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3 days in St Augustine | The Ultimate Agenda

St Augustine is a city mixed with a rich history, amazing food, culture and no shortage of things to experience. It’s a welcoming old-world, inviting and a little magical. It feels like you have stepped into an ancient European city while enjoying the luxuries of amazing modern cuisine and fun! It’s truly a uniquely charming place that I fell in love with instantly, and I have a feeling you will too. This agenda is for those who want a little more than just casual afternoon strolls, with a focus on food, adventure, and the city’s story.

St Augustine has so much to see and do - from amazing food to really interesting history and amazing sunhine! Here's the Ultimate Guide to a 3 day vacation in America's Oldest City - with food stops, outdoor ideas, and must-see Instagram worthy spots!
A trip to St Augustine is a battle between just how to spend your time! There’s so much to do and see!

I am grateful to St Augustine Historic Florida Coast for my time exploring the historic city. Thoughts and opinions are my own. 

There’s an infusion of history, culture, and local pride that you can immediately sense when you first arrive in St. Augustine. First established in 1565, along the protected shores of the Matanzas River on the Atlantic Coast of Florida, it is one of America’s oldest cities that stands as a walking museum rich with pristine architecture from every era since it’s conception.

After initial Spanish conquests and revolutionary holding swaps, the area became central to the luxury of the vacationing land lust for railroad tycoons and after that a hotbed for the civil rights movement. And all of this can be seen engraved in the sidewalks and memorable construction in less than a 4-mile stroll through the coastal downtown.  

The courtyards and public areas around St Augustine are totally inviting!
Because we all need to see courtyards this pretty everywhere we go!

St Augustine feels rich with fascinating stories while it holds true to it’s colorful roots even to a new wayfarer. The city feels alive and rooted like strolling through seaside villages in Europe with the bricks padding the narrow streets. There is a sense that the locals understand the mystical beauty captured by such a timeless place as they beam with pride at their modern-day entrepreneurial pursuits.

From shopkeepers to innkeepers, young restauranteurs returning to the city of their alma mater, and visionaries establishing new business models, the city is alive with a flow and rhythm that is enchanting all it’s own. Not like a tourist destination, hidden behind the bubble of its signature time period, St Augustine shines with a light from a special place under the surface, and it radiates outward welcoming all those who step through the 400-year-old wooden gates.

I decided to discover as MUCH as I could in my quick time here. There is honestly, so much more to see and do than one can realistically fit into a few days. Which is great, because this is a place I would come back to again and again! And for someone like me, who travels all of the time – that says a lot!

On the other side of town sits the working docks for the local shrimp boats

History and Fun Facts

St. Augustine was first established in 1565 and kind of had a few (hundred) years of incredible significance as it built its legendary roots with native conflict and iconic pirates like Sir Francis Drake coming to ransack the city. It spent the next few centuries with several notable sieges that took place as the Americas were established.

St Augustine has rich cultures from it’s obvious Spanish influence to housing the first free Black settlement in the 1700s at Fort Moses and playing a pivotal role for African American history with the original Underground Railroad leading many individuals to the city. 

There is also a rich Minorcan history flowing through the city as well, who were the indentured labor force from the areas along the coasts of Greece, Italy, and Minorca. After fleeing to the city of St Augustine the few remaining survivors set up homes and their rich heritage and amazing foods live on in modern eateries throughout the city. 

However, it doesn’t rise as the tourist designation it is today until oil tycoon Henry Flagner decided to build a luxury hotel catering to the wealthy in the center of town. With opulent design and no detail overlooked in the design, it drew the rich and famous for the winter season to the humid Floridian climate. 

In the 1960’s St Augustine became a hotbed for the civil rights movement, though it had been known for political activism since the establishment of Lincolnville post the emancipation proclamation. Heroes of the civil rights movement were beaten and arrested in the streets of St Augustine and rabbis stood to defend them as they paved the way for what would be a turning point in our country’s history and the Civil Rights Act. 

It’s also a noteworthy spot for literary dreamers to spend hours dreaming up their next pages with the likes of Hemmingway and Hurston making spots in the narrow streets.

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Now St Augustine sits as a bustling tourist town, locked into historic architecture, beaming with the best holiday lights spectacular in the Nation, and overflowing with an homage to its multicultural roots as the Oldest City in America. 

Colonial Oaks gathering area hosts live music weekly and connect to - you guessed it - the bars!
Anyone want to catch a show?

When To Visit

St Augustine is like any coastal Florida city, more enjoyable from in the cooler months from September to May. However, the coastline is stunning all year long and there is always something going on. With a variety of festivals, there are no shortages of reasons to venture down. 

