Last updated on June 26th, 2023 at 06:51 pm

Do you know where is the oldest European settlement in mainland USA located? The answer is not Jamestown, Virginia which is where the British settlement started.

It was the Spanish who formed the first ever settlement in the USA in 1565 at this historic town in Florida called St. Augustine. Jamestown was formed in 1607, almost 40 years later! This quaint town is one for the romantics. While one would think of French quarters in New Orleans or Quebec City or Charleston when thinking about a touch of Europe in North America. We will take you through an off-the-beaten path in this 3-day itinerary of St. Augustine.

This trip was very special to us since we were celebrating our 5^th anniversary and babymoon last Jan. A short flight away from the east coast this is a not to miss destination in Florida.

In this blog post, we will take you from old forts to distilleries, from dining in 19th century homes to oak tree tunnels, from beaches to alligator farms thereby introducing you to the oldest city in the continental US.  Moreover, we’ll cover plenty of kid-friendly things to do in St. Augustine.

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Transportation & Stay

Flying into Jacksonville, the closest airport to St. Augustine is your best bet unless you are driving. We rented a car from Jacksonville airport and it took us only an hour to get to St. Augustine.

Parking: Street parking can be a pain within the historic quarters but the good news is that there is a paid parking facility which is conveniently located in the old town. If you get a hotel or one of the quaint BnB’s in the historic quarter then everything will be within walking distance for you.

We stayed in St. Augustine Holiday Inn which was 5 minutes drive from the old town. We ended up taking the old trolley tour to explore the historic quarter and drove to other attractions outside the old town.

Best time to go

I’d say go during the holiday season when the nights of lights are up. What’s that? If you ever wanted to be in a movie set that is lit up like a fairytale town then look no further unless you are going to Disney World. Luckily for us, the nights of lights are on until the end of Jan so we got to experience it in all its glory.

Having said that, I don’t think there is any bad time to visit St. Augustine except if you want to avoid extreme heat then don’t go in the summer months.

3 day itinerary for St. Augustine

Pretty much everything in this town claims to be the first in the country, from the wax museum to the drug store. Even the first Ripley’s Believe It or Not was opened in St. Augustine.

So let’s dive in –

Day 1 – Explore the Old Town

Hop-on-hop-off Trolley Tour

I am normally not someone who takes these tours unless I really think I need to know the history of a place. And trust me you want to know the history of St. Augustine to fully appreciate this town.

There are two Hop-on-Hop-off trolley companies, Red Train Tours and Old Town Trolley Tours. We rode with both of them and honestly, I’d recommend them both. In our experience, they both had excellent tour guides who narrated the history of the town and fun anecdotes along the way.

The first stops of the Old Town Trolley Tour are The Old Jail, Oldest Store Museum, a few things that I’m the kids will enjoy the most. TIP: This would also be a great place to park your vehicle as they have a big parking lot in the back.

Colonial Quarter 

The best way to explore is to walk around the historic colonial quarter and explore the old houses turned into restaurants and shops. TIP: Check out Hypolita St. & St. George Street (pedestrian mall), and the main City gates. If you are taking the hop-on-hop-off train, it’s effortless to make a stop at the historic town.  

Castillos de San Marcos

After exploring the historic quarters head to the fort which is a walking distance away. The story goes that given the location of this city, it would usually get attacked by pirates. Hence at the behest of the local people the Spanish King fortified the city and Castillo de San Marcos was build.

Today it is one of the National Parks Site, which means if you have your NPS pass bring it along otherwise there is a small fee to go inside the fort. The Castillo reminded us of the forts in Puerto Rico but only this was way smaller. TIP: If you don’t have the NP parks pass then I’d recommend skipping going inside since there isn’t much to do within the fortification.

You can, however, walk the perimeter of the outer fort walls FREE of COST. FUN FACT: Give a closer look and you’ll find that the walls and floors of the fort are made up of seashells.

DAY 2 – Beyond Old Town

Now that you have explored the main parts of the town let’s visit some iconic places around the old town.

