Explore Florida’s historic coast with this two day St. Augustine itinerary. This guide will help you plan things to do, what to eat, and where to stay. If you have more time, check out the amazing day trips from St. Augustine.
As a beautiful historic city set right along Florida’s northeast coast, St. Augustine has a little something for everyone. Downtown St. Augustine showcases Spanish Revival architecture with its ornate historic buildings and charming cobblestone streets, while the bay and white sandy beaches offer a gorgeous backdrop for a relaxing holiday.
St. Augustine’s main claim to fame is as America’s oldest city. The area was named by the Spanish soldier and explorer Pedro Menéndez de Avilé, who came across the area on August 28, 1565, the feast day of St. Augustine. While the area has traded ownership over the years, it’s been continuously occupied since the sixteenth century.
On our road trip through northern Florida, we spent several days in St. Augustine at the start, and then a few more at the end. I’ve condensed our trip down to a two-day itinerary in St. Augustine. In just a weekend in St. Augustine, you can cover most of the historic downtown and spend some time relaxing at the beach.
If you have more time in the area, I’ve also included the best day trips from St. Augustine.
How to get to St. Augustine, Florida
St. Augustine is located on the northeast coast of Florida, bordering the Atlantic Ocean. It’s located about 45 minutes south of Jacksonville, which is also the closest airport (JAX). Most major airlines fly into JAX.
The city of Orlando is about a 1 hour 40 minute drive away, while Orlando’s MCO airport is almost a 2 hour drive.
How to get around St. Augustine
The historic downtown area of St. Augustine is compact and pedestrian-friendly, so you can spend most of your time on foot while you’re in the city. A trolley tour is also a great way to get around St. Augustine as your pass is valid for the whole day, and you can hop on and off at the different stops.
If you’re planning on going to the beach or taking any day trips, I’d recommend renting a car.
Where to Stay in St. Augustine
There are two main hotel areas in St. Augustine – the historic district and St. Augustine Beach. If you’re planning more activities in downtown, then check out these convenient options below.
St. Augustine Historic District Hotels
Double Tree Hotel St Augustine Historic District – I’m a sucker for the DoubleTree cookies, but the super convenient location and comfortable, updated rooms make this an easy option.
Hilton St Augustine Historic Bayfront – This hotel is located right across the street from the Matanzas River. While the building is historic, the rooms are recently updated.
Casa Monica Resort & Spa, Autograph Collection – This is a unique luxury hotel that was originally built in 1888 central to historic downtown St. Augustine. The building features stunning Moorish architecture and decadent interiors.
St. Augustine also has a lot of cute bed & breakfasts in town that have a lot of charm. Most of these are listed on booking.com. We typically use booking.com when possible because of the flexible cancellation policy and the discounts and rewards that come with its Genius program.
St. Augustine Beach Hotels
If beach time is your priority, then check out the Embassy Suites St. Augustine Beach. It’s right next to the pier on the beach, so you can walk outside your hotel to catch sunset or sunrise.
Where to eat in St. Augustine
Breakfast: Don’t miss Island Donuts. We make at least one stop for donuts wherever we go (I think we got up to three on this road trip), and Island Donuts was the clear favorite.
Lunch: If you’re after burritos or tacos, we liked Mojo’s Tacos. Crave was a great healthy lunch option.
Dinner: If you’re after a more formal dining spot, Aaron came here for work over 5 years ago, and still remembers his meal from the Floridian.
Treats: The Hyppo is a local favorite for unique flavored popsicles.
St. Augustine Itinerary
Day 1: Downtown St. Augustine
This first day is all about exploring downtown St. Augustine, and seeing what makes this historic city so unique.
1 Take a Trolley Tour or Walking Tour
In a small, historical city like St. Augustine, a trolley tour is an easy way to get a lay of the land and learn more about the city’s past.
The St. Augustine Hop-On Hop-Off Trolley Tour lasts about 1.5 hours from beginning to end, but you can hop off at any one of the 22 stops around the city to explore more. The trolley runs about every 15 minutes, so you usually don’t have to wait long for the next trolley when you’re done with a stop and ready to hop back on.
