Are you planning 3 days in St. Augustine and feeling overwhelmed by all the options of things to do and see? I know I was! There are so many things to experience in this Old City; whether you like history, food, adventure, nature, art, music, or photography, there is something for everyone to enjoy.
Contrary to being the oldest continuously occupied European-founded city in America, I think of youthfulness when I hear St. Augustine. Not only because it is a dynamic city but because it’s also the first location in the United States that my husband and I traveled to not long after our wedding.
At 23, I was fresh out of college with big dreams, and exploring as many places as possible was one of those. I like to say St. Augustine contributed to my desire and love for travel since I haven’t stopped since our first long-ago visit. Now, 12 years later, we found ourselves back in St. Augustine, seeing familiar places while seeking new adventures.
This time, it took me a little while to figure out what we wanted to do to make the most of our 3 days in St. Augustine. This city has many possibilities, and even though you’ll want to do them all, it’s impossible to squeeze everything in 3 days.
To help you decide what to see or do, I’ve created this itinerary on how to spend 3 days in St. Augustine. Plus, I’ve included a few visiting tips to help you navigate this fun-loving city!
Who Should Use Itinerary for 3 Days in St. Augustine?
We’ve all been there before. Sometimes the best vacations are the most spontaneous with on-a-whim decisions. And while I love to plan, I am hesitant to write itineraries because sometimes life happens and things change. For example, unexpected travel delays, closures, and long wait times can cause havoc in a well-thought-out travel plan.
Regardless, this 3 days in St. Augustine guide will give you great suggestions and options on what to do in St. Augustine, even if you don’t have enough time to see everything or simply don’t want to do it all. If you have young children, you may also need to cut or change some of these places in the schedule depending on their needs.
Some people, including my husband, might even think this itinerary is too ambitious, but I love to make the most of my vacations by seeing as much as possible!
The good news is that St. Augustine is a very walkable city, making it easy to get to many destinations. It’s possible to walk or bike to many of these places on this itinerary, but you can also call an Uber or rent a car for locations a little further from the heart of downtown.
This 3 days in St. Augustine itinerary is also great if you love:
- History
- Nature
- Travel photography
- Looking for ideas for a long weekend getaway
- Seeing the most you can in a short amount of time
Is 3 Days in St. Augustine Enough?
Yes and no. Honestly, I find it challenging to see St. Augustine in three days. There are many things to do and see, but if you only have three days, it’s possible to see the main points of interest. Just prepare that you may have little downtime if you plan to see all the highlights.
What is the ideal amount of time to visit St. Augustine? That’s hard to say, depending on what you want to do, but five days at least will give you an excellent taste of the city with a less jammed-packed schedule.
St. Augustine’s Rich Historical Past
You’ll hear many tour guides say this: St. Augustine is the oldest continuously occupied European-founded city in the United States. It dates back to the 16th century and is steeped in history, with several cultures shaping what St. Augustine is today.
If you sat in an American high school history class, you already know all about European colonization in North America and the power struggles for the new territories between the major European powers: French, Dutch, Portuguese, British, and Spanish. The founding of St. Augustine is one of many examples of these territorial conflicts, as the Spanish weren’t happy, to say the least, when the French Huguenots moved into Northern Florida.
To resolve this conflict, Spain commissioned conquistador and officer Pedro Menéndez de Avilés to maintain control and drive out the French, which he successfully did so. Pedro Menéndez de Avilés founded St. Augustine in 1865 in response to the growing French threat.
You can still see the Spanish influence in St. Augustine’s culture, architecture, and cuisine present-day. But it wasn’t just the Spanish who influenced the “Nation’s Oldest City.” The Native Americans, Irish, Africans, Minorcans, British, Greeks, and others have all had their hands in shaping the city we love today.
The Spanish, Native Americans, Irish, Minorcans, Africans, British, Greeks, and others have shaped and influenced the city we see and love today.
When is the Best Time to Visit?
We’ve been to St. Augustine in mid-April and early September; both times were pretty toasty, although April is usually milder than September. Plus, there is less risk of a hurricane in spring than in summer and fall. Hurricane season runs from June 1 to November 30.
Usually, you’ll have cooler temperatures, less rain, and fewer crowds if you go during March through May. Hotels are typically cheaper during this time, too. School is only out of session if you visit St. Augustine during spring break (usually around late March and early April). We’ve been towards the end of spring break, but it was relatively quiet in the city compared to Florida’s beaches.
Some might disagree with me, but summer in Florida is miserable unless you are at the beach or near a pool. Anything from late May to early October is too humid. Average summer temperatures can range from the 80s to upper 90 degrees Fahrenheit. But the humidity makes it feel like it is 1000 degrees outside.
If you go during the warmer months, bring tons of water, sunscreen with a high SPF, a hat, and an umbrella for pop-up showers. The sea breeze near the water may be pleasant, but it can get hot quickly in downtown St. Augustine.
I’ve yet to make it to St. Augustine from November through March, but there is less precipitation and cooler temperatures during this timeframe. Unless you visit during the major holidays such as Christmas, hotels might be cheaper in winter than in summer. Plus, I’ve heard that Christmastime in St. Augustine is dazzling and magical with all the lights around the city!
Typically, March through May is the best time to visit St. Augustine for cooler temperatures, less rain, and fewer crowds.
Getting Around St. Augustine
As mentioned earlier, it’s easy to visit many places of interest in St. Augustine by walking or biking. However, you’ll probably want a vehicle to see beyond the historic downtown.
