There’s something special about walking through a city where history feels alive around every corner. During our recent visit to St. Augustine, Lisa and I spent the day wandering the famous St. George Street area, touring the historic jail, and revisiting one of the city’s most iconic landmarks, Castillo de San Marcos National Monument.
Even though we had visited St. Augustine before, this trip gave us a chance to slow down, soak in the atmosphere, and enjoy the charm that makes this historic coastal town such a popular destination in Florida.
Unlike many Florida beach towns, St. Augustine feels deeply connected to its history. Between the Spanish colonial architecture, brick streets, centuries-old landmarks, and waterfront views, the city has an atmosphere that feels completely different from anywhere else in the state.
- Walking St. George Street
- Touring the Old Jail
- The Old Town Trolley Tour
- Visiting Castillo de San Marcos
- Visiting Fort Matanzas
- Favorite Places to Eat in St. Augustine
- Parking in St. Augustine
- Walking Essentials for Exploring St. Augustine
- Things We’d Do Differently
- Final Thoughts
- More Florida Adventures
- Make the Most of Your Visit to St. Augustine
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Walking St. George Street
If you visit St. Augustine, chances are you’ll eventually end up on St. George Street. This pedestrian-only street is packed with historic buildings, restaurants, unique shops, and plenty of old Florida character.
The street has a relaxed atmosphere that makes it easy to spend hours exploring. One minute you’re checking out historic architecture, and the next you’re stepping into a small shop selling handmade candles, hot sauces, or local art.
There’s also no shortage of places to grab food or drinks along the way. From casual cafés to seafood restaurants and bakeries, you’ll definitely want to arrive hungry.
What we enjoy most about St. George Street is that it doesn’t feel overly rushed. Even with crowds, it still manages to feel laid back and walkable. The narrow brick streets and old buildings make you feel like you’ve stepped back in time.
For photographers, the area is full of opportunities. Early morning and late afternoon provide the best light for capturing the historic architecture without the harsh Florida midday sun.
Touring the Old Jail
One of the highlights of this trip was touring the Old Jail Museum, and honestly, it ended up being far more entertaining than we expected.
Built in 1891 by Henry Flagler, the jail operated for more than 60 years and housed some of St. Augustine’s most dangerous criminals. Today, it serves as both a museum and a guided tour attraction.
The tour guides fully lean into the experience and stay in character throughout much of the tour, mixing humor with the jail’s history. Between the storytelling, old jail cells, sheriff’s living quarters, and tales of past inmates, it made for a fun break from simply walking around town.
Some of the stories were surprisingly dark, while others had everyone in the group laughing. It struck a good balance between historical information and entertainment, which made it enjoyable even for visitors who normally aren’t big history buffs.
The jail itself is also very photogenic. The exterior architecture looks more like a hotel than a jail, which was apparently intentional because Henry Flagler didn’t want an ugly prison near his luxury hotels.
The Old Town Trolley Tour
On one of our earlier visits to St. Augustine, Lisa and I decided to take the Old Town Trolley Tours St. Augustine hop-on hop-off tour, and it turned out to be one of the best ways to explore the city.
St. Augustine has a lot of history packed into a relatively small area, and the trolley made it easy to move between attractions without constantly worrying about parking. Considering how busy downtown can get, especially during peak tourist season, that alone was worth it.
The trolley route covers many of the city’s major attractions, including the historic district, Castillo de San Marcos National Monument, the Old Jail Museum, and several museums and historic churches throughout town.
What really made the experience enjoyable were the trolley drivers. Most of them mixed local history with humor and storytelling, which kept the ride entertaining rather than feeling like a dry history lecture. We learned quite a bit about the city’s Spanish colonial roots, Henry Flagler’s impact on St. Augustine, and some of the local legends and ghost stories along the way.
The ability to hop off, spend time exploring an attraction, and then catch another trolley later made the entire day feel relaxed and flexible. It’s especially helpful if you’re visiting St. Augustine for the first time and want a good overview of the city before deciding where to spend more time.
