Perfect Weekend in St. Augustine Itinerary  

St. Augustine, Florida, is a great city for a short trip like a weekend getaway. There are endless options for how to spend your time here. With this weekend in St. Augustine itinerary, you can have the perfect visit to America’s oldest city. 

In fact, there are so many things to do in St. Augustine you’ll have trouble narrowing it down to what you can reasonably manage to do in one weekend. Whether you crave adventure or relaxation, there are endless options for how to spend your time here! 

Flag and cannons on the top of Castillo de San Marcos National Monument
A weekend in St. Augustine makes a great getaway. Photo: Plan, Ready, Go.

Need help planning your St. Augustine weekend getaway? Then don’t miss our essential travel planning resources page.  

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How many days do you need in St. Augustine? 

Although it would take you quite a while to see everything in St. Augustine, we recommend a visit of two to three days to see the top sites and attractions. We love how compact the historic area of St. Augustine is, making it easy to see a lot in a short amount of time. It’s perfect for a weekend getaway

You can easily plan a trip to St. Augustine, Florida, with this weekend itinerary. We’ve covered the top sites. But don’t worry, we’ve also provided some recommendations for other things to do as well so that you can customize your itinerary. 

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St. Augustine Weekend Itinerary: Day 1 

Explore Castillo de San Marcos National Monument 

View of Castillo de San Marcos from Colonial Quarter Watchtower in St. Augustine, Florida
Make sure your St. Augustine itinerary includes a stop at Castillo de San Marcos National Monument: Photo: Plan, Ready, Go.

Address: 1 South Castillo Drive, Saint Augustine, FL 32084 

I recommend you start your trip with a visit to Castillo de San Marcos National Monument. It’s one of the most visited sites in St. Augustine and for good reason. 

It’s the oldest masonry fortification in the U.S., and (supposedly) one of only two existing structures in the world built from coquina. Coquina is composed of shell fragments and sand, which makes it ideal for military fort construction. 

Unlike other forms of stone that would shatter when struck by cannon fire, because coquina is quite porous it simply compressed. So, it would actually deflect the shot or cannon balls would even lodge within the fortress walls. 

We recommend you do the fort first thing in the morning. Later in the morning, there can be a long line to enter. And of course, in the summer months, the interior of the Castillo can get quite hot.  

While there is a fee to enter the fort, guests are welcome to stroll the grounds outside for free. You can also use your America the Beautiful pass for entry. 

Paid parking is available nearby at the adjacent parking lot or in the city parking garage just a few blocks away.  

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Check out historic St. George Street 

Just a short stroll away from Castillo de San Marcos is historic St. George Street. St. George Street is the main street that runs down the center of old St. Augustine. The street is closed to vehicles and home to many points of interest in the city such as museums, restaurants, and shops. 

Have fun looking through everything this street has to offer. And don’t miss poking around the little side streets too. 

Ponce de Leon’s Fountain of Youth Archeological Park 

Statue of Ponce de Leon at Fountain of Youth Archeological Park in Florida
The Fountain of Youth Archeological Park marks the original site of St. Augustine. Photo: Plan, Ready, Go.

Address: 11 Magnolia Avenue, St. Augustine, FL USA, 32084 

For this site, you’ll have to hop in your car and head just a few minutes outside of central St. Augustine. The  Archeological Park marks the location of the native Timuacan village of Seloy. It was also the original location of St. Augustine. 

Much like Historic Jamestowne, you can visit sites in the park that mark locations of original buildings. 

filling a cup of water at the Fountain of Youth
Catching some water from the “fountain of youth.” Photo: Plan, Ready, Go.

The Park is also part living history museum with firearms and blacksmithing demonstrations. 

You can get a small discount if you purchase tickets in advance online or you can buy at the ticket office on site. There are no same-day ticket sales online. 

Make sure to stop at the Fountain House to try a sip of the water from the “Fountain of Youth.” This is just for fun. There doesn’t appear to be any archeological evidence that Ponce de Leon ever set foot anywhere in the area of this park. 

