My guide on what to see and do while visiting the Oldest City in America!
Living just a half-hour away from many of the attractions in St. Augustine, Florida, I’ve had the pleasure of visiting St. Augustine, the oldest city in America, many times and on several occasions. I’ve visited St. Augustine for date nights, to entertain out-of-town family, for homeschool field trips, to create travel content for our YouTube and Newsbreak channels as well as our blog, and just for a day of fun. Based on my nine years of personal and business experience, I’ve compiled my top 10 must-dos to fully appreciate the charm, beauty, and history of the Ancient City. The list is in order too. From what I believe may be the most important activities to enjoy while in the city to what’s nice to fit in if time allows. The article contains links to websites as well as links to videos of our experiences in St. Augustine, Florida to better assist you with your vacation planning. Now, on to the list!
- Take a Tour
St. Augustine was founded in 1565 and is the oldest continuously occupied settlement of European and African-American origin in the United States. That means that this city offers over 450 years of history! And this history involves many different groups of people and ethnicities- Spaniards, British, Africans, African-Americans, Minorcans, pirates, colonists, and even more. You can walk around the historic downtown of St. Augustine and gather facts and bits of history as you roam but to get a more complete picture of the history of St. Augustine, it’s essential to take a tour. Both Old Town Trolley Tours and Red Train Tours provide ride-along tours of the city highlighting key moments and people throughout the 400-plus-year history of the city. Old Town Trolley Tours also offers a hop-on and hop-off option which is a great way to get around the city. There are also walking tours offered by Tour St. Augustine Inc. as well as other companies. Some tours speak on the general history of the city, while others focus on specific parts of the city’s history like the history of piracy in the city and the development of St. Augustine by Henry Flagler. There are also ghost tours, scenic boat tours, horse-drawn carriage tours, and still more. We’ve personally enjoyed filming and sharing our experience on the Old Town Trolley Tours, Red Train Tours, and several walking tours offered by Tour St. Augustine Inc. Just click on the links to capture a more complete look at the overall history of the city.
2. Visit the Fort, the Oldest Structure in St. Augustine
Castillo de San Marcos National Monument or simply The Fort is not only the oldest masonry fort in the continental United States, it is also the oldest surviving structure, and visiting the oldest structure in St. Augustine makes sense while visiting the oldest city in America. Built and completed by the Spanish in 1695 to protect against attacks, the fort is now a national monument and a trove of history. On certain days, the fort has reenactments and cannon firings. Visit the fort to take a deep dive into the history of the city and enjoy fantastic photo ops of both the fort and the beautiful Matanzas Bay that it borders.
3. Explore St. George Street
St. George Street was once the main street in St. Augustine. During current times, this street is still bustling with activity. St. George Street is home to restaurants, shops, historical, sites, and attractions. You can pass through the Old City Gate, which was once the only entrance into St. Augustine, at the north end of St. George Street, and then make your way to the Oldest Wooden School House. The Oldest Wooden School House was the Genopoly home where Minorcan children were taught in the 1800s. Continue on St. George Street to enjoy the numerous dining and shopping options this historical street has to offer. You can even catch a historical saunter on some days, an occasion where living history interpreters dress in 16th, 17th, and 18th-century apparel and walk the streets of St. Augustine. And if you want to practice your saunter you can join in on the fun, watch and experience a saunter on St. George Street!
4. Take a Stroll on the Oldest Street in America
You can literally take a walk through history when you stroll down Aviles Street since Aviles Street is the oldest street in America! Once known as Hospital Street, archaeologists have unearthed pottery shards from under this street dating back to the early 1600s. This street may be old but it’s also vibrant and alive with art galleries, restaurants, and museums like the Spanish Military Hospital Museum and the Ximinez- Fatio House Museum.
So while in town, enjoy a stroll on the oldest street in America. Not sure what to expect when walking the oldest street, check out our tour of Aviles Street here!
5. Get Out on the Bay
It’s easy to see and enjoy the Matanzas Bay from the fort or from the historic downtown district of St Augustine but if you have the opportunity to get out on the water of the bay, I highly recommend it! Matanzas Bay plays an important role in St. Augustine’s history. The bay, once called The Bay of the Dancing Dolphins by the Timucua, earned its current name after the massacre of the French by the Spanish. Matanzas means slaughters in Spanish. Although the name is disturbing, the views you’ll experience while taking a scenic cruise, sailing, and being on the water are awe-inspiring. Enjoy our cruise on Scenic Cruises of St. Augustine and take a look for yourself!