If you only have a day or two in town, the trolley tour is honestly one of the easiest ways to maximize your visit.
Visiting Castillo de San Marcos
No trip to St. Augustine feels complete without visiting Castillo de San Marcos National Monument.
Originally constructed by the Spanish in the late 1600s, the fort is the oldest masonry fort in the continental United States. Sitting along Matanzas Bay, the massive coquina stone walls have survived centuries of attacks, wars, and hurricanes.
Walking through the fort is like stepping into a history book. You can explore the gun deck, look into the old rooms where soldiers once lived, and walk along the walls overlooking the water and downtown St. Augustine.
One of the most interesting things about the fort is the coquina stone used in construction. Made from compressed shell fragments, the material actually absorbed cannon fire better than traditional stone during attacks.
The views from the top of the fort are excellent, especially looking back toward downtown St. Augustine and out across the bay. If you enjoy photography, bring a wide-angle lens for the interior spaces and something with a little reach for details and waterfront shots.
Unfortunately, we just missed one of the cannon demonstrations during our visit, which was disappointing because the demonstrations are supposed to be one of the highlights of visiting the fort. Definitely check the schedule ahead of time if you plan to visit.
The National Park Service rangers dressed in period clothing really add to the experience and help bring the history of the fort to life. Watching the demonstrations with the historic uniforms, weapons, and explanations would make the visit even more memorable.
Visiting Fort Matanzas
During our previous visit, we also made the trip down to Fort Matanzas National Monument.
Fort Matanzas offers a very different experience compared to Castillo de San Marcos. Located south of town, the smaller fort is situated along the water and can be reached by a short ferry ride operated by the National Park Service.
The ferry ride alone makes the visit worthwhile. It’s a peaceful trip across the water, and once you arrive, you can explore the compact fort while learning how it helped protect the southern approach to St. Augustine.
Compared to the large and imposing Castillo de San Marcos, Fort Matanzas feels quieter and more isolated. Visiting both gives you a much better understanding of how the Spanish defended the area centuries ago.
Favorite Places to Eat in St. Augustine
One of the things we enjoy most about traveling is trying local restaurants, and St. Augustine didn’t disappoint. Here are three places we personally enjoyed during our visits.
Pizza Time
If you’re looking for a quick and satisfying meal while exploring St. George Street, Pizza Time is hard to beat. Known for its huge New York-style pizza slices, it’s a popular stop for both locals and visitors. The line can get long, but it’s worth the wait. We grabbed a slice while sightseeing, and it was the perfect lunch before continuing our walk through the Historic District.
Murray Bros. Caddyshack
We weren’t sure what to expect from Murray Bros. Caddyshack, but it turned out to be one of our favorite meals in St. Augustine. The golf-themed atmosphere is fun without being over the top, and the food exceeded our expectations.
Lisa ordered the Alfredo chicken, which was creamy, flavorful, and one of her favorite meals of the trip. I went with the blue cheese burger, and it was cooked perfectly with plenty of bold flavor. If you’re looking for a relaxing sit-down dinner after a day of sightseeing, this is a great choice.
Ford’s Garage
We also stopped at Ford’s Garage, a casual restaurant with a fun automotive theme inspired by classic Ford vehicles. The décor features vintage signs, antique gas pumps, and automotive memorabilia, making it an enjoyable place to look around while waiting for your food.
I ordered the Mushroom Swiss Burger, while Lisa chose the Crispy Chicken Sandwich. Both meals were good, with generous portions and quality ingredients, but they didn’t stand out quite as much as our dinner at Murray Bros. Caddyshack. Even so, if you’re looking for a casual lunch or dinner with a unique atmosphere, Ford’s Garage is a solid choice.
Parking in St. Augustine
Parking in downtown St. Augustine can definitely be a challenge, especially on weekends and during peak tourist season.