Parking can be a nightmare depending on when you go, but luckily, I’ve had no issues (yet) finding a spot. Many public metered lots have free parking after 5pm and on Sundays, but if you arrive between 8am and 5pm on all other days, expect to pay around $10-$18 a day. Some lots are $15 for just three hours!
We parked a few times at Trinity Parish near Plaza de la Constitución. It’s $15 for a day with in-and-out privileges. But if you park there, you may have to leave early or return at a specific time if they have a special event, such as a wedding. Also, the Historic Downtown Parking Facility is near St. George Street, which costs $15 per vehicle per entry.
Many first-timers to St. Augustine will take the trolley. The Old Town Trolley tour gives an excellent overview of St. Augustine, with 22 hop on and off stops. Tickets are pricey, but you can see many St. Augustine highlights if you plan your day in advance. They also have a 2-day trolley ticket for a discounted price.
You can utilize and rearrange this 3 days in St. Augustine itinerary based on the trolley schedule if you aren’t driving. For more information and ticket prices regarding the Old Town Trolley tours, visit their website here.
Address for the Old Town Trolley (where it starts): 167 San Marco Avenue at the Old Jail Museum
Main Highlights of this 3 Days in St. Augustine Itinerary (Excluding Restaurants)
- Day 1: Flagler College, History Walk or Trolley Loop, St. Augustine Pirate Treasure & Museum, St. George Street, Optional Ghost Walk Tour
- Day 2: Old Jail Museum, Castillo de San Marcos, Lightner Museum, Aviles Street, Sunset Sail
- Day 3: Sunrise at St. Johns County Ocean & Fishing Pier, St. Augustine Lighthouse, Choose Your Afternoon Adventure (see St. Augustine Churches & Cemeteries, relax on St. Augustine Beach, explore Ponce de Leon’s Fountain of Youth Archaeological Park, have fun at St. Augustine Alligator Farm Zoological Park, or visit Anastasia State Park)
Day One:
Have a Bruncharcuterie at Ancient City Brunch
Address: 210 St. George Street C3, St. Augustine, FL 32084
For day one of your 3 days in St. Augustine, start with a hearty brunch at Ancient City Brunch. You’ll probably want to wake up early to grab a seat at this well-liked St. Augustine restaurant.
Ancient City Brunch Bar can be expensive, depending on what you order, but it’s a fun place that many people rave about and is one of the best places to grab brunch in St. Augustine. They create a fun twist to the charcuterie board by creating a “bruncharcuterie.”
They have many choices to build your bruncharcuterie, including favorites such as Belgium waffles, bagels, bacon, fruit, gouda pimento cheese, veggies, and more.
At first glance, there are so many options that their menu can be slightly confusing. We had to ask for clarification and still managed to order the wrong thing, but it didn’t matter because the breakfast sandwich we received was tasty.
The restaurant is tiny, so you may have to wait to get a table or take your food to go. There are also tables you can share with people you don’t know, giving you an opportunity to talk with the locals!
Stand in Awe at Flagler College’s Spanish Renaissance Architecture
Address: 74 King Street, St. Augustine, FL 32084
Cost: $17 per person for the guided tour
I wish I had discovered Flagler College before making my college selection, as this campus would have been my number one pick. If you walk around Flagler College, you’ll understand why. The campus has beautiful Spanish Renaissance architecture, tall towers, an impressive Rotunda, and a stately courtyard.
Flagler College wasn’t always a college, however. It was once Hotel Ponce de Leon. Industrialist and business owner Henry Flagler came to St. Augustine due to his wife’s poor health and, in doing so, noticed St. Augustine’s growing potential. He started building luxury hotels, including Hotel Ponce de Leon, constructed in 1885 through 1886.
This expensive hotel was for the wealthy and famous, with notable guests, including President Teddy Roosevelt, Mark Twain, Andrew Carnegie, Joseph Pulitzer, and more. Throughout the campus are lavish furnishings, woodwork, and 40 stunning Louis Comfort Tiffany stained glass windows in the ornate dining room.
While touring Flagler College, you may also notice outside the tall smokestack used to generate electricity. With the Edison Electric Company, Hotel Ponce de Leon was one of the first buildings in America to have electricity. I can’t even imagine the news that must have made back then!
Today, you can walk around this decorous college on your own or take a guided tour. If you choose to see it on your own, just be aware that your tour will mostly be limited to outside because this is an active campus with limited access to many interior rooms.
Daily guided tours start in the Rotunda located at 74 King Street. This one-hour guided tour will allow you to go beyond the lobby and see the dining room and Flagler room. Find more information about Flagler’s Legacy Tours here.
Take a History Walk or Complete the Trolley Loop
If this is your first time going to St. Augustine, take a historic walking tour or the approximate 80-minute narrated Old Time Trolley tour that takes you around the main points of interest in St. Augustine.
Departing every 15 to 20 minutes at each stop, the trolley tour gives you an overview of St. Augustine with an option to hop off the trolley if a particular place piques your interest. Find more information about the trolley tours here.
We opted for a historical walking tour for our latest trip to St. Augustine. The tour was a bit more intimate than the trolley since they limited it to 10 people or fewer (we only had four people, including me and my husband, on the day we went).
There are several historical walking tours in St. Augustine, but we went with the tour given by St. Augustine Experiences. The hour-long tour covered over a mile of walking on flat terrain. While it is not a challenging walk, you’ll still want to bring comfortable walking shoes.