Featured tours in St. Augustine 

If you’re looking for other activities to add to your St. Augustine weekend itinerary, check out these featured tours. All have free cancellation available. 

This trolley tour is quite popular and provides an overview of St. Augustine.  

Or explore St. Augustine with a private electric cart tour.

Or why not try a spooky ghost tour one evening? 

St. Augustine Weekend Itinerary: Day 2 

Take a Colonial Quarter tour 

old printing press inside an old wooden building at the Colonial Quarter
Touring the Colonial Quarter is a popular thing to do in St. Augustine. Photo: Plan, Ready, Go.

Purchase tickets at 14 S. Castillo Drive 

The Colonial Quarter living history museum should definitely be on your St. Augustine weekend itinerary.  

If you’ve ever been to Colonial Williamsburg, then you definitely have an idea of what Colonial Quarter is like…just on a much larger scale. Your Colonial Quarter ticket includes a guided tour of the museum.

Our tour guide, Bert, was outstanding. He walked us through hundreds of years of St. Augustine history, as the oldest permanent European settlement in North America. 

The tour includes live demonstrations of blacksmithing and firearms, plus you can walk through a historic house and climb the watchtower for a great view of Castillo de San Marcos and the Matanzas River. 

Stroll the oldest street in America 

old narrow cobblestone street in St Augustine Florida
Aviles Street. Photo: Plan, Ready, Go.

As long as you’re in the oldest city in America, why not also take a walk along the oldest street in America while you’re there? Aviles Street is located south of Plaza de la Constitución between St. George Street and Charlotte Street

In addition to making a great photo spot, Aviles Street is also home to art galleries, museums, and restaurants. 

Pirate & Treasure Museum 

Exterior of Pirate & Treasure Museum and sign

Location: 12 South Castillo Drive, St. Augustine, FL 32084 

I recommend you make a stop at the Pirate & Treasure Museum during your St. Augustine weekend getaway. 

Initially, I visited the museum almost solely out of curiosity, but I was so glad I went. It’s not a large museum, but the exhibits are well done, fun, and engaging. There is an impressive collection of historical pirate artifacts in the museum including a “treasure chest” and an old Jolly Roger flag. 

The Pirate & Treasure Museum is a little dark (in every sense of the word) and might not be appropriate for very young children. The museum was established by pirate history enthusiast and entrepreneur Pat Croce. It was originally located in Key West, Florida, and then moved to St. Augustine. 

You can purchase tickets in the museum or buy them ahead of time online

Oldest Wooden School House 

Oldest Wooden Schoolhouse building exterior
The Oldest Wooden School House is a fun and quick stop. Photo: Plan, Ready, Go.

Okay, this one’s mainly just for a laugh. If you have time (and a little money to spare) I recommend you consider popping into the Oldest Wooden Schoolhouse. You’ll find it at the top of St. George Street. 

It’s quite small, so it won’t take much time at all to see every square inch of it. It’s also…how do I put this delicately?…so cheesy and hokey and cringe-y. 

When we were there it was full of creepy mannequins. They stared at us from everywhere. There was even a child mannequin stashed UNDER THE STAIRS as “punishment.”

It was highly entertaining, but we kept our amusement to ourselves since those who sold us our tickets seemed to take it all very seriously and we didn’t want to insult them. 

More things to do in St. Augustine 

View of the stage at the St. Augustine Amphitheater
We snagged tickets to the sold-out Beach Boys concert during our St. Augustine getaway. Photo: Plan, Ready, Go.

Of course, there’s much more to do in St. Augustine than you can fit into one weekend. 

If you enjoy music, definitely take a look at what’s going on at the St. Augustine Amphitheater during your visit. It’s a great venue and just a short drive from the historic center of the city on Anastasia Island. Anastasia makes a great day trip from St. Augustine. 

Check out these additional options. All include free 24-hour cancellation. 

Where to stay in St. Augustine 

Although its historic center is quite compact there is no shortage of accommodations. You’ll find a wide variety of places to stay from vacation rentals to small B&Bs and boutique hotels. 

Affordable major chain hotels are also nearby and make a good budget option. 