These trolley tours are guided by the driver, so each one is a little bit different. But, the reviews are overwhelmingly positive, so you’ll be sure to have some fun and learn a lot no matter who’s leading your tour!
- Adults $34
- Children (ages 4-12) $18
- Free parking available at the Old Jail Complex
To explore a little deeper, take a walking tour. There are several themed options, including a ghost walking tour and a craft beer walking tour. If you just want straight history, the St. Augustine historic walking tour starts with the first recorded Thanksgiving in 1565. It covers the city under both Spanish and British rule, and gives the background on most of the buildlings and attractions around town.
2 Stroll down St. George Street
St George street is the main pedestrian-only thoroughfare in St. Augustine. This fun, busy street is lined with shops, restaurants, and ice cream parlors.
If you start on the north end, you’ll walk through the old city gate, built in 1808.
A few things to keep an eye out for (these run from north to south):
- Oldest wooden school house
- The Spanish Bakery – pick up some empanadas or traditional cinnamon cookies
- Whetstone Chocolates – local chocolatier known for fudge and artisan chocolates
- The Hyppo Popsicles – there are a lot of ice cream shops on St. George Street, but The Hyppo is a homegrown favorite that creates unique flavors
- Pena-Peck house: Built in 1750, originally the home of the Spanish King’s royal treasurer Juan Esteban de Pena.
3 Pop onto Aviles Street
Aviles Street runs parallel to St. George Street, so after you’ve made your way down, pop one street over. Aviles is a cute cobblestone street that dates back to the 1570s.
4 Tour one of St. Augustine’s historic buildings
As you would expect in a city with this much history, there are some buildings with gorgeous architecture and an interesting past. These are a few buildings you can tour in St. Augustine.
Flagler College Historic Tours – Tours run two to three times a day and cost $16 per person. Flagler College was built by railroad magnate Henry M. Flagler in 1888. It was originally the Hotel Ponce de Leon, a luxury hotel popular with wealthy northerners as a winter getaway. It is considered one of the finest examples of Spanish Renaissance architecture.
Lightner Museum – The Lightner Museum is worth a visit both for its collection as an art museum and for its architecture. The collection is mostly American Gilded Age pieces. Similar to Flagler college, this structure was built in the Spanish Renaissance Revival style originally as the Hotel Alcazar.
Old Jail Museum – This building isn’t in the same league for beauty and decadence as the first two, but the Old Jail still offers some interesting history about St. Augustine’s most notorious criminals.
5 Explore the Castillo de San Marcos
The Castillo de San Marcos was originally built by the Spanish between 1672 and 1695 to defend their Florida territory. The fort was built with coquina, which is soft limestone of broken shells. As you get up close, you can actually see all of the tiny shells crushed together in the stone. The fortress was designed to withstand the impact of cannons and is the oldest surviving masonry fortress of its kind.
The Castillo has traded ownership over the centuries through diplomatic means, but impressively, it was never captured in battle.
- Free for up to four people with National Park Pass as it’s a National Park site.
- $15 for ages 16 and up
This fort sits right along the bay. It’s an amazing spot for both sunrise and sunset. There’s also a junior ranger program for kids (and the adults with them) to learn more about the history of the fort.
6 Take a Scenic Cruise
While it’s beautiful to look out over the water from the Castillo, it’s fun to get a look back at the city on the bay. Hop on a boat with Scenic Cruise of St. Augustine.
- Adults $20.75
- Children (ages 4-12) $9.75
This scenic cruise goes in a big loop around the bay and under the Bridge of Lions, so you get a view back at St Augustine, and reach the lighthouse before turning around. This ride is pretty light on commentary, so go for the views. We went a bit before sunset to catch the city drenched in that soft, golden light. It can also be pretty breezy, so many sure to bring a jacket.
Day 2: St Augustine Beach, Alligator Farm, Lighthouse
Now that you’ve explore the heart of St. Augustine, it’s time to venture a bit for day two on this St. Augustine Itinerary.
1 Hang out at St Augustine Beach
First up, we headed to the beach. I’ve learned that many east coast beaches tend to get windier as the afternoon goes on. Morning is a good time to enjoy the beach before it gets super busy and usually with better weather.
St Augustine Beach Pier – There is a large parking lot in front of the pier (with free parking!)