We learned about Aviles Street, the city’s grid system, Henry Flagler’s luxury hotels, Flagler College, Treasury Street, and the civil rights movement in St. Augustine while walking by some of the oldest homes in the city. Our tour guide also kindly recommended some of the best places to eat while staying in St. Augustine.
Tours are $25 per person. Find more information on tours with St. Augustine Experiences by clicking here.
Get Lunch and a Miami Vice at Boat Drinks
Address: 56 St. George Street, St. Augustine, FL 32084
This vibrant, colorful bar and restaurant was a suggestion from a friend that lives near St. Augustine. Boat Drinks is your place if you love a fun tropical atmosphere or rum. They have an excellent selection of rum and is considered one of the top cocktail bars in the United States.
Getting a drink at Boat Drinks is also refreshing after a morning full of walking. They don’t have an extensive food menu, especially if you don’t care for seafood like me. I ended up with a double cheeseburger and rasta pasta, which was delicious, paired with a Miami Vice.
The tavern is small, and on the busy St. George Street, so you may have to wait for a table. They do have an upstairs bar, but it’s not always open.
Oh! And if time permits, come back for happy hour to get discounted drinks. Happy hour is Monday all day and Thursday – Friday from 3pm to 6pm.
Find Buried Treasure at the St. Augustine Pirate Treasure & Museum
Address: 12 South Castillo Drive, St. Augustine, FL 32084
Cost: Regular admission is $18.99 for an adult, $15.99 for a senior (ages 60+), and $9.99 for a child (ages 5-12). They also have annual passes and discounted tickets for military and Florida residents. Prices are subject to change.
After you’ve had your share of rum at Boat Drinks, make your way to the St. Augustine Pirate Treasure & Museum for an adventure. This museum may not be your cup of tea (or rum?), but we’ve been twice and always have a good time.
You will learn all about legalized privateers, what we call today “pirates,” Discover the infamous lives of Sir Francis Drake, Robert Searles, William Kidd, Thomas Tew, and Edward Teach, who you may know as “Blackbeard.”
You’ll see a wooden remnant from Sir Francis Drake’s shipwreck, Captain Kidd’s chest, one of two Jolly Roger flags that still exist, recovered treasure, and famous pirate movie memorabilia, including my favorite – Captain Hook.
The museum takes about 45 minutes to 1 hour to visit. Ticket prices are a little high, given it’s a smaller museum, but worth the visit if you enjoy pirate history and treasure.
Children will also have fun since there are interactive exhibits, including a “treasure hunt,” where they can receive a small prize if they find all the items. However, you may want to skip the exhibit on torture and punishment. It’s interesting, but maybe a bit too much for small children.
There is also an option to do a combo ticket that includes the St. Augustine Pirate Treasure & Museum and the Colonial Experience, giving you a chance to experience what life was like in the early days of St. Augustine. You’ll see a live musket demonstration, learn about blacksmithing, and climb a watchtower.
Find more information about the St. Augustine Pirate Treasure & Museum, including ticket prices and combo information here.
Explore the Famous and Lively St. George Street in the Historic District
You cannot miss this street during your 3 days in St. Augustine. It’s a bit touristy, but it’s worth the stop, especially if you are a first-time visitor to St. Augustine. Lined with boutique shops, older homes, restaurants, cafés, and more, St. George Street is the most visited street in downtown St. Augustine. It’s a pedestrian-only street, although cars can drive on the roads that intersect with St. George.
You can easily spend a whole afternoon exploring all the stores on the street. It’s also about a 1-2-minute walk to St. George if you are coming from the St. Augustine Pirate Treasure & Museum. Many people, however, will start at the Old City Gates at the northern end and make their way down the street.
Old City Gates
The Old City Gates was the entrance to St. Augustine during colonial America and provided a means of defense to protect the city. Built in 1808, the stone and coquina pillars still stand today and make an excellent spot for a photo opportunity as you begin your journey down St. George Street.
Oldest Wooden Schoolhouse in America and the Minorcans
Walking through the Old City Gates and continuing down St. George Street, you might notice a small wooden house on the right side of the road. This building is known as the Oldest Wooden Schoolhouse in America. Although the construction date is unknown, tax records show the house was there in the early 1700s. Today you can walk into this schoolhouse for a small fee.
During the early 1700s, the schoolhouse was located in the Minorcan Quarter of St. Augustine. Who were the Minorcans? They were people of Mediterranean origins who came to Florida as indentured servants to work on the New Smyrna plantation south of St. Augustine. After years of working on the plantation, the Minorcans moved northward to St. Augustine to establish a new life. Today, many people in St. Augustine are descendants of the Minorcans.
Read more about the Minorcans and early Greek settlers at the St. Photios Greek Orthodox National Shrine on St. George Street. It’s easy to miss, so you’ll probably want to pull it up on the map below or your GPS as you walk down the street.
Colonial Oak Music Park
Another popular place on St. George Street is the Colonial Oak Music Park. Sometimes, live performances occur here in the afternoon or evening under a massive 300-year-old oak tree. You can view the performance schedule on their website here.
Lined with boutique shops, older homes, restaurants, cafés, and more, St. George Street is the most visited street in downtown St. Augustine.
Grab Dinner at Casa Reina
Address: 1 Anderson Circle, St. Augustine, FL 32084
This may be unfair or not the best way to judge a taqueria, but I think if they have good salsa, then the rest of the food will probably be pretty darn good. I can easily devour a whole bowl of Casa Reina’s fresh medium-spicy salsa. With that said, Casa Reina has really good drinks and food, especially their tacos.