A vacation rental just steps from the historic district like this one on Airbnb has plenty of room for a small family or it’s perfect for a couple. And since it includes a full kitchen, it’s easy to save money on food by cooking your own meals instead of eating out. 

If you’re interested in hotel accommodations here are some top-rated and recommended options: 

Casa Monica: This iconic resort and spa in the historic district is a popular high-end place to stay. It’s located very near Plaza de la Constitución. Book your stay right now.  

Penny Farthing Inn: This Bed & Breakfast is located in historic St. Augustine near the popular Lightner Museum. Book your stay today

Where to Eat in St. Augustine 

Of course, if you stay at a Vrbo or Airbnb, you can save money on food by eating in. 

You can shop for food and supplies at the local Publix (125 Jenkins St, St. Augustine, FL 32086) or the Target at 1440 US Hwy 1 S, St. Augustine, FL 32084. 

If you do want to eat out, here are a few places we would recommend for lunch or dinner: 

The Floridian 

Location: 72 Spanish St #3638, St. Augustine, FL 32084 

We highly recommend you make time for dinner at The Floridian during your St. Augustine weekend. We thought the food and service were outstanding. They have great vegetarian and gluten-free options.  

It’s a popular spot, so reservations are recommended. Check out their menus here

Large white bowl willed with golden curry and rice on a wooden table
Dinner at The Floridian was a highlight of our trip to St. Augustine. Photo: Plan. Ready, Go.


Location: 98 St George St, St. Augustine, FL 32084 

My husband’s favorite meal of our St. Augustine visit was at Columbia. They have some great gluten-free options and some solid vegetarian options. Hubby claims Columbia has the best flan he’s ever tasted. 

This is not an inexpensive restaurant, but you can save a little money if you eat there for lunch. Reservations are strongly recommended

Sweet treats 

There are also great places in St. Augustine to get snacks and dessert: 

Belgian waffle with whipped cream dusted with powdered in a paper container
A hot Belgian waffle from Cousteau’s makes a great treat after a day of walking through St. Augustine. Photo: Plan, Ready, Go.

Tips for visiting St. Augustine 

When to go 

You’ll enjoy smaller crowds and somewhat lower temperatures if you visit St. Augustine between October and April. The rainiest months on average are from June through September, where it can rain up to 10 or 11 days out of the month. 

How to get around 

The best way to get around historic St. Augustine for your day trip is to use your feet. The historic district is quite compact with most top sites very close to each other.  

If you’re staying outside the historic area of St. Augustine, you can park your car in the Historic Downtown Parking Facility (1 Cordova Street) and then easily walk to nearly everything you want to see.  

There may be some limited street parking around the area, but we would recommend you use the garage. There’s also a convenient Visitor Center there, as well as restrooms and a gift shop. 

The bottom line

If you’re looking for a beautiful destination with a rich history, then St. Augustine is the place to be. Whether you enjoy history, food, or outdoor adventure, you can’t go wrong with a St. Augustine weekend getaway. 

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  1. Monica Pena says:

    Wow! thank you so much for this post. Will definitely save it. We’re planning on going for our honeymoon 🙂

    1. Darcy Vierow says:

      Wonderful! I think you’ll really enjoy it. And congratulations!

  2. Isn’t St. Augustine home to the oldest Catholic church and Mass celebrated in North America? I am surprised this is not mentioned in your article, even to non-Christians, as a very significant historical event.

    1. Darcy Vierow says:

      The Cathedral of San Juan in Puerto Rico is older, but it would be good to mention the Cathedral Basilica of St. Augustine.

  3. Recommend a tour of Flagler College as well. The history of the main building and the architecture of the historic Ponce de Leon Hotel is amazing.

    1. Darcy Vierow says:

      Yes! Good suggestion. I’ve heard only good things. Unfortunately, they were closed for tours when I was in town.

  4. Hi. Quick note: It’s the Lightner Museaum. Not Leitner.

    1. Darcy Vierow says:

      Oof. Thanks for catching my embarrassing spelling error. It’s fixed now.

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