Around the World- St. Augustine, Florida

Around the World- St. Augustine, Florida

A few months ago I launched a series called “Around the World.” Each installment features a different city with insider tips on where to go and what to do from someone who lives there. (and whose taste I trust) 😉 You can read about New York City here and Denver here. I have a few international cities coming soon…can’t wait!

If you have been reading my blog for more than 5 minutes you probably know that I love to travel. I have a passion for exploring new cities and experiencing different cultures. I frequently scour the internet for information before I go somewhere and almost always buy some type of travel book to take with me for tips along the way. Not surprisingly though, I’ve found that the best resources are the locals. They know exactly where to go for the best food, how to beat the crowds, what part of town to stay in, and what you absolutely must see while in xyz city.

This time, we’re heading down south to St. Augustine, Florida.


St. Augustine will always have a very special place in my heart as I spent my college years in this quaint little seaside town while attending Flagler College. But, times have changed and the places I thought were cool back in the late 1990’s (very late 1990’s thank you) are either no longer around or not the type of place I would promote on my blog. 🙂


Our Host: Steven Fortunately for me, I have a brother-in-law who is the perfect person to assist me with this series. Thanks to Steven’s job as the Associate Director of Admissions at Flagler College, he lives and breathes historic downtown St. Augustine. He’s a history buff, bona fide foodie, appreciates a good craft cocktail, and always knows exactly where to go and what to do.

 How long have you lived in St. Augustine? I have lived here for 10 years, but have been visiting and going to school here for at least 22 years.

What do you love most about the city? I love that St. Augustine has so much rich history. It is the oldest continually occupied European settlement in the United States, and fondly referred to as the “Oldest City” to locals. A downtown population of less an 14,000 people, St. Augustine feels like a small town, but benefits from the tourism; fantastic restaurants, incredible live music, a decent art scene, and of course, all kinds of eclectic bars. The best part of living here is the walkability of all of these places.  

What’s your biggest gripe? The tourism industry can be both a blessing and a curse. Unfortunately, parking during the high season can be tricky. (winter) St. Augustine has come a long way in terms of handling the parking in what is essentially an ancient city with old cobblestone streets, but the number of tourists over the last few years has grown due to greater exposure on the national scene.

When is the best time to visit? My favorite time is April. St. Augustine is the kind of city you want to stroll through, and like any other place in Florida, it can get really hot during certain (actuality- most) times of the year. April is usually nice because there is little humidity and temperatures are in the upper-70’s.

The end of November through early January is also a great time to visit since the city is decorated with white-strung lights during what is known as “Nights of Lights.” St. Augustine was actually listed as one of National Geographic’s Top 10 Places to See Holiday Lights.


What’s the best way to spend an afternoon? If your travels only allow for a half a day, I recommend taking one of the trolley tours around historic downtown. This will allow you the opportunity to see a little bit of everything St. Augustine has to offer and you can jump on and off at any of the stops during the day.

I strongly recommend taking the time to walk around the Castillo de San Marcos and touring inside if time allows. This is a 17th century fort constructed by the Spanish to defend St. Augustine from attacks from the English, as well as from pirates! The Castillo de San Macros has flown many flags throughout it’s history and it’s worth taking the time to visit.


And if I have an entire day? If you were to arrive in the afternoon, I would recommend driving over to St. Augustine Beach and spending an hour or so walking around. There are plenty of restaurants and bars nearby for grabbing a quick lunch. I’d recommend Stir It Up, Obi’s Filling Station, or Mango Mangos– all local favorites. (Editor’s note- Stir It Up opened back when I was in college and I ate there almost every day- SO good and I love that they are still in business)

After checking out the beach, you will want to drive back downtown (10 minutes) to explore the historic side of town. You can stroll through some great art galleries during “Art Walk” which takes place during the first Friday of every month. There are some really great museums- the Spanish Military Hospital Museum, the St. Augustine Pirate and Treasure Museum (I swear this is actually really cool and legitimately historic thing), and finally, the Historical Society Research Library where you can see maps and other documents stretching back to the 16th century.


After checking out some history and art, I would stroll over to the historic Hotel Ponce de Leon, now home to Flagler College.

You are able to tour parts of the former luxury hotel built by Henry Flagler in 1888 and see one of the most beautiful college dining halls in the country. (Editor’s note- it was the 1st luxury resort in the United States and the stained glass in the dining hall was done by an apprentice by the name of Louis Tiffany. Yes, that Tiffany)


I’m feeling very thirsty after all of this walking Steven. Well, I’d recommend heading over to the St. Augustine Distillery. Built at the turn of the 20th century as the Florida Power and Ice Plant, the Distillery opened up and began producing vodka, gin and rum. The Distillery just released it’s first batch of bourbon which is actually the first bourbon produced in the state of Florida since Prohibition. Great cocktails and a superb atmosphere.

So what’s your favorite bar? A good bar that’s worth checking out right now is Odd Birds Bar. The bartenders are so knowledgeable and able to craft drinks from any spirit you ask for. The menu of drinks rotates seasonally and each bartender is responsible for creating two of the drinks on the menu.  I just tried a drink named the ‘Steven Seagull’ that included squid ink and was adorned with an oyster shell on top with a Luxardo cherry as the pearl.  Odd Birds Bar also has fantastic arepas to snack on while imbibing, along with a very trendy atmosphere.

Any restaurant recommendations? Two trendy restaurants I cannot recommend enough would be The Floridian and The Ice Plant. The Floridian has savory, southern dishes prepared from locally sourced ingredients. The fried green tomato appetizer is out of this world and the Indian Summer salad is amazing. The Ice Plant is actually connected to the St. Augustine Distillery, and you need to stop by here for a cocktail at the very least. They have one of the tastiest menus in town- try the burger! They also just started serving brunch.


What is misrepresented/misunderstood about St. Augustine? That we are a cheesy tourist town that is a pit-stop on the way to Disney World. Families have lived here for generations, stretching back to the 17th century, and it continues to be a great town to both visit and live.

Fun fact- St. Augustine celebrated the 450th anniversary of it’s founding in 2015, and the King and Queen of Spain visited along with other dignitaries.img_4555

It’s a small town, are there things to do? Other than having beautiful beaches, there are so many festivals and great bands who come through town. Mumford and Sons hosted their Gentleman of the Road Tour a few years ago, and the St. Augustine Amphitheater gets many big name bands. I’ve seen Kings of Leon, Vampire Weekend, The Avett Brothers, O.A. R. , Brand New, Death Cab for Cutie, Chvrches, to name a few.img_4538

So give us your best sales pitch- why should we book our next vacation to St. Augustine? St. Augustine is a historic, coastal city and many of the restaurants, bars and shops evoke a laid-back atmosphere. Things tend to run at a slower pace here, as they have for the past 450 years. Those of us who live here love that. If you are looking for that sense of relaxation that a beach getaway offers, along with the charm of a southern town that has a deep history and incredible food scene, St. Augustine may just be the place for you. I love living here and showing people around, so let me know in the comments section if you have any questions about the city that I can help with!


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