From the Sing Out Loud Festival with free music all over the city, races, fireworks, historic reenactments, to the millions of dazzling lights that line the city for the Nights of Lights from December through January there are major events every month worth marking your calendar for.

Where to Stay

There is no shortage of places to pick when planning a stay. From top level historic resorts like the Casa Monica Resort and Spa to the dozens of modern Inns speckled around the city and even quite a few campgrounds for traditional tent camping or RV parking along with all the traditional trusted hotel chains if you are a points guy. 

I stayed in one of the recently remodeled suites at the St George Inn, with views of the Castillo De San Marcos. The rooms are hosted throughout a small section of town above shops and courtyards for sipping wine and enjoying coffee.

Every morning they offer a continental breakfast of yogurts, fruits, cheese, meats, and pastries. As well as hot coffee and tea.
In the evening they have a wine bar with hand-selected wines chosen by their amazing staff and connoisseurs at Bin 39.

Bin 39 - Wine bar at St George Inn. Perfect to sit and relax.
Perfect nook for morning coffee or afternoon sangria!

Although the rooms are above the bustling courtyard, they are quiet and absolutely cozy with soft beds and beautiful high tiled showers. Each room has a TV, mini-fridge, and coffee machine as well. 

There are 25 rooms on the property and they start at $209.00. Be sure to check the website for special offers. 

St Augustine at sunsets is one of the pretties cities to stroll through as the pastel skies paint the narrow streets and historic facads.
Fun Fact: St Augustine’s narrow streets are lined with thousands of BRICKS – not cobblestones.

How to Get to St Augustine and getting around their narrow streets: 

If traveling from out of state, the easiest airport to fly into is Jacksonville. It is a quick hour-long drive on the road to the famous city. 

From Orlando or central Florida, St Augustine is a just under a 2-hour drive along I95. 

St Augustine is possibly the most walkable city I have ever explored with paths along the waterfront and all the way through to the winery. I spent most of my time exploring by foot. There are some older brick roads to be cautious of if you are prone to ankle issues but otherwise, the sidewalks are great. 

You will need a car if exploring the beaches and other outlying spots like the lighthouse or National Parks. Though, there is a trolley that does run from the beaches to the town and is a great option if you are a savvy planner. 

3 Days in St Augustine Food, History & Adventure Itinerary:

Day 1: 

Arrive. Check-in at St George is as early as noon as they will accommodate arrival times if you coordinate with them. 

Get your bearings and explore the city by trolley. St Augustine has a LOT of history, cool museums, funky facts and things to see. Spend an hour just enjoying the views and getting a feel for where you would like to visit with Old Town Trolley Tours. The tours have incredibly well-versed drivers who tell you short snippets about all of the major stops, and even a few fun facts in between. There are a bunch of trolley stops all through the town, that allows you to pop on and off.

But, do the full loop first – I know it’s hard! But you won’t be able to see and do everything in St Augustine in a short visit, so this is a great way to learn about everything with entertaining drivers! Once you do the full loop, you can pop on and off for the full day. No need to really drive anywhere at all today! 

St Augustine Seafood Co prides themselves on fresh local seafood - and batters it up to perfectly delightful bites!
You bet I’d wear that.

Lunch: 

Stop at for Lunch at St Augustine Seafood Company. Right on St. George street is a series of great little spots to eat. Actually, a lot of spots to eat. Picking one can be hard, but the St Augustine Seafood Co makes a pretty good bid for the top of the list with fresh seafood, with local clam chowder, fried fish sandwiches and shrimp – delicious shrimp with datil pepper dipping sauce, it’s a fun mouthwatering lunch that won’t take up too much of the day. And it’s right in the center of all the action. 

It's hard to pick just one thing to try at St Aug Seafood Co - the clam chowder was absolutely amazing tho!

Spend the rest of the day taking advantage of your trolley pass, and walk through a historic village at Colonial Quarter where you get a quick overview of St Augustine’s history, and if you are super lucky they may even let you fire a canon (I did – and I honestly don’t know if I was lucky or if they knew I was writing this, but also, I GOT TO FIRE A CANON. So yay. I mean, obviously, it wasn’t loaded and there was a very well educated and safety cautious expert standing right next to me guiding me through the one step I was actually managing – but still, canon). 

Watching this master blacksmith work a hot piece of iron has me mesmerized!

Tip: If you explore the Colonial Quarter before lunch you get a discount for your lunch at the St Augustine Seafood Co and a few other restaurants. 