Anastasia State Park Beach – This beach is just north of the Pier. You can either walk north of the pier, or park in the state park parking lot (which costs $8). The parking lot is at the very south part of the park, so getting to the north part of the park (and Anastasia Islands) either means a lot of walking or bring a bike/ebike. Or just hang out at the southern part near the pier.
Surfing in St Augustine
Some of the more popular St. Augustine surfing spots are in this north part of Anastasia State Park Beach. There are technically three surf spots in Anastasia State Park: The Entrance, Middles, and Blowhole. While we were there, we saw a lot of locals heading up north on the bike with the boards and ebikes. But if you’re visiting and hoping to surf, Aaron still found some decent waves not too far north of the pier. Check the St. Augustine surf forecast on Surfline.
And if you’re in the market for some new surf gear, check out our budget-friendly favorites here.
2 Visit the Alligator Farm
We don’t typically seek out zoos when we travel, but the Alligator Farm seemed like a good chance to learn more about one of Florida’s most notorious native species, the alligator. This is a great stop to include on your St. Augustine itinerary if you’re traveling with kids.
- Adults $28.99
- Children (ages 3-11) $17.99
Our favorite part was the main alligator swamp which had several dozen alligators swimming around or sunning themselves on the sand. We were able to catch two different zoo keeper talks at the swamp. The keeper shared a lot of interesting facts about alligators (they have 24 different species at the zoo). She also showed off some of the training they do with the alligators, like opening wide to check on all of those pointy teeth!
The Alligator Farm has a lot more than just alligators. We really loved the macaws, the sloth, and the Komodo dragon. There is even a large natural aviary where you can see local birds roosting or passing through.
3 Climb to the top of the St. Augustine Lighthouse
The St. Augustine Lighthouse is located on the north end of Anastasia Island, so it’s a stunning spot to enjoy 360-degree views of St. Augustine, the bay, and the beach. We climbed up all 219 steps just in time to catch sunset.
- Adults $14.95
- Children (ages 12 and under and 44″ or taller) $12.95
Kids under 44” are free, but they also can’t climb to the top of the lighthouse. We had to switch off since we now have a baby in tow. A few unique tours are offered at the Lighthouse, including a ghost tour and a moonrise tour with champagne and hors d’oeuvres.
4 Head back to the pier for sunset
If the sun isn’t completely set by now, I recommend making your way back to the pier or the beach for sunset.
Day 3: Day Trips from St. Augustine
If you’re looking for more beyond a two day itinerary for St. Augustine, then there is so much more to explore in the area. We had a few extra days, so we made our way up and down the coast, and even went inland. Here are some of the best day trips from St. Augustine.
Hunt for shark teeth at Mickler’s Landing, Ponte Vedra Landing
The beaches north of St. Augustine are known for large shell deposits, and sometimes even shark teeth! We spent the morning walking along the sand and keeping an eye out for anything small, black and shiny. We lucked out and ended up finding a few shark teeth!
Walk the beautiful gardens at Washington Oaks Gardens State Park
These formal gardens are bursting with color from azaleas and camellias, and shaded by ancient majestic oak trees. The gardens were originally created by a wealthy couple in the 1930s that used the area as a winter retirement home. The gardens were gifted to the state in the 1960s so they could continue to be enjoyed by visitors. This is a popular spot for wedding and engagement photography.
Entance is $5 per vehicle, and also includes parking at the beach across the street. This beach has some of the only rocky shoreline in Florida.
Visit crystal blue natural springs in Ocala National Forest
Ocala National Forest is dotted with blazing blue natural fresh water springs that stay 72 degrees all year round. Most are located about 1.5 hours from St. Augustine.
Book a round of Golf at TPC Sawgrass
We stayed a night at the Sawgrass Marriott and saw the beautiful golf courses as they were prepping it for a tournament. TPC Sawgrass features two PGA tour championship courses.
Ready to explore St. Augustine?
Pin this itinerary to help you plan your trip!
How to Kayak and Swim with Manatees in Crystal River, Florida
Friday 27th of May 2022
[…] Planning a road trip around northern Florida? Don’t miss the history and beautiful beaches in St. Augustine! […]