3-Day Orlando to St. Augustine Itinerary from Someone Who’s Visited

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One of the most relaxing road trips you can take in Florida is going from Orlando to St. Augustine. Why?

Well, for one leaving the crowded roads of touristy Orlando behind feels so liberating, and second, it’s a road trip you need to take if you’re visiting Florida.

Not only will you get to enjoy the wonderful scenery, but you will get a chance to escape into a blissful beach vacation. Sure, there are a lot of different beaches in Florida, and not all are alike.

St. Augustine for one is known as the oldest city in Florida and there is so much history you can learn. Hopefully, the St. Augustine itinerary will not only guide you but inspire you to take that trip soon!

How to take the road trip from Orlando to St. Augustine

Taking the road trip from Orlando to St. Augustine is probably one of the easiest most direct to get on the road trip. Use your Maps, Google Maps, or any GPS to find the quickest route up to St. Augustine. If you don’t have one then use these simple directions to get there. Here’s what you’re looking at.

Approximate Distance: 107.3 miles

Approximate Time: 1 hr 49 min


From Orlando

Take the 1-4 East

Take the I-95 North toward Jacksonville

I-95 East

Exit 298 onto the US-1 for St. Augustine

How to get from Orlando to St Augustine

Rent a car

Renting a car at the Orlando International Airport is probably one of the best ways to get to St. Augustine. The convenience of being able to drive from Orlando to St. Augustine makes up for any other option.

If possible rent a car. However, don’t worry if you can’t rent a vehicle, since there are plenty of other options available. 


Second, if you want to do rideshare or try Uber or Lyft, then these are viable options. Don’t forget that these may be more expensive depending on the distance to get to Saint Augustine. 

Furthermore, when you make it into the city, you can Uber and Lyft your way around town but there are other options (more on that later).

Though you may enjoy it more if you walk or take the Old Trolley Tour. You’ll see much more and learn the history along the way.


Finally, another option is taking the Greyhound buses to St. Augustine. Although these may differ quite a bit depending on where you plan on getting it from. For example, a typical round trip from Orlando to St. Augustine may cost anywhere from $21-$30. Though rates may vary depending on the season! 

The 3-day Itinerary from Orlando to St. Augustine

Day 1 

Start by Exploring St. George Street. 

st augustine george street

Walk through the little shops of the downtown area. There is a lot to see. You can catch anything from cute little boutiques, eateries, and more.

When lunch rolls around then be sure to eat at one of the delicious restaurants here.  

In this area, you will be able to visit the colonial quarter and Plaza de Constitucion. They are within walking distance. In addition, visit the Church, it is probably one of the most unique attractions to see here. 

Day 2 

Spend your day at Saint Augustine Beach. You can rent an umbrella and beach chairs on the beach. If you have children, then you take your kiddos to the playground. It is the perfect place to keep your kiddos entertained for hours. 

Walk the Pier St. John since it is one of the best views to catch! It’s the perfect place to walk and catch some spectacular photography.

Day 3 

Explore the popular Attractions with the Old Trolley Tour. Make sure you go early to take advantage before they close the last train.

One time I missed the last train stop at 3 pm. Bummer, I did not catch the tour that time. So be sure you arrive early. Not only will you see a lot more but you’ll have time to hop on and off the train as many times as you want!

What I love about this trolley tour is that you hop on and off an unlimited number of times. There are a number of popular locations.

You can either pay for a one-day pass that costs approximately $27 or pay for a two-day pass which will cost you $37.

Double-check with them to find the correct schedule and cost. It really is the best way to get to know the city and the history behind it!

Things to do in St. Augustine

st augustine flagler college
  • Take the Old Trolley Tour
  • Visit the Fountain of Youth
  • The Old Jail House
  • The downtown of St. Augustine
  • Visit Castillo de San Marcos
  • Visit the Old House Museum
  • Colonial Quarter
  • Bay Views
st augustine bay views
  • Villa Zorayda Museum
  • Lightner Museum
  • St. Augustine Distillery
  • San Sebastian Winery
  • Whetstones Chocolate Factory
  • Old Senator Tree
  • Spanish Military Hospital Museum
  • Plaza de Constitución

Places to Stay in Saint Augustine Florida

Top 3 Hotels

Casa Monica Resort and Spa, Autograph Collection

Hilton St. Augustine Historic Bayfront

The Courtyard by Marriott St Augustine

Top 3 Budget-Friendly Hotels

Castillo Real, Ascend Hotel Collection

Guy Harvey Resort on Saint Augustine Beach

La Fiesta Ocean Inn & Suites

Tips to Remember

Though St. Augustine is a smaller city and you can easily check it out in a day or two, don’t forget that there are some things you should remember

orlando to st augustine itinerary
  • Find an all-day parking lot so you can leave your car (some parking areas don’t let you leave and come back so make sure before you are about to park your car for the day) There are different rates in different places. These can range anywhere from $23- $50+ depending on where you go. 
  • Bring comfortable walking shoes for all-day walking. FYI there is a lot of walking in the downtown area and you will definitely count on your legs for that;
  • Also, bring an extra pair of shoes in case of rainy weather, I have found that flip-flops work really well in the rain. Trust me, the water is warm on a rainy day. 
  • Bring a poncho/ umbrella – With Florida’s unpredictable weather, I have been both in rain and sun in St. Augustine and it’s always better to expect both since they can be very unpredictable. 
  • Bring Bug Spray. I don’t know why, but the mosquitos are probably one of the most vicious in Florida. I know they love me because I had quite a few just from wearing shorts. The weather is warm so you must own shorts or light fitting clothing. Definitely, bug spray is a must!


St. Augustine is known as the oldest city in Florida. With so much history surrounding, there is no reason why St. Augustine should not be in your top choices to visit and travel.

st augustine itinerary

Using the Orlando to St. Augustine itinerary should give you an idea of what to expect when you do visit. Sure if you are reading this during the most vicious worldwide pandemics, then traveling may not seem all that possible.

However, no excuse as to what to plan for when you visit this historic city.

St. Augustine is one of my favorite cities to visit in all of Florida. There is so much history and you learn so much from a simple visit.

st augustine church

I find that anywhere from 2-3 days is best to take in the whole experience. I find that one day is too rushed and three days is just perfect. It gives you the right amount of time you need to plan, visit, and explore this historical city! Of course, you can always stay longer, since this city has so much to offer.

Let me know what you enjoyed most about this city!


Jess & Jeanette

Jess and Jeanette, two sisters who founded Unseen Beaches, were inspired by their family’s beach vacations while growing up.

Their passion lies in guiding you toward the most remarkable beach destinations across the U.S., while also protecting and preserving these beautiful coastal treasures! 🌊❤️

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