Weekend in St. Augustine: Perfect 2 or 3 Day Itinerary

As you may know, St. Augustine is the oldest continually inhabited city in the United States, which makes it a historically important city. While history class may have made you yawn as a student, you’ll find that there’s nothing boring about St. Augustine! It’s a quaint city with a lot of charm. In order to ensure that you have a fabulous time in St. Augustine, I have put together the perfect 3 day itinerary! This itinerary will make sure you see the best of everything St. Augustine has to offer! So, let’s get started!

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St. Augustine Itinerary – Day 1

Take a Tour of Flagler College

Flagler College free things to do in st augustine itinerary

Flagler College is spread out over multiple buildings, many of which were built by Henry Flagler. The tour focuses on Ponce Hall, which used to be the main building for Flagler’s Ponce de Leon Hotel. In its day, the hotel was the pinnacle of luxury, which was reflected in every aspect of the architecture. On the tour, you will get to see Henry Flagler’s attention to detail in every room.

Explore the Castillo de San Marco

Castillo de San Marco best time to visit st augustine florida

This is the fort that the Spanish built shortly after settling in St. Augustine. The fort is made from coquina, which you will learn a lot about while in St. Augustine–it was the Spanish setteler’s favorite building material in St. Augustine. Perhaps one of the coolest parts about this fort is that it saw battle many years and you can still see evidence of that today!
This doesn’t mean that the fort is crumbling–it’s actually in fantastic shape. It means that you can see impressions of cannonballs on the side of the fort! Yeah, seriously.
In addition to seeing inside, make sure you take a walk around the fort so you can see them! Also, the fort does scheduled cannon firings on the weekend, which is always fun to see!

Learn more about the Castillo de San Marco here.

Walk Down St. George Street

St. George Street is likely the most popular street in all of St. Augustine. It is a street lined with shops and restaurants and ice cream parlors. If you’re interested in finding a souvenir, this is where you’ll want to shop. You can find almost anything on St. George Street. It’s also a great place to grab a bite to eat for lunch or dinner. There are many awesome, small restaurants, and a few nice restaurants as well. (I’ll give you specific recommendations below!) While exploring St. George Street, you should stop by one of the many sweet shops and grab a treat! You can find gelato, ice cream, fudge, coffee, Dole Whip (yeah, you read that correctly!), popsicles, and so much more.

Get a Photo at the Original City Gate

City Gates 2 or 3 days in st augustine florida itinerary

At the north end of St. George Street, you will find St. Augustine’s original city gates! Definitely don’t leave without grabbing a photo of you and your family/friends at this historical site!

Take a Ghost Tour

Because of St. Augustine’s history, the city is rumored to be haunted! So, of course, you absolutely must go on a ghost tour!

There are a two types: walking tours and trolley tours. On a walking tour, the tour guide will lead you to multiple haunted spots around the city, give you some history (which usually ties in with why it’s supposedly haunted), and then essentially tells you a ghost story. The trolley tours are similar to a walking tour except that you get to ride instead of walk. Personally, I thoroughly enjoyed the walking ghost tour I took of St. Augustine. There was a great balance of history and ghost stories. Plus, it was interactive because you could actually converse with your guide and try and capture ghosts with your camera, which is difficult to do on a moving trolley.

Just know that there is a ghost tour for everyone!


St. Augustine Itinerary – Day 2

Go to the Beach

Can you honestly vacation in Florida without going to the beach? I didn’t think so!

St. Augustine has multiple lovely beaches just a short drive away from the historic district. So jump in your car or order an Uber! If you’re visiting during a warm time of year, definitely visit the beach in the morning! Grab a towel and lay out on the sand and soak up the sun! If you plan on getting in the water, make sure you’re paying attention to the flags!

However, if it’s winter, you might want to take a walk along the beach in the afternoon instead.

You can visit Vilano Beach, Crescent Beach, or Anastasia State Park.

Climb the St. Augustine Lighthouse

The St. Augustine Lighthouse is located on Anastasia Island, which is just a short drive away from St. Augustine’s historic district. The lighthouse has a lot of history, which you can learn about at the museum and on the tour! Then, you can climb to the top of the lighthouse for a spectacular view!

Learn more about the St. Augustine Lighthouse here.

