St Augustine Itinerary: 3 Days in St Augustine Florida

Founded in 1565, St Augustine is America’s oldest city. It’s a great place to relax on vacation and take in some history. Because not only does St Augustine have a rich history, it also has an amazing food scene, art, and pristine beaches. This makes St. Augustine worth visiting for almost everyone – it’s a great destination for families, couples, friends – you name it. There can be so much to do that it can be hard to know what exactly to put in your St Augustine itinerary.

To make the most of your visit, and to make the planning easy, I have put together a St Augustine Itinerary for you. This St Augustine itinerary is for 3 days, but you could also adjust it to be a 2 day itinerary by taking off the beach activities on the third day or just by reorganizing the activities that feel best to you.

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How many days should I spend in St Augustine?

The first time we visited St Augustine was actually just for a day trip. Even though we left a lot left undiscovered, I felt like we got a good sense of what St Augustine had to offer in that trip. St Augustine is one of those destinations that really grabs ahold of you and makes you want to come back again and again.

With that being said, how many days to spend in St Augustine really depends on your style (and how much time you have). Are you the kind of traveler who likes to visit a place only once and cram absolutely everything you can into a day or two? In that case, you could see a lot of St Augustine in 2 days if you push yourself.

If you are more the type to see as much as you can, but slowly, taking it in without rushing then you could easily spend a week.

Like a lot of places, St Augustine has so much to do that even locals have things to do on their lists that they haven’t gotten to yet.

Main Highlights of your 3 Day St Augustine Itinerary:

Day One:
•Trolley tour, explore St George Street, Aviles Street, Ghost tour, good places to grab a drink
Day Two:
•Castillo de San Marcos, Fountain of Youth, historical buildings/museums (Flagler College, Lightner Museum, Old Jail), winery or distillery tour
Day Three:
• Have a beach day, climb the lighthouse, scenic boat ride

Day 1: Trolley, St George and Aviles Streets, Ghost Tour, Drinks

Start your first day in Saint Augustine with a coffee from Kookaburra. There are a lot of options for coffee in St Augustine but this was my favorite. It’s loved by both locals and visitors and there are a few locations throughout St Augustine, including at the beach.

Kookaburra serves Australian coffee (it does taste a little different, but in a good way) and Australian pies. My husband and I each ordered one of their specialty drinks and both were delicious. I also highly recommend getting a pie with your coffee. It is literally a small pie filled with whatever you order. They have breakfast pies and also different options for lunch.

Once you’ve grabbed your morning coffee, hop on the Old Town Trolley Tour. It’s a trolley that will take you to some of the best attractions and things to do in St Augustine. The trolley is the best way to see as much of St Augustine as possible in a short amount of time.

Every tour guide does it a little differently (I think that makes the tour more authentic, which I love) but the tour is around 90 minutes and you can jump off at any of the 22 stops that the trolley stops at. The trolley runs every 15 minutes so it’s easy to hop back on once you get off.

I recommend doing the full loop first to learn about everything then kind of deciding what your priorities are. Doing the full tour also helps you learn the physical location of each of these things as well. You might want to do some things not on my 3 day itinerary or you might decide some of the things on the St Augustine itinerary aren’t for you. By taking a trolley tour, you’re getting the lay of the land and getting familiar with your surroundings to make the most of your time in St Augustine.

Eat lunch at The Floridian or Florida Cracker Cafe. At the end of this article, I listed some of the most popular restaurants in St Augustine with a bit more of a description if you’d like some more information.

