Exploring St. Augustine, FL: America’s Oldest City

Written by Lisa Evans

November 3, 2023
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Come along to the eastern coast of Florida to discover St. Augustine. This charming city seamlessly blends its rich history with a progressive future. Read on for the best things to do in St. Augustine, FL.

Until recently, I did not realize that St. Augustine, on the eastern coast of Florida, was the oldest continuously occupied European settlement in the United States. As a person who thoroughly enjoys history and exploring this subject, my interest was immediately piqued. I also learned that while St. Augustine celebrates its historical ties, the area embraces the modern and progressive.

This charming city and its surrounding areas overflow with the history they so relish. At the same time, they weave progress into the mix in a seamless way that does nothing to detract from the centuries that came before.

Let me take you on a journey of some of the most exciting places I visited and the discoveries I made on my quest for the best things to do in St. Augustine.

St. Francis Inn

One of the most delightful accommodations I have experienced recently is my stay at St. Francis Inn. The first impression you feel when you enter this beautiful Inn is of being home. The innkeeper greets you upon arrival, and once you have checked in, their entire staff makes you feel welcome. With this purpose in mind, they remember you by name. Beautifully themed rooms with all the modern amenities are offered at this enchanting Inn. I was lucky enough to spend my time in the Ballerina room, named so due to the lovely portrait of one adorning the wall over the fireplace mantle.

St. Francis Inn sign, bold and proud

St. Francis Inn sign, bold and proud. Photo by Lisa Evans

The breakfast buffet offers different dishes each day. A social hour every afternoon allows guests to socialize with other people staying here. I had great conversations with other travelers and learned their stories and what they found interesting while exploring St. Augustine. Each day, once your wanderings have ended, you return to the Inn to find the tasty dessert that awaits you.

Above all, my favorite place at the St. Francis Inn was the courtyard. It is simply beautiful. It was a calming sanctuary where I was able to sit and enjoy. You are barely able to tell you are inside a thriving city. The foliage, flowers, birds, and fountain surrounding you in this courtyard create an oasis ideal for your morning coffee or an evening cocktail. One of my favorite parts? Three outdoor rescue cats hang out here, receiving love and sustenance from staff and guests alike. It truly is a beautiful place to use as a temporary home.

Beautiful fountain in the Courtyard at St. Francis Inn. Photo by Lisa Evans

Beautiful fountain in the Courtyard at St. Francis Inn. Photo by Lisa Evans

Old Town Trolley Tour

Upon arrival in the city’s historic district, one of the first things I noticed was the small, narrow streets—many made of brick. Parking can sometimes be challenging—what better way to see the area than with someone else driving? I’m sure many are familiar with the name Old Town Trolley. They offer services in many cities throughout the country. Taking the trolley allowed me to hop on and off at several places to explore at my own pace. As the trolley driver said, consider the trolley your public transportation. It was some of the best advice I received during my visit.

Although I consider them tour guides, the drivers were enthusiastic and informative. I was educated on some interesting tidbits about each trolley stop. I found many other places to seek out on my next visit to St. Augustine.

You can explore Castillo de San Marcos, the oldest masonry fort in the continental US. Rising majestically over the city, it is truly a marvel to walk through.

Castillo de San Marcos turret. Photo by Lisa Evans

Castillo de San Marcos turret. Photo by Lisa Evans

Do you like the unusual? Then, stopping at Ripley’s Believe It or Not Museum would entice you to visit. You may want to tour the St. Augustine Distillery. The distillery is housed in a 1920s ice manufacturing plant and now makes craft spirits such as whiskey, rum, vodka, and gin. Likewise, you may want to visit Potter’s Wax Museum, America’s first wax museum with a dark history.

The stops are plentiful, and you will find places along the route for various interests. You won’t be disappointed. I know I wasn’t!

Artillery that protected the city of St. Augustine. Photo by Lisa Evans

Artillery that protected the city of St. Augustine. Photo by Lisa Evans

The Tasting Tours

I have so many favorite experiences from my visit to this beautiful city. By and large, an afternoon tour with Laura from The Tasting Tours ranks at the top. I was able to experience the St. Augustine foodie scene, learn some interesting stories about the city, and taste some phenomenal dishes. Our group was small and intimate and allowed for significant interaction.

I took the Corks and Forks walking tour within the historic district. Our group had a fabulous time, and the food was divine. Moreover, a drenching rain shower between the two restaurants did not dampen our spirits!

The tour began at the stunningly beautiful Treasury on the Plaza, built in 1927 as a bank and office building. However, now it is a wedding and event venue. Known as the skyscraper, it is the tallest building in St. Augustine. At five stories, its closest rival is a church steeple.

The first stop on the tour was an authentic Greek restaurant named Athena Restaurant. Here, I got to experience Saganaki, better known as flaming cheese. I cannot describe the fabulous taste; the presentation was like no other. Lastly, we sampled a lamb and beef gyro with house-made tzatziki sauce.