(If you are traveling with children, you might want to skip the next 2 suggestions unless you have a sitter. Instead check out this guide to traveling to St. Augustine with kids.)

Tour San Sebastian Winery and Taste the Wine (For Free!)

San Sebastian Winery weekend in st augustine itinerary travel blog

You probably don’t think of Florida when you think of wine. However, you may begin to think differently after you taste the wine at San Sebastian Winery! I recently took a tour and fell in love with two of their wines: Vinter’s Red and Rosa. The tour is surprisingly informative. If you don’t know much about how wine is made, you will definitely know after the tour!

Enjoy the Nightlife

St. Augustine is full of college students and tourists, so there are tons of fun, bustling bars! You can grab a cheap bear at Scarlet O’Hara’s, or you can spend your time in a modern cocktail bar, such as Odd Birds Bar. The possibilities are nearly endless! I definitely recommend using google maps to pick a few bars that look particularly interesting to you, and stopping by each for a drink! This way, you’ll get to experience the best of St. Augustine’s nightlife! No matter where you go, you’re sure to have a great time!

St. Augustine Itinerary – Day 3

Visit the Alligator Farm

You can’t visit Florida without seeing some alligators! Spend a few hours learning all about the different species of alligator and seeing real live gators! Plus, you can even watch a caretaker feed them. It’s pretty awesome! You can easily spend at least half of a day at the Alligator Farm, so make sure you wear sunscreen!

Learn more about the Alligator Farm and read reviews here.

Take a Sunset Cruise

After a long (but fun!) day at the Alligator Farm, you should take a relaxing sunset cruise. On board, you’ll have the opportunity to see some beautiful views and take some awesome pictures!
You have a lot of different options when it comes to choosing a sunset cruise. You can take an adult only cruise or a kid-friendly cruise. It’s really up to you!

Don’t forget to check groupon because they often have awesome deals on a few sunset cruises! (Just make sure you read the fine print!)

Where to Stay in St. Augustine

Casa Monica Resort & Spa

Casa Monica best places to stay in St Augustine Florida

This hotel can be a bit pricey, but it’s definitely worth it! You will be in the heart of the historic district, and you’ll be staying in a luxurious, historic building. With top-notch guest services, you will feel like royalty. In fact, the King of Spain stayed there during St. Augustine’s 450th year celebration a few years back! So, if it’s good enough for the King of Spain, I think you’ll love it!

Click here to see latest prices and click here to read reviews here.

Bed & Breakfast

Okay, so if the Casa Monica isn’t quite your speed, you should definitely stay at a Bed & Breakfast! There are plenty of them located in and within walking distance of the historic district of St. Augustine. However, during popular times, they all book up quickly, so make sure you plan your trip in advance.

Bed & Breakfasts are fantastic because they are just as cozy and cute as the city of St. Augustine, which makes them compliment each other nicely!

Plus, Bed & Breakfasts are a lot more personal than hotels, so you’ll likely get to know the owners and other guests, which can greatly improve your experience in St. Augustine.


Where to Eat in St. Augustine

Ah, it’s the moment you’ve been waiting for: we’re going to talk about food!

Counter-Service Restaurants

Burrito Works Taco Shop

It’s a little hole in the wall Taco Shop, so be careful, you might walk right by it. They serve great food, and they make it there right in front of you, which is always nice! This restaurant is located right on St. George Street, which makes it conveniently located! The one downside to Burrito Works Taco Shop is that there’s not much seating, so when it’s busy, you might have a difficult time finding a seat.

Pizza Time

Pizza Time is located on St. George Street and serves great pizza by the slice! They are highly rated by visitors, which is why they have a line out the door during meal times. Don’t fret though! A line out the door doesn’t mean it’s that long considering the ordering process will start as soon as you walk in. I personally didn’t like that I was asked what I wanted right when I walked in because I wasn’t able to see all of my options. (The pizza you can choose from are spread out on the counter.) So, I just ordered something. However, once I tasted the pizza, I quickly got over it. If you visit Pizza Time, just remember to bring cash as they don’t take credit cards.

Pizza Time is another destination where you might have trouble finding a place to sit. Unfortunately, the shop sizes on St. George Street can be pretty small, and two of the most popular spots just so happen to have really small spaces.