On the afternoon of your first day in St Augustine, I recommend exploring St George Street. It’s a pedestrian only street in St Augustine bustling with shops, restaurants, and more. It’s a fun, busy street. I recommend wandering the entirety of the street, but some of my favorite places to stop are:

• Old City Gates were built in 1808! St. Augustine residents built the structure entirely out of coquina (a rare form of limestone composed of the shell fragments – I recommend looking up close because you can see the shell fragments, which is really cool!). The gates were used for access into the city as well as protection for people living there at the time.
• Oldest Wooden Schoolhouse has been around since the early 1700s. You can tour this small building, which is very interesting. It is the oldest wooden school building in the United States!
• Whetstone Chocolates – Not only are the chocolates delicious but you can take a tour, which I recommend if you have the time.
• Finding live music! There is a lot of live music around St Augustine, you’ll come by it naturally just by wandering the streets

How much time you’ll spend exploring St George Street will depend on what you’re looking for and your style. If you like to take your time and go into a lot of places or if you want to grab drinks as you go, it could easily take all day. If you’re just walking down the street as fast as you can just to say you’ve seen it, it can take under an hour.

I also recommend exploring Aviles Street if you have time. It is the oldest street in St Augustine and is just one street over from St. George Street. And just like St George Street, it has shops, restaurants, and museums. Back in the day, it was known as the hospital street because the Spanish Military Hospital was located there. Today it’s known as the art district.

For dinner, try OC Whites. It’s an American grill with plenty of seafood options and I recommend sitting in the courtyard.

End the your first day with a Ghost Tour. St Augustine is one of the most haunted cities in America and this tour will teach you all about the stories behind some of St Augustine’s most haunted places. Even if you aren’t into the whole haunted thing, it’s a really fun way to learn more about some of the events that have happened in St Augustine.

If you’re into grabbing drinks, St Augustine has no shortage of great places to grab one. Here are some of my favorite places to grab a drink in St Augustine:

• Tipsy Duck Parlor: a rubber duck themed cocktail bar; every drink comes with a duck!
• The Tini Martini Bar: a wide variety of amazing martinis
• St George Tavern: Oldest bar in St Augustine
• Ice Plant Bar: Unique and seasonal cocktails, located in a 1927 industrial building
• River and Fort: Has a rooftop bar with views of the bay and Bridge of Lions, there is also a restaurant downstairs
• All of the breweries are good – Ancient City Taproom, Old Coast Ales (located across the Bridge of Lions from downtown St Augustine – the taco shop next door is amazing as well), Bog Brewing Company (a little out of the way from downtown St Augustine), and Dog Rose Brewing Company.

Day 2: History in St Augustine

Start your morning with coffee from Crucial Coffee Cafe. This is the cutest coffee shop in St Augustine and located right across the street from the Castillo de San Marcos.

On the second day of your St Augustine itinerary, you’ll be diving into history.

The first stop is a must visit, Castillo de San Marcos. This is one of the top attractions in St Augustine. It’s a fort that was built by the Spanish between 1672 and 1695 to defend their Florida territory. It’s the oldest surviving masonry fortress of its kind. The fort was built with coquina (soft limestone made of broken shells) just like the Old City Gates. And just like the Old City Gates, if you look at the walls, you can actually see the tiny shells that are crushed together.

Through the years, the Castillo has never been captured in battle. It has traded ownership over the centuries. Canons are fired from the gun deck on the weekends. The canons are fired most Saturdays and Sundays at 10:30, 11:30, 1:30, 2:30, and 3:30. 

Visit the Fountain of Youth Archaeological Park. The Fountain of Youth is a spring rumored to restore the youth of anyone who drinks or bathes in its waters. You won’t be able to bathe in the spring while you’re there, but you can drink some of the water. It tasted a lot like the water I used to drink out of a hose as a kid.

Something that I didn’t know about the Fountain of Youth before visiting is that there is actually a lot more to do than just visit the spring. It is located in the same place as America’s First Colony exhibit. There are tons of exhibits to learn about more of the history of St Augustine. We enjoyed learning more about the Timucuan, one of the largest groups of Native Americans in Florida. We had only planned for a short amount of time here, not knowing there was so much to do, but could have easily spent several hours.