Casa Reina is just a short distance from St. George Street, about a two-minute walk if you head directly east from the Cathedral Basilica of St. Augustine. Indoor and outdoor seating provides a pleasant view of the marina and the famous Bridge of Lions. We were lucky to arrive after a brief rain shower with the sun finally peeking through, creating a beautiful rainbow over the blue Matanzas River. Unfortunately, I didn’t get a good photo of it!
“Wine” Down at Casa De Vino 57
Address: 57 Treasury Street, St. Augustine, FL 32084
Casa De Vino 57 is a cozy wine bar with outdoor seating in a covered courtyard. You can rest your feet here while sipping savory wine and listening to live music. And it’s only a few minutes’ walk from Casa Reina.
If you love red wine, try the Rawen Reserva Merlot from Chile. It’s delicious and bold. You can order by the glass or the bottle on select wines, but we decided to celebrate our first night in St. Augustine with a bottle. Cheers!
Optional: Delve Into the Spooky Side of St. Augustine with a Ghost Walk
Address: 76 Spanish Street, St. Augustine, FL 32084
Cost: $30 per person; the tour is only for ages 13 and up
After enjoying some wine, walk about thirty or so steps on Spanish Street to reach your next destination: The Odd Macabre. This quirky, small shop is in the cutest little building in St. Augustine, and inside, you’ll find many unique items. And as the name suggests, odd. You’ll also notice the wonderful fragrance when you walk through the door, as you can make candles here, too.
But we weren’t here for candle making. Instead, we booked the late-night Ghostorian’s Grimoire ghost walk (the North Route) for 9:30pm. I say “late” because anything past 9pm is usually bedtime for me.
Regardless of the time, I booked this guided tour because of three things: it has good reviews, they keep the group size small, and I didn’t want something theatrical or kitschy. And there are many, many ghost tour options in St. Augustine. I mean, it’s expected in the United States oldest continuously occupied European-founded city.
I’m happy with my well-researched decision because we had an outstanding tour with our guide, learning all about the creepy and mysterious things that went down in St. Augustine.
On the northern ghost tour route, you’ll most likely see the following:
- A bed & breakfast, formerly a funeral home
- The oldest cemeteries in the city
- Flagler College
- Plaza de la Constitución
- A love tree
You might ask: what the heck is a love tree? A love tree is where two different trees grow together. In this case, a palm tree and an oak. Legends vary, but it’s said that if two lovers kiss beneath the tree, their love will be eternal. However, if they separate for some reason, death awaits the doomed lovers—a sweet but possibly tragic tale.
You can also book a southern route tour for 8pm if you want to do something earlier. Both tours are $30 per person and only for those 13 and older. You’ll want to arrive at least 15 minutes before the start time. Please find more information on their website here.
Oh, you might ask…did I experience something spooky or paranormal? Yes, I did! We’ve done many ghost tours in various locations with no ghostly activity. So, I wasn’t expecting anything different for this tour, but I was dead wrong.
At the beginning of the walk, they’ll give you glow stick lanyards to wear around your neck. These glow sticks will relate to a story the guide shares at the first stop.
Now I tied my purple glowing lanyard in three tight knots. Part of me really wants to believe it wasn’t tied as tight as I thought, but I felt a little tug shortly after our guide concluded his story, almost as if the lanyard was pulled by someone or something…
Day Two:
Try an Aussie Pie and Kookaburra Coffee
Address: 24 Cathedral Place, St. Augustine, FL 32084
To start your second day in St. Augustine, snooze a bit and then grab an Aussie pie!
What is an Aussie pie? I had no idea until I stepped into Kookaburra Coffee, but it’s a pie no larger than your hand (think of a pot pie, but smaller). You can fill these baby pies with meat, veggies, gravy, cheese, and whatever your heart desires.
We ordered the coffee barista’s recommendation, “True Blue,” containing egg, cheese, and a sprinkle of rosemary. Pair it with one of their coffees, and it’s scrumptious!
There might be a line out the door for Kookaburra Coffee, but I promise it’s worth the wait!
Go Behind Bars at the Old Jail Museum
Address: 167 San Marco Avenue, St. Augustine, FL 32084
Cost: An adult ticket (ages 13+) can range from $16.99 to $18.99, depending on which day you go. A child’s ticket is $8.99 (under 4 is free). Prices are subject to change.
The Old Jail Museum is a short drive from Kookaburra Coffee; if you go there in the morning, there should be plenty of parking spaces. Or you can take an Uber or the trolley if you have tickets.
A very pink building will greet you once you enter the parking lot. You might even think you’re in the wrong spot, but you are not. That pink building is the Old City Jail, constructed by a company that later built the infamous Alcatraz prison.
Why does the Old Jail look this way? Well, Henry Flagler, you know, the same wealthy man who owned the hotel that later became Flagler College, knew that a jail was necessary for St. Augustine, but he didn’t want it to be downtown since it was not pleasing to the eyes. Plus, who would invest in a city with an ugly jail right in the heart of it?
His resolution to the eyesore issue: place the jail a little north of downtown St. Augustine on San Marco Avenue and make it look less like a jail and more like a hotel. In some ways, his plan was successful.
Today, 30-minute tours of the jail occur every 20 minutes starting at 9am on most days of the year. Guides dressed as inmates narrate the tour providing information about the jail’s history, including its notorious inmates. You’ll even get a chance to participate when they book you for jail!
While some topics covered may not be suitable for kids, they keep the tour entertaining and informative.