Saganaki cheese. Photo by Lisa Evans

Saganaki cheese. Photo by Lisa Evans

The next stop was Old City House, where we arrived drenched from the rain. Housed within its own Inn, this fine dining establishment was gorgeous. Lightly grilled shrimp with house-made sauce on a bed of vegetable risotto was on the menu.

Grilled Shrimp and Risotto. Photo furnished by The Tasting Tours

Grilled Shrimp and Risotto. Photo courtesy of The Tasting Tours

From there, we ventured to Casa de Vino 57, where we could sample five exquisite wines, choosing the one we favored most for a full pour. Casa de Vino offered a tasty charcuterie board.

A wonderful charcuterie board. Photo furnished by The Tasting Tours

An excellent charcuterie board. Photo courtesy of The Tasting Tours

For dessert, we visited ChocoLatte’s for a savory piece of cheesecake. Overall, a truly wonderful afternoon!

Cheesecake for dessert. Photo furnished by The Tasting Tours

Cheesecake for dessert. Photo courtesy The Tasting Tours

St. Augustine Eco Tours

Finally, one of the things I enjoyed most during my time in St. Augustine was an excursion with Captain Zack from St. Augustine Eco Tours. This local company is genuinely invested in the community and preserving nature and the water as it should be. I highly encourage you to experience this tour.

Castillo de San Marcos from the water. Photo by Lisa Evans

Castillo de San Marcos from the water. Photo by Lisa Evans

Offering both boat excursions and kayak tours on the inland waters of the area, St. Augustine Eco Tours offers one of the most personalized experiences on the water. The company’s captains and guides are marine naturalists who provide the utmost respect for the environment. I was lucky enough to be on a small research boat equipped with microphones and other cool gadgets that help naturalists with their work. Unquestionably, hearing a school of fish far below the bottom of our boat was fascinating!

Furthermore, St. Augustine fishing charters are available for those interested in exploring these waters with a rod in hand. These charters blend the thrill of the catch with the serene beauty of the area’s diverse ecosystems. This unique blend of eco-friendly exploration and angling excitement offers a comprehensive view of the natural wonders that make this location so special.

A dolphin playing in the water. Photo by Lisa Evans

A dolphin playing in the water. Photo by Lisa Evans

I was able to see and learn about vulnerable bird populations and the efforts Captain Zack and his team take to ensure the safety of these birds. Despite opposition, they even go so far as to become involved in local policy to change some misdeeds of the past. I saw Ospreys hunting and soaring above. I witnessed a sea turtle floating along and dolphins playing carelessly. Learning the names given to them and, at the same time, the habits and migrations of these incredible animals made them familiar. I understood the meaning of a company that puts sustainability above profit. It was an exhilarating experience.

A heron and egret seen from the Eco Tours boat. Photo by Lisa Evans

A heron and egret as seen from the Eco Tours boat. Photo by Lisa Evans

A City with Many Faces

St. Augustine is a truly remarkable city. History appears everywhere you turn. Being the nation’s oldest city is something they take pride in. At the same time, the city’s food and music scene are relevant and progressive.

St. George Street pays homage to centuries past and offers a place for local artisans, bars, restaurants, and many other businesses to thrive. Experience carriage rides, ghost tours, and historical sites of worship. Find ‘buried treasure’ at the Pirate and Treasure Museum and sip from the Fountain of Youth. Enjoy the exquisitely lovely St. Augustine Lighthouse and Maritime Museum. There is something for everyone!

The beautiful and majestic St. Augustine Lighthouse. Photo by Lisa Evans

The beautiful and majestic St. Augustine Lighthouse. Photo by Lisa Evans

Articles Related to Visiting St. Augustine, FL

Exploring St. Augustine

I encourage everyone to visit and submerge themselves in this beautiful area. For all I saw and learned on this trip, there is so much more I want to experience. I will return soon to enjoy many more adventures in St. Augustine.

For those planning their own USA trips, check out Exoticca for more inspiration. We invite you to explore Wander With Wonder for more to do when you visit Florida.

Come along to the eastern coast of Florida to discover St. Augustine. This charming city seamlessly blends its rich history with a progressive future. Read the Wander With Wonder article for the best things to do in St. Augustine, FL. | Florida's Historic Coast | What to do in St. Augustine | What to do in Florida | Best historic cities in Florida

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Exploring St. Augustine, FL: America’s Oldest City

Written by Lisa Evans

Lisa Evans is a freelance travel journalist, photographer, and author. She has always enjoyed the outdoors and nature and often includes them in her work. History is another passion. Every place haas a story to tell if only you find it. Music is another area that tells great stories if only one will listen. These passions, along with her admiration for beautiful, poignant photographs, pushes her to author stories and take photos to instill a desire in her readers to explore the world and discover new places. Lisa is a member of TraveMedia, SATW, NATJA, IFWTWA, and Travel Writer's University. She is the author of 100 Things to Do in Coastal Mississippi Before You Die, available through Reedy Press. Follow Lisa through her website WriterLisa.com and on social media at @MyGypsyTravel and @100ThingsCoastalMS.

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