Lunch: Grab BBQ from Mojos BBQ (their homemade BBQ sauces are so good) or Spanish/Mexican food from Casa Reina (if you can get outdoor seating, you’ll have a view of the marina and the famous Bridge of Lions). Or, if you’re a foodie jump on a Culinary Tour.

Spend your afternoon exploring one or more of St Augustine’s historic buildings or museums. Given that St Augustine is such a historic city, you won’t be able to explore all of its history in 2-3 days unless you’re really rushing. So you’ll probably have to choose between some of your options.

• Flagler College Historic Tours: Flagler College was built by Henry Flagler in 1888 (a businessman who started a successful oil company and also the man responsible for the Overseas Highway to the Florida Keys). Flager College was originally Hotel Ponce de Leon, a luxury hotel where the wealthy enjoyed staying. The hotel was famous and its most notable guests included Teddy Roosevelt, Mark Twain, and Andrew Carnegie. If you want a tour, they run 2-3 times per day but even if you don’t want to go on an official tour, it’s worth walking around the campus. It is stunning!
• Lightner Museum (located right by the Flagler College, making it easy to do both): Has a great art collection, mostly from the 19th century, and also has Tiffany stained glass, an American Cut Glass Gallery (this was my favorite part), Gilded Age furniture, and a collection of hobbies and curiosities from the founder, Otto Lightner. The building itself is impressive as well; it was once the Hotel Alcazar. Today, you can eat lunch in what was once the hotel’s pool.
• Old Jail Museum & Oldest Store Museum (located in the same place): The Old Jail Museum will teach you about the history of some of St Augustine’s most notorious criminals as well as the conditions they endured there. The jail is one of St Augustines most haunted places. The Oldest Store Museum recreates a general store from 1908.
• Medieval Torture Museum – we visited this museum on our first trip. We hadn’t heard about the museum before we visited so we had no expectations but it’s been over 5 years and we still talk about how cool this museum is. The museum covers different ways people have been tortured in the past. It’s probably not for kids depending on their age. It’s fascinating (and a little disturbing)!
• St. Augustine Pirate Treasure & Museum to learn all about pirates, see recovered treasure, and more. It is a smaller museum that takes around one hour to visit.

After you explore St Augustine’s history, take a wine tour at the San Sebastian Winery or a distillery tour at the St Augustine Distillery.

Grab dinner at Harrys (New Orleans inspired seafood) or OC Whites (upscale Peruvian restaurant).

Day 3: St Augustine Lighthouse & Beach

Start your morning with donuts from Island Donuts. Or, if you are visiting on a Saturday, head to the amphitheater for the Farmer’s Market. The Farmer’s Market is from 8:30 – 12:30 and there is plenty of local food, fresh food, produce, arts and crafts, and more. There is also live entertainment!

Have a beach day! The beach is not in walking distance from the downtown area of St Augustine. But if you want a beach day, St Augustine is a great place to do it – the Atlantic Ocean is beautiful and has more waves than Florida’s Gulf Coast beaches. You can also visit the St Augustine Beach Pier (there is parking there) or head to Anastasia State Park Beach, which has a small entrance fee. The state park also has trails and kayak rentals.

Note: We prefer to stay in the Downtown St Augustine area when we visit. But if you prefer to stay at the beach and drive into downtown when you want to explore there, then there are some good lodging options. Guy Harvey Resort St Augustine Beach and Embassy Suites by Hilton at St Augustine Beach are both good options.

Explore the St Augustine Lighthouse. The lighthouse is located on the north end of Anastasia Island, so you’ll be able to get good views of St. Augustine, the bay, and the beach. If you have kids, know that if they are under 44″, they cannot climb to the top of the lighthouse. The lighthouse is 165 feet tall and there are 219 steps to the top. You can also see the keeper’s house on the property as well as some other exhibits and a nature trail. The St Augustine Lighthouse is believed to be haunted.