During our latest visit, we circled the parking lot at Castillo de San Marcos National Monument several times before finally finding an open spot. Once the city gets busy, parking fills up quickly.
If you visit during the week and arrive early in the morning, your chances of finding street parking are much better. We noticed many of the metered street parking spaces near the historic district were running about $2.50 per hour with a four-hour maximum stay.
Honestly, this is one reason we really liked using the Old Town Trolley Tours in St. Augustine during an earlier visit. It eliminated a lot of the stress of trying to move the vehicle around downtown and hunt for parking between attractions.
Walking Essentials for Exploring St. Augustine
St. Augustine is one of the most walkable cities we’ve visited. Between St. George Street, Castillo de San Marcos, the historic downtown, and the waterfront, you’ll likely spend hours on your feet. These are a few items we recommend bringing to stay comfortable throughout the day.
These are all items we regularly travel with and recommend for making the most of a day exploring America’s oldest city.
Things We’d Do Differently
Looking back on our visit, there are a couple of things we would absolutely do differently next time.
First, we would arrive much earlier in the day. Parking in downtown St. Augustine fills up fast, especially on weekends. By the time we arrived, we ended up circling the parking lot at Castillo de San Marcos National Monument multiple times before finally finding an open spot. Getting there earlier would have made the entire day a little less stressful and given us more time to explore before the crowds picked up.
The other thing we would definitely do is check the cannon demonstration schedule ahead of time. Unfortunately, we just missed one of the demonstrations during our visit. From everything we saw and heard, the demonstrations are one of the highlights of visiting Castillo de San Marcos.
The National Park Service rangers dressed in period clothing really help bring the fort’s history to life, and seeing the cannons fired with the historic demonstrations would have added even more to the experience. Next time, we’ll plan our day around the demonstration schedule instead of just hoping we arrive at the right time.
Final Thoughts
St. Augustine is one of those places we never seem to get tired of visiting. Between its history, waterfront scenery, walkable downtown area, and unique atmosphere, it’s easy to understand why so many people return again and again.
Whether you’re strolling along St. George Street, touring the Old Jail, riding the Old Town Trolley, exploring the massive walls of Castillo de San Marcos, or taking the ferry out to Fort Matanzas, there’s no shortage of things to experience in America’s oldest city.
If you’re traveling through northeast Florida, St. Augustine is absolutely worth adding to your itinerary. Just be prepared to do a lot of walking—and bring your camera.
More Florida Adventures
If you’re planning a Florida road trip, here are a few more places we’ve explored that are well worth adding to your itinerary:
- Visiting Gulf Islands National Seashore: Exploring Davis Bayou and Fort Barrancas – Discover scenic coastal trails, historic forts, and one of the most unique national parks in the country.
- National Naval Aviation Museum: Best Exhibits, Tips, and Must-See Aircraft – Explore one of the world’s premier aviation museums with legendary military aircraft, interactive exhibits, and free admission.
- Blue Angels Park – Blue Angels Recreation Area Campground Review – See why this military campground near Pensacola is one of our favorite places to stay, with waterfront campsites and easy access to the National Naval Aviation Museum and Pensacola Beach.
- Crab Island Explorer Tour: Is It Worth It? – Everything you need to know before visiting Destin’s famous sandbar, including what to expect, what to bring, and whether the tour is worth the money.
We’re always adding new Florida destinations, campground reviews, restaurants, and travel tips, so be sure to explore more of our Sunshine State adventures.
Make the Most of Your Visit to St. Augustine
Planning your trip? These are some of the top-rated experiences in St. Augustine that can help you make the most of your visit:
- Old Town Trolley Tour
- Sunset Cruise
- Dolphin & Wildlife Cruise
- Ghost Tour
- Historic Walking Tour
- St. Augustine Food Tour
What interesting places can you recommend?
We’re always on the lookout for unique, out-of-the-way experiences to add to our list.
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