For information about the Old Jail and admission prices, visit their website here.
Take a Step Into the Past at Castillo de San Marcos: St. Augustine’s Early Defense
Address: 11 South Castillo Drive, St. Augustine, FL 32084
Cost: $15 per adult (ages 16 and up). Children 15 and under get in free. Only debit or credit cards are accepted. See their website for additional pass info. Prices are subject to change.
For your 3 days in St. Augustine vacation, you must visit the oldest masonry fort in the continental United States, the Castillo de San Marcos National Monument. The fort is just a short distance drive from the Old Jail Museum.
This fort helped protect St. Augustine in its early infancy. It is currently maintained by the National Park Services, with hundreds of thousands of visitors annually.
Dating back to 1672, the construction of the stone fort began due to the failures of wooden forts protecting the people of St. Augustine and Spain’s ships from enemy attacks.
The defense was a military base and was especially important in protecting Spain’s trade routes. It wasn’t until the late 1730s that plans were made to fortify the fort, including raising the walls to 35 feet.
Over the following decades, control and ownership of the fort passed from Spain to Great Britain, back to Spain, eventually landing in the hands of the United States. Castillo de San Marcos became “Fort Marion,” serving again as a military base and prison until the army left for the last time in 1900. After years of nonuse, the National Park Service took over the fort in 1933, and Congress restored its name to Castillo de San Marcos in 1942.
Today, you can walk around the fort’s walls and visit many interior rooms, including the old power magazine room, where you must crawl on your hands and feet (or squat really low) to reach. We call it the “creepy room” as it is dark, tiny, and feels slightly eerie as soon as you step inside.
Castillo de San Marcos is not free. Plan about 1 to 3 hours for your visit. You may want to visit early in the day as the fort is mostly outdoors without air conditioning.
Visitor Tip: There is a cannon demonstration, and many people will gather to watch it on the terreplein (the second floor of the fort). But along the outside of the East wall, you’ll get a better view of the demonstration with fewer people.
Devour Some BBQ for Lunch
Address: 5 Cordova Street, St. Augustine, FL 32084
Head on over to Mojo Old City BBQ for some southern cuisine, barbeque, and a chilled afternoon beer or cocktail. The restaurant is only a few steps away from Tolomato Cemetery and about a 5-minute walk from Castillo de San Marcos.
Their sauces are delicious on almost anything, especially the sweet and chipotle mixed on their beef brisket.
Immerse Yourself Into History at the Lightner Museum
Address: 75 King Street, Saint Augustine, FL
Cost: Adult tickets are $17. College students, military, and senior tickets (65+) are $14. Youth tickets are $10. Children 11 and under get in free. Prices are subject to change.
The next stop, the Lightner Museum, is a little further away – about an 8-minute walk straight down Cordova Street, or you can take a short drive there.
They have plenty of parking behind the museum in the public lot, but you must pay unless it’s after 5pm, a Sunday, or a holiday. Keep in mind that the museum is open from 9am to 5pm (the last admission is at 4pm), so it might be best to visit on a Sunday if you are driving and do not want to pay for parking.
We did not have time to see this historical gem on our last stop in St. Augustine. For this visit, I wanted to dedicate at least 2 to 3 hours to seeing the museum, which is probably the average time many people spend here.
This museum has temporary exhibits and permanent collections on multiple floors that include many beautiful works of art, Tiffany stained glass, an American Cut Glass Gallery, Gilded Age furniture and objects, and Otto Lightner’s (founder of the museum) collection of hobbies and curiosities.
The Lightner Museum was originally the Alcazar Hotel, and its large pool hosted many events. You can have lunch and step into what was formerly the biggest indoor swimming pool in the world in 1888. Traces of the former hotel can also be seen in the Russian and Turkish Baths on the second floor and the ballroom on the third floor.
Who commissioned this hotel’s construction? It’s none other than the same person who oversaw the construction of St. Augustine’s other opulent hotels during this time – Henry Flagler.
Find admission information and pricing for the Lightner Museum here.
Walk Down the Oldest Street in St. Augustine
Walking down St. George Street, you may think it’s the oldest street in St. Augustine because of its colonial architecture. That was my thought at first, but another road holds that title: Aviles Street. It’s a charming brick street with boutique shops, restaurants, and museums.
You’ll locate Aviles off the Plaza de la Constitución. Notice when you get to Aviles that it’s shorter and narrower than St. George and takes less time to explore.
If you don’t have time to explore these locations, at least walk down Aviles since it’s very picturesque with its colorful bricks and buildings.
The oldest street in St. Augustine is not St. George Street. It’s the charming and beautiful Aviles Street.
Have Dinner at Historical O.C. White’s
Address: 118 Avenida Menendez, St. Augustine, FL 32084
O.C. White’s dates back to the late 18th century and was one of St. Augustine’s first hotels. Today you can enjoy dinner inside or on their lovely, shaded patio near the marina. My husband enjoyed the shrimp, and I had a scrumptious southern-inspired meal: collard greens, brisket, and mac and cheese. You can’t go wrong at O.C. White’s!
Take a Sunset Sail on the Matanzas River
A sunset sail on a catamaran is the perfect way to end the second day of your 3 days in St. Augustine vacation. Cruise on the Matanzas River under the famous Bride of Lions, passing downtown St. Augustine and Castillo de San Marcos. If the waves aren’t too choppy, the catamaran might even take you close to Anastasia State Park and the St. Augustine Inlet that opens to the vast Atlantic Ocean.