See a different view of St Augustine on a scenic boat ride. Similarly, you can also book a sunset cruise. With both options, the captain will fill you in on some of St Augustine’s history. You’ll get a unique view of many St Augustine landmarks from the water, such as the Bridge of Lions, Castillo de San Marcos, and more. You also might get lucky and see some dolphins.

Have dinner at Osteens, a laid back restaurant that is famous for their shrimp. They are not open Sunday or Monday.

If you have extra time

If you have more than a couple days in St Augustine, here are some more amazing things to do there. You may also want to browse this list to see if anything sounds more interesting than some of the ideas above, you can always swap them out!

The Alligator Farm is a great stop, especially if you have kids. You can learn all about alligators and, of course, see tons of them (they have 24 species there). They even have a zip line if you’d like to zip line over the top of them. While alligators and crocodiles are the biggest draw, there are also other reptiles and birds there. They list all of the species they have on their website.

Churches of St Augustine. St Augustine has several amazing churches. First, the Flagler Memorial Presbyterian Church is worth a visit because this is where Henry Flagler is buried (as well as his daughter and first wife). The Ancient City Baptist Church, Cathedral Basilica of St Augustine, and Grace United Methodist Church are worth visiting for their gorgeous buildings and stained glass windows.

The Huguenot and Tolomato Cemeteries can be visited on the third Saturday of each month (you can only go inside the cemeteries on this day). The Tolomato Cemetery is the oldest Cemetery in St Augustine.

When Should I Visit St Augustine?

The best time to visit St Augustine will depend on what you are looking for. If you’re coming for the beach, then summer will be a good time to visit. Summers are hot and perfect for cooling off in the water.

If you’re like me and prefer to dodge the peak crowds while still catching some glorious beach days, aim for May. The weather is good in May because it’s hot enough to enjoy the beach but it isn’t too hot yet. In May, it usually isn’t too crowded because kids are still in school and the snowbirds have usually gone back home. Just be aware of Memorial Day because it will be packed that weekend. September and early October also tend to be similar in terms of weather and crowds.

If your St. Augustine adventure isn’t centered around beach lounging, March to May and September to October tend to be sweet spots. The weather is great and the crowds are noticeably thinner. Though keep in mind, it may still be crowded because St Augustine is a popular vacation destination no matter the time of year.

St Augustine is one of the best Florida cities to celebrate the holidays, mostly because of Nights of Lights. Basically, Nights of Lights is a ton of Christmas lights all around town, literally 3 million+ lights! It’s very magical and the event runs from the end of November through the end of January. This event attracts people from all over and it tends to be very busy, especially on the weekends and close to Christmas. We went in late January to see the lights thinking it wouldn’t be busy so late in the season. And even though it wasn’t as busy as it tends to be in December, it was still really crowded.

Best Place to Stay in St Augustine

There are plenty of Airbnbs in St Augustine. Our personal preference is to stay within walking distance to the downtown area. If you plan on this being primarily a beach vacation, you might prefer staying at the beach. Just keep in mind that you will likely want a car to get back and forth between the beach and downtown St Augustine.

On our last visit, we stayed just across the Bridge of Lions. This is in walking distance to the downtown area, and you’ll see people walking over the bridge throughout the day. But if you’re like us, you’ll be doing a lot of walking throughout the day and adding the walk over the bridge on top of the several miles we were doing all day wasn’t ideal for us.

So with that being said, I’d recommend Casa Monica Resort & Spa. It has a perfect location next to the Lightner Museum and is right on the edge of all the action of downtown St Augustine. It’s a gorgeous hotel, built in 1888.

The Hilton St Augustine Historic Bayfront is another great option. Some rooms have water views of the bay and it’s also in a great area of town. It’s just across the street of the Castillo de San Marcos.

Events in St Augustine

St Augustine has a ton of events throughout the year. If you happen to be visiting during any of these events, they are worth a visit. Some events, like Nights of Lights, are even big enough for visitors to plan their entire vacation around.