6. Walk the Bridge of Lions
The Bridge of Lions spans the Intracoastal walkway and connects St. Augustine to Anastasia Island. Two sets of lions sit on both sides of the bridge. The lions on the St. Augustine side are named Faithful and Firm while the lions on the opposite side are named Peace and Happiness. Fantastic photo opportunities in front of any or all four of the lions make the nearly half-mile walk across the Bridge of Lions well worth the effort. When we made the trek across the bridge, we definitely thought so! Watch our journey across the bridge here!
7. Experience Life as a Colonist
Wonder what it would be like to be a member of a new colony? The Colonial Quarter Living History Tour takes you back in time to experience how citizens lived, worked, and played during the early years of St. Augustine in a fun and interactive way. It’s a thorough and entertaining lesson about how St. Augustine was established and managed to thrive despite the sometimes harsh circumstances. Plus, the views of the historic city from the 35-foot watchtower can not be missed! If you want an early look of the views of the city from the top of the Colonial Experience’s interpretation of a Spanish watchtower, watch our experience at Colonial Experience and take the 35-foot climb along with me!
8. See Where it All Began
The Fountain of Youth Archaeological Park is an attraction where you can drink from the legendary Fountain of Youth, a spring recorded in a 17th-century Spanish land grant. At the Fountain of Youth, you can also enjoy several exhibits, watch weapon demonstrations and cannon firings, plus observe and even feed wild peafowl! It is also the site of the first St. Augustine settlement. When Spanish explorer Pedro Melendez de Aviles founded St. Augustine on September 8, 1565, the Timucua already inhabited this land. Along with the exhibits and demonstrations at the park, the Fountain of Youth Archaeological Park provides an in-depth understanding of how St. Augustine began, including an in-depth look at the people, the Timucua, who were already here. We experienced this in-depth look for ourselves and shared all we learned at the Fountain of Youth Archaeological Park.
9. Visit A Museum
If you’re a city over 450 years old, you have a lot to share and a whole lot to display too so it makes sense that St. Augustine is home to multiple museums. Some museums are focused just on St. Augustine’s history like The Oldest House Museum Complex and the St. Augustine History Museum. There are others though that cover history that’s not entirely focused on St. Augustine like the St. Augustine Pirate and Treasure Museum. And there are even some museums that don’t come from a historical standpoint like Ripley’s Believe it or Not. There is such a great variety of museums to explore in the ancient city. My personal favorite is the Oldest Store Museum. It’s a great mix of history and entertainment as you receive a demonstration from the sales clerks of this early 20th-century store. The remainder of your visit involves a self-guided tour of products from the 19th and early 20th century. To help you determine which museum you may like to visit, join us as we take a museum tour in St. Augustine.
10. Venture Outside the Historic Downtown District
It’s easy to spend the day, weekend, or your entire stay just exploring the historic downtown district of St. Augustine, Florida. If time permits though, I highly recommend wandering away from St. George Street and the historic downtown district and seeing more of St. Augustine. I recommend visiting Fort Mose, the first legally sanctioned free black settlement in what would become the United States. The site offers an interactive and educational visitor center as well as the walkway to freedom- a scenic walk that leads to where the fort used to stand. Or you can cross the Bridge of Lions and head to the St. Augustine Alligator Farm– home to Maximo, a 1,250-pound saltwater crocodile, the land of crocodiles featuring every crocodilian species, alligators that you can feed, and other extraordinary animals. Another option is the beach and you can’t go wrong visiting one of the beaches near St. Augustine! There are several beautiful beaches in the area. Some of our favorite beaches in St. Augustine are Crescent Beach and Vilano Beach but there are others that we’d like to take you along with us to enjoy as we visit our favorite beaches in St. Augustine!
So that is my list of the top 10 activities and places I highly recommend while visiting the ancient city! Will you be visiting any of the places on the list? Which activities and places are you looking forward to? And if you’ve visited St. Augustine, which attractions make your top 10 list? We’d love to hear your plans and your must-dos when visiting St. Augustine, the oldest city in America!