Table-Service Restaurants

Prohibition Kitchen

This restaurant doesn’t have a dress code or anything like that. The only reasons it’s in this category is because it’s table service and a bit pricey. However, the food and atmosphere is incredible. If you don’t want to spend money on dinner here, you should at least stop by for a drink at the bar! They did such a great job with the decorations and the ambiance. Plus, they frequently have live music!

The Columbia

The Columbia serves traditional Spanish food, and it is amazing! Seriously, you need to order your favorite Spanish dish (or try something new!) and order a glass (or a pitcher) of sangria.
The atmosphere is cozy but fancy. Feel free to get dressed up! However, they’ll let you eat in your shorts too!

The Floridian

The Floridian serves an interesting collection of fantastic dishes. I have eaten there multiple times and have loved everything I’ve tried! Although, I will admit that their menu can be a little intimidating when you first look at it.

What You Need to Know Before You Go

Visit in the Early-Mid Spring and Fall Unless…

St. Augustine’s Nights of Lights has become a famous event that takes place between mid-November and the end of January. People come from around the world to see the city all lit up during those 2 1/2 months. If you’re interested in seeing the Nights of Lights, I highly encourage you to go. However, you should know that it’s incredibly busy!

I recommend visiting in January because it’s less busy. It’s still busy, just less busy. Otherwise, in order to avoid the crowds (and the heat), I would recommend visiting in the early to mid spring and fall.

Consider Taking an Old Town Trolley Tour

Here’s the deal: Typically, I wouldn’t recommend taking a trolley around a destination because I believe that you get a more authentic and exciting experience by wandering through a city.
However, since you’re only spending 3 days in St. Augustine, you don’t have much time to wander and still see all of the amazing attractions. The trolley tours in St. Augustine are great because you’ll learn the history behind just about every building in the city. While there are plenty of plaques with historical information sprinkled around St. Augustine, you will definitely learn more from the trolley tour. Plus, the trolley is flexible; you can get off at multiple destinations to explore the historical sites, and, once you’re done, you can board the next one that comes by. While you can walk to pretty much everything in St. Augustine, the trolley can be especially nice if you are traveling with children.


3 Days in St. Augustine Itinerary Recap

Just to make sure you don’t forget any of this awesome information, let’s quickly go over it again.

Day 1

  • Tour Flagler College
  • Explore the Castillo de San Marco
  • Walk Down St. George Street
  • Take You Photo by the Original City Gate
  • Take a Ghost Tour

Day 2

  • Go to the Beach
  • Climb the St. Augustine Lighthouse
  • Tour San Sebastian Winery and Taste the Wine (for FREE)
  • Enjoy the Nightlife

Day 3

  • Visit the Alligator Farm
  • Take a Sunset Cruise

Where to Stay

  • Casa Monica
  • Bed & Breakfast

Where to Eat

  • Burrito Works Taco Shop
  • Pizza Time
  • Prohibition Kitchen
  • The Columbia
  • The Floridian

Things You Need to Know

  • Visit in Early-Mid Spring and Fall or January
  • Consider Purchasing Green Trolley Tickets

So there you have it! That was your ideal 3 day St. Augustine itinerary! Aren’t you just totally excited to go now?! I sure hope so!

Author Bio: Jennifer Meyer is a travel blogger who shares her best budget travel tips and destination guides on her blog, Roads We Wander. She loves helping people explore the world on a tight budget. Follow her on Pinterest, Instagram, Facebook and Twitter.


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Weekend in St. Augustine, Florida 2 or 3 Day Itinerary Weekend in St. Augustine: The Best 2 or 3 Day Itinerary



  1. We’ve been several times and have never done a Flager Tour or the lighthouse. Definitely on the list for the next time driving out of FL!

  2. How cool! I never really thought of visiting here but it sounds and looks wonderful

  3. We LOVE St. Augustine! The winery is great! Just down the street is the distillery, which offers a really fun, free tour if you make it back! The Ice Plant restaurant attached to it is also really good (pricey, but amazing). Would love to try the Prohibition Kitchen! That sounds like my kind of place 🙂

  4. Thank you! We’re making a list of things to do and wanted just a few days plan and have two kiddos. This is perfect

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