How First-Timers Do St. Augustine, FL: The Oldest City in the Nation

Are you really even American until you visit the first and oldest city in the United States? 

Sorry, New Englanders. Long before Jamestown and Plymouth Rock, there was a small, coastal settlement founded by Spanish admiral, Pedro Menéndez de Avilés, in 1565.

The city is St. Augustine. The location is the northeast corner of Florida, just south of Jacksonville.

Like most stories of colonial conquistadors, this one entails a long history of bloody battles between European settlers, the Spanish and Native Americans. For centuries, Florida switched hands between the British and the Spanish until 1821 when the U.S. was able to negotiate the purchase of Florida as a U.S. territory.

I finally visited St. Augustine for the first time and compiled a list of must-dos for first-timers (aka the things I enjoyed as a first-timer). This list is not all-encompassing, as 3-days wasn't enough to pack it all in and we are already planning round two! 

Visit the Castillo de San Marcos National Monument

Considered the oldest masonry fort in the continental U.S., Castillo de San Marcos is constructed of coquina, a soft limestone rock made of broken shells. This porous material enabled the fort walls to absorb cannonballs, rather than breaking apart like rock or wood.

Instead of bare rooms, history comes to life with staged artifacts, fact boards, impersonators, video reenactments and even live cannonball firings. 

There is a small entry fee for adults, but your pass will get you back in all week. (Free admission for children and seniors). It can take a couple hours to explore all that awaits you in this 345-year old fort so plan accordingly.

Explore Historic Colonial Downtown

St. George Street, located directly across from Castillo de San Marcos, is the heart of the historic district. This quaint, pedestrian-friendly street is lined with locally-owned boutiques and eateries. 

You won't find any big box retailers, airbrush t-shirts or sword shops here. Instead, delight yourself with handcrafted gifts and jewelry, coastal decor, cigar shops, bakeries and historic buildings such as the oldest wood school house in the USA. And an unusual number of ice cream shops. 

The street can be crowded and most locals tend to avoid this tourist haven, but it's fun to explore for an hour or two. I scored a snazzy, straw brim hat to avert the scorching sun and wore it religiously for the entire trip. I noticed many other visitors appeared to do the same.

Eat & Drink

As a devoted Yelp-aholic, I tend to take the star rating system as law. Right or wrong, I shoot for 4 stars or better. Here are some of the places that exceeded my dining expectations. 

Cap’s on the Water - where palmettos line the beach and fiddler crabs scamper back into their driftwood homes. Yes, I said palmettos and beach, in one true, Old Florida setting. 

Cap's is ideal for drinks on the water, top-grade oysters and luscious garden-canopy vibes. Situated on the Tolomato River, massive oak trees sprout out from the wooden deck and even inside the "Florida room" dining area. Antique chandeliers and string lights lead the way to the laid-back bar on the back deck.

Did I mention the Oyster Eating Championship transpires at said bar on the back deck? And that the standing champ (Joe LaRue) ate 45-dozen oysters in one hour? (That's 540 goobers of goodness). May the odds be ever in your favor if you dare. 

Cap's menu features fresh-caught, local seafood paired with traditional Southern and Mediterranean flavors. Our table didn't have a single dish that disappointed, but you can't go wrong with the catch of the day, prepared your favorite way. As a cheesecake aficionado, the sea salt caramel cheesecake was the star of the dessert tray.

The Ice Plant - almost a century ago, the building was originally used as (you guessed it), an ice plant. When you enter the doors, you are stepping back in time down to the last 20th century detail.

Known for their handcrafted cocktails, locally-sourced menu and their mission to return to the craft of ice harvesting by freezing purified water in large blocks. Would you prefer your ice shaved, pebbled or shaped as a 1" rock? 

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We visited on a Saturday afternoon to find that they were only serving brunch, which turned out to please everyone. 

To start, we ordered the smoked local fish dip served with pickled okra and Old Bay seasoned, housemade chips. Amazing. As an I entree, I ordered the short rib hash and farm eggs, every bite a unique blend of flavors. 

General lesson: if you're a lady ordering a drink, do not tell the server "surprise me." 95% of the time, they will come back with a froo-froo sweet pink drink (not pictured for obvious reasons). Just say 'whiskey' for heaven's sake.

After your meal, visit the St. Augustine Distillery located in the same building for rum tastings, cocktail-making seminars and to purchase their small batch hand-crafted spirits. 

The Bar With No Name - head across the street after exploring Castillo de San Marcos and cool down under the shade of a palm tree with an ice cold beer and the Matanzas River breeze.

No Name Bar has a large outside deck with a view of the fort and the river. Dive bar ambiance and live music six days a week, it is also a good nightlife option. 

Maple Street Biscuit Co. - This quirky joint serves up signature biscuit sandwiches and locally-roasted coffee in a friendly, upbeat atmosphere. 

Their most popular sandwich, the Squawking Goat, contains all-natural fried chicken and a fried goat-cheese medallion stacked high on a flaky biscuit and drizzled with house-made pepper jelly.

A few restaurants on the roster for next time: The Floridian, Mojo Old City BBQ, Columbia Restaurant, and Prohibition Kitchen.

St. Augustine Lighthouse & Maritime Museum

Enjoy the best views in the city. Don’t go with the expectation of burning lots of calories after your culinary binge-fest. The sign states you will burn 24 calories climbing up the 219-steps and 11 more on the way down.

Preceded by wooden watchtowers in the 1500's, the St. Augustine Lighthouse was constructed in 1871 and is the oldest surviving brick structure in St. Augustine today.

Lightkeepers lived on the premises with the important role of keeping the beacon lit until the tower was automated in 1955. 

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The Great Cross

The Great Cross was erected in 1966 as a symbol of the founding of St. Augustine and the start of Christianity in America. The cross stands 208-feet tall and acts as a “Beacon of Faith” to all who pass by it.

Located at Mission Nombre de Dios on the Matanzas River, you can see the cross standing sky-high from the St. Augustine Lighthouse on the opposite bank.

Flagler College

Before Flagler College was an academic institution, it was the luxurious Hotel Ponce de Leon, a masterpiece of Spanish renaissance architecture constructed by Henry Flagler in 1888. His vision was to create a playground for the rich.

The college was founded later in 1968 and has become a cornerstone of the architectural heritage in the city. The campus has grown to 49-acres, covered with fountains, wrought-iron chains and gates and beautiful, intricate detail in every direction.

Sunrise Bike Ride

We learned quickly that the heart of the city can get pretty crowded. Take advantage of an early morning bike ride to take people-less photos, explore the historic neighborhoods and catch a sunrise over the Matanzas River. 

Consider visiting during the fall or winter months when the temperatures are cooler (“cooler” being a subjective term in Floridian speak). We visited near the end of June and temperatures were in the mid-90’s during the day. Avoid spring break and summertime which are the busiest times of year.


What did I miss in this list of must-dos? Comment below with your recommendations!