’s best to avoid those months.

The best time to visit St. Augustine is usually between March and May. The weather is comfortable, and there are fewer crowds. Or, try December through February. While the lows usually hit the mid-40s, daytime temperatures are a mild 70 degrees F.

Skipping September through November is also recommended. This falls within the area’s hurricane season, and you stand a chance of encountering terrible weather.

Take a Sightseeing Train

tourists riding a sightseeing tour train trolley in St Augustine, Florida
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This may sound like a really nerdy, touristy thing to do. I mean, it is, and I’m not going to pretend it’s anything else. But in all reality, in a city full of crowds, with very narrow roads and more things than any one person can see in one trip, these sightseeing trains are going to be the best part of your vacation.

You’ll learn all kinds of interesting history about what you’re looking at, including facts that only locals can tell you. The best part about these trains, though, is the fact that they drive you around all day long. If you haven’t been to St. Augustine before, you probably have no idea how difficult it’ll end up being trying to find parking spots. After all, the city was built before cars existed.

Enjoy Escargot Inside of a Pool

What is now the Lightner Museum was originally the Hotel Alcazar, built by railroad tycoon and hotel developer Henry Flagler. It is a magnificent example of Spanish Renaissance architecture.

The hotel once boasted the largest indoor swimming pool in the world. That swimming pool is now home to Cafe Alcazar, an elegant eatery serving refined New American fare for lunch seven days a week and dinner once a month. Reservations are not required, but they are highly recommended.

Tour the Castillo de San Marcos

Castillo de San Marcos in St. Augustine, Florida
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The Castillo de San Marcos is the oldest masonry fort in the continental United States, located on the western shore of Matanzas Bay. After 251 years of continuous military possession, it was only deactivated relatively recently, in 1933. You can walk the grounds outside for free, and you can purchase a ticket to tour the inside at your leisure.

I do really suggest that you follow a tour guide through the fort to take it all in. They will be able to give you stories that you may otherwise never learn. They even do “historic weapons demonstrations,” which is fancy talk for shooting off cannons that have been there for a few hundred years!

It’s also worth noting that the Castillo de San Marcos is a national park. That means you should check with the National Park Service for the days they’re offering free entrance to parks during the year.

Scarlett O’Hara’s and the Ghost Bar

Head over to Hypolita St. and spend some time at Scarlett O’Hara’s. You’ll find some of the best shrimp and grits and some of St. Augustine’s finest local musicians… and a ghost or two.

While you’re at Scarlett O’Hara’s, head upstairs to the Ghost Bar. It is listed in the National Directory of Haunted Places and is said to be haunted by Mr. Colee, the man who built the house originally back in 1879. He even gets his own stocking at Christmas!

Don’t Skip the Military Hospital

The Spanish Military Hospital Museum in St Augustine, Florida
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Located on Aviles St., the oldest street in the Continental United States, sits the Spanish Military Hospital Museum. It’s kind of a hidden gem. In fact, the last time I visited, there were only a handful of people there for the tour — but people must not know what they’re missing out on, because this was definitely a unique experience.

The museum focuses on the “cutting edge” medical practices of the Colonial era, during the Second Spanish Period in St. Augustine. They cover the surgical practices of the day, show you the tools, let you see ward beds, and give you a tour of the medicinal herb gardens. The Apothecary will show you how medicines were created and how herbs were the origins of some popular medicines today.

Of course, if you really want a unique experience, show up on a Friday or Saturday evening. This adults-only tour is all about the “chilling truth of humanity’s medicinal past.” Called Quackery: The Dark Side of Medicine, the museum says this one’s “not for the squeamish!” Reservations are required for this tour.

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