Flagler College

Here’s one of the most iconic architectures in St. Augustine. Flagler College was originally built by Mr. Flagler as a seasonal resort called Hotel Ponce de Leon in 1888 for the rich and mighty of the North East to escape their brutal winters in the south. Today, it’s a private college and if you decide to take a tour, your tour guides will be one of the students.

We signed up for a guided tour of Flagler College and if you do not want to go on a guided tour I highly recommend that you walk through the beautiful courtyard gardens of this college which is FREE of COST.

FUN FACT: The artist who worked on creating magic on the dome of this hotel/college was later commissioned to work on the Library of Congress in Washington DC.

Lightner Museum

Opposite the Flagler College is the Lightner Museum which is another stunner when it is all lit up. If you really like museums then you must visit, in all honesty, we skipped this one.

Villa Zorayda Museum

Villa Zorayda was built by another Bostonian who themed his house after the Alhambra Palace in Spain. There is an entrance fee to tour the house and photography is not permitted inside. If you are really interested in antics and architecture then it’s worth the tour otherwise just enjoy the quirky building from outside.

Whiskey, Wine, and Chocolate Tasting  

After all those architecture tours, we were ready for some fun stuff. By that, I mean touring and/or tasting Liquor and chocolate.

• St. Augustine Distillery – We took a tour of the distillery and returned home with a fine bottle as our souvenir.
• San Sebastian Winery – Located very close to the distillery is the local winery. If you are not the one driving then go for tasting right after or before the distillery.
• Whetstone Chocolate Factory –Since I wasn’t consuming alcohol for a very good reason on this trip a tasting of chocolate was on the cards for me. What started off as a small family run business now has multiple locations all around the city.

Stroll the Historic District at Night

Come back to the historic district after your tasting shenanigans and experience the beauty during the evening and night. Or perhaps take a romantic ride in one of the horse carriages. TIP: We’d highly recommend dining in one of the centuries-old buildings turned into restaurants here. We have given some of our dining recommendations at the end of this post.

DAY 3

If you think you’ve had enough of the city then take this day to hit the beach or go swimming with dolphins at Marineland Dolphin Adventures. Otherwise here are some other things to do in St. Augustine on your last day –

Fountain of Youth

Don’t expect to return 10 years younger after your visit. This is in fact the site, which once was a Native American village, where the Spanish sailors landed in mainland USA. It’s a huge expanse of an Archeological site where you can expect to find dancing peacocks to flaring gunshot enactment from the colonial time. If you are traveling with family, kids will love it here. There is an entrance fee to visit.

Magnolia Avenue

Rated as one of America’s most beautiful streets by National Geographic, we couldn’t agree more. You will pass this street lined with aged oak trees as you drive to the entrance of Fountain of Youth but what’s more important is you don’t miss the tree tunnel photo op here.

Ripley’s Believe It or Not!

This is where it was all started by Mr. Ripley, which makes for another fun family-friendly activity in St. Augustine. FUN FACT: This is the first Ripley’s Believe It or Not in the world.

St. Augustine Light House & Museum

Tussled behind another array of aged Oak trees is the historic lighthouse. The lighthouse was closed when we got there but I bet the views from the top would be worth the money. Next to the lighthouse is a beach in case you want to get sun-kissed.

St. Augustine Alligator Farm

Very close to the lighthouse is an Alligator farm which I bet kids and adults alike would enjoy.

Find fun things to do in St Augustine, Florida!

Where to Eat and Drink

Below are some of the restaurants and bars in St. Augustine that we tried and would definitely recommend them to you all –

• Preserved (1860’s historic house turned into a restaurant)
• Raintree
• The Floridian
• Tini Martini Bar
• Odd Birds
• Spanish Bakery
• Maple Street
• Blue Hen Cafe
• The Kookaburra Cafe

Where to Stay

We stayed at Hampton Inn just a mile away from the historic quarters but for a unique stay in St. Augustine consider staying in one of the boutique BnB’s in the historic old town.

I hope you all enjoyed this guide and will have a fabulous time in St. Augustine. Don’t forget to pin this post for later and share it with friends and family.

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Happy & Safe Traveling!