• First Friday Art Walk – First Friday of every month from 5-9 pm
• Music by the Sea – Live concert every Wednesday 7pm – 9 pm from May through September
• Concerts at the Plaza – Free Thursday night concert from 6pm – 8 pm. May through September.

January

• Jimmy Jam BBQ Slam & Car Show – a BBQ competition with classic cars. There are also arts and crafts and live music.
• St Augustine Film Festival
• Matanzas 5K run

February

• Flight to Freedom – recreates the experience of the hundreds of slaves who traveled to Fort Mose for freedom
• Fort Mose Jazz and Blues Series
• St Augustine Spanish Food and Wine Festival

March

• St Augustine Celtic Music & Heritage Festival
• The Players Golf Championship
• Blessing of the Fleet – watercraft of all kinds are decorated to receive a blessing from the Bishop of the Diocese of St Augustine
• St Augustine Easter Parade

April

• St Augustine Lions Seafood Festival
• Songwriters Festival
• Birding and Photo Fest

May

• Latin American Festival
• Food and Wine Festival
• Craft Brewer’s Fest
• Drake’s Rade – recreation of 1586 attack on the city

June

• Music Festival
• Battle of Bloody Mose – reenactment of the battle that occurred June 1740

July

• Fourth of July – live music and fireworks at the plaza
• Kingfish Challenge – huge fishing tournament

September

• City of St. Augustine Birthday Celebration
• Sing Out Loud Festival – one of the largest free music festivals in Florida

October

• Greek Festival

November

• Nights of Lights – 3 million + Christmas lights throughout town, goes from mid November through the end of January

December

• St Augustine Christmas Parade
• Garden Club Christmas Tour of Homes
• St Augustine Boat Parade
• Nights of Lights
• New Years Eve firework show

Restaurants in St Augustine

I listed some of my favorite meal options in each day’s itinerary, but here is my list of popular places to eat in St Augustine:

• The Blue Hen Cafe – Great breakfast spot with a unique take on breakfast staples – try their blue crab quiche or BBQ pulled pork & grits. It’s also popular so you’ll want to get there early.
• The Floridian – Modern menu of locally sourced Southern food
• Florida Cracker Cafe – Seafood shack located right on St George Street
• Harry’s Seafood Bar and Grille: Cajun Seafood known for great fish tacos
• Prohibition Kitchen: American restaurant and bar located in the Historic Center. 
• Columbia Restaurant: Popular Spanish restaurant in the heart of Downtown. In full disclosure, we have not eaten at the location in St Augustine but we have eaten at their flagship restaurant in Tampa. I highly recommend the 1905 salad.
• OC Whites – Seafood restaurant located in a historic home
• Mojos – Really good BBQ
• Casa Reina – Spanish/Mexican food, very popular so there can be a long wait
• Osteens – famous for their shrimp (located across the Bridge of Lions from downtown St Augustine)
• Mayday Ice Cream Historic St. Augustine in case you need an ice cream fix, they are located right on St. George St. 
• Llama – fine dining serving Peruvian food

Do I need a car to get around St Augustine?

You will probably be flying into the Jacksonville airport (JAX). St Augustine is around an hour from the airport.

If you plan on only staying around the downtown area, then pretty much everything is walkable (or you can take the trolley to save time). But if you want to go to the beach, you might want to rent a car. Especially if you want to visit the beach multiple times (or if you are doing it the other way around and are staying at the beach but visiting downtown).

We have always needed to drive on our trips to St Augustine and we haven’t had issues finding parking downtown. However, we have always arrived early and every time we’ve left, the lots are pretty full. I recommend arriving early, especially if you’re visiting during a holiday or busy season. You can find free parking at The Old Jail.

From the ancient walls of the Castillo de San Marcos to the gorgeous beaches of St Augustine Beach, there are many activities in St Augustine to make your trip memorable. As you plan your journey, I hope that this itinerary has been helpful for your trip to Florida’s historic coast.