You’ll see lots of wildlife, including dolphins and various species of birds. We were fortunate to see a dolphin pod up close; they were peeking their long snouts above the water, allowing me to capture a few shots with my film camera.
Multiple businesses offer these excursions, but we went with St. Augustine ECO Tours. We chose the catamaran for a more intimate setting, but they also provide boating expeditions if you are okay with being in a larger group setting.
The cost per person was $65 per adult, but well worth it to see St. Augustine from a different viewpoint.
Find more information about St. Augustine ECO tours here.
Pop In For a Quick Dessert at Le Macaron
Address: 8 Cathedral Place, St. Augustine, FL 32084
Oh, my goodness! I cannot say enough good things about Le Macaron French Pastries, which is a short walking distance from the marina. Their little macaroons are the perfect sweetness and not cloying.
But I really fell in love with their Nutella French beignets. Since we went to New Orleans, I’ve had a strong appetite for these delectable French pastries. Add Nutella to it, and I’m in Heaven. You have to stop and try one of these!
Plus, it’s fun to admire their hand-painted creations. They have desserts that resemble shoes, lipstick, bears, lips, hearts, and more!
Day Three:
Optional: Greet Dawn at St. Johns County Ocean & Fishing Pier
Address for the pier: 350 A1A Beach Blvd, St. Augustine Beach, FL 32080
If you are a morning person or don’t mind waking up a few hours earlier, visiting St. Johns Pier will reward you with a spectacular sunrise. Even if it is cloudy, the beach is still lovely for an early morning stroll. Plus, it’s a good way to start the last day of your 3 days in St. Augustine vacation.
The morning we went was magical and dynamic – storm clouds were in the far distance while the sun rose over the horizon, creating pink and golden hues. Many surfers were riding the glassy and dreamlike waves.
Given that it was around 6:45am, I was surprised by the number of people on the beach to see this incredible sight. We got some fantastic images with the pier in our frame.
It is possible to go on the pier, but they charge a $2 fee for sightseeing, so we opted to walk around instead. Also, parking is free and easy to find in the morning. You can park in the public lot next to the pier.
Visitor Tip: At the pier, the tide might be too high for you to walk down to the beach. If you want to sit on the beach to watch the sunrise, you may need to park further away from the pier. We parked on the side street near Island Donuts (16th Street). From there, it was a short walk down to the sand.
Grab Some Amazing Donuts and Coffee at Island Donuts
Address: 400 A1A Beach Blvd, St. Augustine, FL 32080
I didn’t think I would find a glazed donut as good as Krispy Kreme’s, but I was wrong! Island Donuts fresh donuts have the right softness, fluffiness, and sweetness. And they have many varieties too: glazed cinnamon roll, strawberry iced, Boston creme, orange creamsicle, s’mores, and old-fashioned, to name a few. They also have fritters, including a pineapple fritter, which many people rave about.
Grab a box of these fantastic donuts before heading to the lighthouse, or enjoy them in their small seating area. If you plan to watch the sunrise, you may be able to grab a box depending on when daybreak occurs.
They are open daily from 6am to 1pm.
Visitor Tip: The Bridge of Lions is a drawbridge. It opens to allow boat traffic, happening multiple times a day. You’ll want to factor this into your schedule when going to St. Augustine Beach (Anastasia Island). Traffic can sometimes back up.
Climb 219 Steps for a Panoramic View at the St. Augustine Lighthouse & Maritime Museum
Address: 100 Red Cox Road, St. Augustine, FL 32080
General Admission Cost: Adult tickets are $14.95. Senior tickets (60+) are $12.95. Tickets for children (age 12 and under) are $12.95. You must be at least 44 inches tall to climb the lighthouse. Check their website for promo codes for a discounted ticket (must be purchased online). Prices are subject to change.
A long time ago, a cat named Smokey parachuted off this lighthouse. Yes, you read that right. The lighthouse keeper’s son had this idea to see if cats could float. A terrible idea.
Thankfully, the kitty was okay but didn’t return for quite some time, and I don’t blame him. If I were the cat, I would never return!
And it’s a long, long way down. The St. Augustine Lighthouse is 165 feet high with 219 steps (14 stories!). It’s not a straight shot to the top, however. There are some landings where you can rest and catch your breath.
But when you make it up the 219 stairs, you’ll be rewarded with a pleasant view of St. Augustine. I’m afraid of heights, so I take my pictures quickly and go. Of course, coming back down is a lot easier than going back up.
What you see today is not the first St. Augustine Lighthouse. Its predecessor stood 350 closer to the Atlantic Ocean but tumbled into the sea because of shoreline erosion. The one you see standing was completed in 1874 and still shines today.
Also on the property are the keeper’s house, various exhibits, and nature trails. Parking is free, and there is an excellent gift shop to buy souvenirs. They even have plush stuffed animals named Smokey the Cat. Poor Smokey.
Visitor Tip: You must be at least 44″ or taller to climb the lighthouse. Also, if you are allergic to wasps, you’ll want to be careful since paper wasps are sometimes at the top. You’ll want to read the safety pamphlet they give you before starting your ascent.
Eat Lunch at the Salt Life Food Shack
Address: 321 A1A Beach Blvd, St. Augustine, FL 32080
You may have worked up an appetite after walking up all those steps at the St. Augustine Lighthouse. Recharge at the Salt Life Food Shack, a popular restaurant and beachgoer favorite.
My main reason to go: obtain a Salt Life car decal. I’ve always wanted this decal, but my husband wasn’t thrilled about the idea. He doesn’t generally like car decals, but this eventually became a silly joke between us.
And I am a beach girl. If I could, I would pack up everything and live the “salt life” with a colorful seaside house on the sand. Having never eaten at Salt Life before, I wanted the sticker purely for what it says.
Unfortunately, that dream of living on the coast isn’t feasible right now, but my eyes lit up when I saw that St. Augustine has a Salt Life. Finally, I could try this popular restaurant and get my decal, which my car proudly displays today (and still very much to my husband’s playful objection).
I wasn’t disappointed with the restaurant either. We sat on the completely outside second floor with a partial ocean view. The food and drinks were delicious – especially the rum runner and the Category 5 cocktail that accurately lives up to its name. I can’t speak for their seafood since I don’t eat it, but the queso and the chicken tenders were appetizing.
Consider These Options For Your Afternoon
After finishing lunch, you can head back downtown or stay on Anastasia Island. I’ve listed below a few options depending on where you want to go or what you prefer to do for the last day of your 3 days in St. Augustine:
If You Stay on Anastasia Island
St. Augustine Alligator Farm Zoological Park
Address: 999 Anastasia Blvd., St. Augustine, FL 32080
General Admission Cost: Adult tickets are $34.99. A ticket for a child (ages 3-11) is $19.99. See additional tickets and discounted rates here. Prices are subject to change.
My father remembers visiting the Alligator Farm in the 1960s with his mom and dad. Back then, it wasn’t as nearly as big as it is today. Kids love the Alligator Farm and will probably make memories that will last a lifetime like my dad did.
The park began in the 1890s as a small exhibit, different from what you see in the present day, a modern zoo with many exhibits: Birds of Africa, Alligator Lagoon, Land of Crocodiles, Pacific Island Reptiles and Birds, Komodo, South American Birds, Lemurs of Madagascar, to name a few.
They have over 20 species of crocodilians, including a massive 15-foot saltwater crocodile named Maximo, his name somewhat reminding me of Maximus from the movie Gladiator. You can even get an aerial view of the zoo with the zip line adventure. Or, if heights don’t bother you, you can scale a climbing wall.
Tickets are a bit pricey but well worth the fun of what you’ll do and see. They are open daily from 9am to 5pm or until 6pm in the summer.
Soak in the Sunshine and Relax at the St. Augustine Beach
It’s the last day of your 3 days in St. Augustine vacation, and you may just want an afternoon to chill, prop up your feet, and relax. I can’t think of a better way to do this than spend the afternoon at St. Augustine Beach.
Besides laying out on the sand or splashing in the saltwater, St. Augustine Beach has other activities, including fishing, surfing, volleyball, bicycle riding, and driving your car on some parts of the beach.
There are many public places to park at St. Augustine Beach. View where to park by clicking here.
Find Nature at Anastasia State Park
Cost: $8 per vehicle (up to 8 people); $4 for single-occupant vehicle; $2 for pedestrian, bicyclist, and extra passengers. Prices are subject to change.
If the weather cooperates and you love nature, consider spending the afternoon at the gorgeous Anastasia State Park.
Walk amongst sand dunes and pristine beaches while admiring several species of birds. More activities include bicycling, hiking, picnicking, fishing, paddling, and surfing. You can even visit the coquina quarry, where coquina was mined to build the Castillo de San Marcos National Monument.
The park is open daily from 8am to sundown and is not too expensive to visit. See additional admission information here.
If You Head Back to Downtown
See Beautiful Stained Glass Windows at Trinity Parish and the Cathedral Basilica of St. Augustine
Address for Trinity Parish: 215 Saint George Street, St. Augustine, FL 32084
Address for Cathedral Basilica of St. Augustine: 38 Cathedral Place, St. Augustine, FL 32084
Located off the Plaza de la Constitución are the Cathedral Basilica of St. Augustine and Trinity Parish churches. Seeing them wasn’t originally on our 3 days in St. Augustine itinerary, but they welcomed us with open doors. And we were immediately awed by the magnificent architecture and colorful stained glass windows that depict biblical stories.
Trinity Parish has a rare Louis Tiffany stained glass and a massive circular stained glass above the front door. You may miss it if you don’t look up. My favorite is the angel that appears headless when looking at the window from the outside in the plaza. The way that the stained glass is made only allows you to view her head from inside the sanctuary. It’s a magnificent piece of glass, but a bit chilling to see it from the outside.
The churches are absolutely worth a stop if they are open and service is not in session. We spent around 30 minutes learning about each church’s history and talking to congregation members. Their love and enthusiasm for their church are evident in how they spoke to us.
Marvel at the Beauty at Huguenot and Tolomato Cemeteries
Address for Tolomato Cemetery: 14 Cordova Street, St. Augustine, FL 32084
Address for Huguenot Cemetery: 3 Cordova Street, St. Augustine, FL 32084
If you visit St. Augustine on the third Saturday of the month, consider doing a free tour of St. Augustine’s oldest cemeteries. These tours give you a glimpse of the life stories of those interred there.
Both cemeteries are gorgeous and peaceful, especially Tolomato Cemetery, the oldest cemetery in St. Augustine. It’s the final resting place for around 1000 people between the 18th century and 1884.
Huguenot Cemetery was a Protestant Cemetery burial ground from 1821 to 1884, and you can find this cemetery north of the Old City Gates.
You can only go inside the cemeteries if it’s a tour, and the two cemeteries are worth a stop as you walk downtown. While there is no charge, donations are greatly appreciated.
The free tours are from 11am to 2pm (the last tour starts at 1:30pm) every third Saturday of the month.
Explore Ponce de Leon’s Fountain of Youth Archaeological Park
Address: 11 Magnolia Avenue, St. Augustine, FL
Cost: An adult ticket is $19.95. Senior ticket (60+) is $17.95. A ticket for a child (age 6-12) is $9.95. Children 5 and under get in free. Prices are subject to change.
At Ponce de Leon’s Fountain of Youth Archaeological Park, you can drink water from a spring discovered in 1513 by early Spanish settlers and Ponce de Leon. The water comes from an underground aquifer containing several minerals, but it definitely isn’t Fiji! I think tasting the water is a once-in-a-lifetime experience. After that, I’m good.
In addition to learning about the early Spanish settlers and sipping the “fountain of youth,” you’ll learn about the Timucua, a group of Native Americans that settled in Florida thousands of years before the Spanish arrived. You’ll see a reconstructed Timucua village showing their way of life, including an anoti, a large family house.
And one of my favorite things is the planetarium show that gives you a glimpse of the night sky when Ponce de Leon’s ships landed off the coast. I think seeing something the way it would have been centuries before is incredible.
Some people might find this place to be a bit touristy, but children and history lovers might have fun exploring. We visited here during our first trip to St. Augustine, and while it was interesting to see, it was probably my least favorite place on the itinerary, but I am happy I still went.
To see the archaeological park, visit their website here for more information.
Have 1950s-style Fried Shrimp at O’steen’s
You might have returned to downtown St. Augustine instead of staying on Anastasia Island. However, if you are okay with the short drive back to Anastasia Island, consider having 1950s-style fried shrimp at the famous O’steen’s Restaurant.
Everyone we spoke with beforehand and in St. Augustine recommended Osteen’s. It’s a smaller restaurant but a favorite among locals and tourists for over 50 years.
And it’s a great way to wrap up an amazing 3 days in St. Augustine!
Where We Stayed During Our 3 Days in St. Augustine
There are many accommodation options in historic downtown St. Augustine and the surrounding area. You’ll probably want to find a hotel or bed & breakfast near or on St. George Street to be close to the major action and attractions.
But to maybe save a little money, consider the surrounding area or St. Augustine Beach on Anastasia Island. We chose the latter and stayed at the Courtyard by Marriott, a few steps from the ocean. The beach is also just a short distance from the heart of downtown – about a 12-minute drive.
From the Locals
We had many recommendations on where to eat or drink from friends living in the surrounding area and from talking to locals we met during our 3 days in St. Augustine. After all, the best way to get to know a place is to talk to the locals!
While we really wanted to try them all, it wasn’t possible during our 3 days in St. Augustine, but if you have extra time or if you want to try something different other than what is listed above, check out these:
In or Near the Heart of Downtown:
River & Fort
River & Fort is a newer southern-inspired restaurant in downtown St. Augustine. They have a rooftop lounge and serve seafood, steaks, cocktails, and more.
Columbia Restaurant
Located on St. George Street, the Spanish-styled Columbia Restaurant serves Spanish and Cuban cuisine at lunch or dinner.
Prohibition Kitchen
This vintage gastropub and lounge were jammed-packed when we walked by it on St. George Street. Prohibition Kitchen’s interior is pretty cool with its industrial-vintage decor and style.
PK’s Roosevelt Room
Right next door to Prohibition Kitchen is their Roosevelt Room. Come here in the morning as they serve a variety of breakfast and brunch items.
Alta Marea
This Tuscan Coast-inspired restaurant serves northern Italian seafood and pasta dishes. Alta Marea is also on the beautiful, historic Aviles Street.
Ice Plant
Go to Ice Plant for a nice dinner. This industrial-style restaurant serves local food and fancy cocktails. Plus, the name of this restaurant is pretty stellar.
The Floridian
We actually tried this modern Southern fare restaurant during our 3 days in St. Augustine. I don’t like to talk negatively about a brand, but I was not a fan of my meal at The Floridian. It could have just been what I ordered, or maybe it was an “off night” for them. Despite my experience, several locals told us to go here because of the fantastic food. Due to this, I am listing this restaurant here so you can decide for yourself!
San Sebastian Winery
We went here on our first trip to St. Augustine and enjoyed their award-winning wines on their open-air deck while listening to live music. The view at San Sebastian is pretty good too.
On Anastasia Island (St. Augustine Beach):
Terra & Acqua
The sister restaurant to Alta Marea, Terra & Acqua also serves northern-Italian food and pizza in a more casual setting.
Osprey Tacos
I love tacos and firmly believe you can’t go wrong with a restaurant that primarily serves tacos. Osprey Tacos’ choices of what they put in their tacos are endless: chicken, soy protein, carne asada, shrimp, pork, tofu, veggies, and chorizo, to name a few.
Blackfly
Located on Anastasia Island near the Bridge of Lions, the Blackfly serves seafood, steaks, veggies, and more. They also have a long list of wines!
Did you find this 3 days in St. Augustine itinerary helpful? If so, please comment and share below!
A Note on My Photos
All images in this article except three photos were shot on 35mm film. Can you guess which three are not on film?
For our 3 days in St. Augustine, I used Atlanta Film Co.’s 250D, 500T, and their newly limited-released Koji 125T. I also used my usual go-to, Portra 400.
I tried the SantaColor 100 color-negative film for fun and experimentation, and I loved the results! See my article SantaColor 100: Bold Reds in Beautiful St. Augustine for more!
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