While on St George Street, visit the St. Photios Greek Orthodox National Shrine for the first colony of Greeks to the region and their story since, then walk a little further and step in the footprints of Andrew Young at the central plaza, pausing to read his values, and then venture a little further into the Lincolnville Museum for an important education of the community, the region’s history as one of the first free settlements, African American history and culture. 

This simple path had such an impact as I followed the footsteps of Andrew Young
This may be one of the most thoughtful memorials I have seen. With simple footsteps and values inscribed so we may know who helped pave the future for equality.

Remember, you can always pop on and off that trolly to help you get to all these amazing places.  

La Floridian was one of my favorite dinner spots!

Dinner: 

Relax and enjoy dinner at La Floridian. This restaurant is a blend of amazing dishes, local love, vegan options, and amazing cocktails. So in a nutshell, exactly where you want to be. However, because it’s so darn good, it fills up quickly, so be prepared to wait. And seriously, it’s worth the wait. Also, you will want to save room for dessert (a trend you will notice on this trip).

Outdoor dining at La Floridian
Please tell me I am not the only one who thinks this is a magical little spot!

Day 2: 

St Augustine isn’t just strolling through beautifully preserved historic streets. Just a bit out of the main historic city, get your heart pumping with adrenaline. Spend a morning playing outside by challenging yourself to a high ropes course over alligators! Listed as a zipline, the course at Alligator Farm is an interactive ropes course with a lot of ziplines, with self-guided challenges designed to make you work.

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For ages 8 and up, there is something here to test everyone. The action has you zooming above the hungry snapping jaws of the alligators and crocodiles as well as near a few exotic birds and lemurs for a truly uncommon view of a zoo. Luckily there are platforms with frequent water stations to pause in between sections. 

Good to Know: You are not permitted to carry your phone or camera with you – as anything that could fall and endanger the animals is prohibited. Bring a GoPro and harness if you want to capture the adventure.

Iced coffee at Good Karma Cafe was a must while visitng the food truck village
Grabbed an iced coffee – because I also may have taste tested 5 or 6 coffee shops while in town…

Pop into the Village Garden Food Truck park and check out what’s fresh at Big Island Bowls or coming off the smoker at Riptide BBQ before grabbing a cold coffee at Good Karma Cafe. The trucks rotate daily – so expect to be surprised! Or you can stalk their calendar to see who’s there, but where’s the fun in that. 

Reflection of the sky in the smooth waters of Anastasia state park beach
Fun Fact: See a hole while walking to your beach spot? That’s the home of the Anastasia Island beach mouse! This is the only place you will find them in the world.

Soak up the sunshine at Anastasia State Park. There are trails to walk, beaches to play on. Kayaks to rent. This truly is an afternoon where you can enjoy pristine white sand, soft beach grasses and wonder about the local tortoise population as they graze nearby. However, you enjoy a ‘beach day’ this spot is great.

Oh Rnger! Free Wifi at the state parks
I took this photo because “Oh, Ranger!” cracked me up.
gopher tortoise strolling along and nibbling at Anastasia beach
Hmmm, I think I’ve seen your cousins on the other side of the state 😉

There are bathrooms near the beach access with rinse stations to wash the sand off before heading back to the car and wifi is even provided at the cafe and shop.  

Dinner: 

Refuel after the long day at Catch 27 with an amazing seafood dinner. Designed to elevate the abundance of fresh seafood from the coast of Florida, the menu is stocked with light expertly prepared seafood all as locally sourced as possible and served fresh. There is a craft cocktail menu, appetizers, and main dishes to pick from with options to sit outdoors on the secluded patio or inside. 

Trust me, try the deviled eggs at Catch 27!
If you don’t try the deviled eggs while at Catch 27 you have missed a true delight of your time here.

From Catch 27, you can walk to many of the local hotels or catch an inexpensive ride in the local luxury golf cart and tour taxi, Explore Tours, which starts at $4, a total bargain! There is a lot of live music and little nooks to stop and check out if you feel like an evening stroll along the streets, tho. 

Day 3 

Visit 2 National Parks (or even 3). Hard to miss, sitting right on the Matanzas is the Castillo de San Marcos National Park. You can walk around the park for free, seeing the fort from outside of the walls, and there are paths leading right up to it.

Imagine what it must have been like looking out over the bay while patroling the Castillo de San Marcos!

To enter, there is a fee to the National Park System, of $15.00. Children under 15 are free.  Each room in the fort is designed to highlight certain stories from its long history as well as local culture and iconic individuals.

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There are daily performances daily reenacting life in the Castillo that engage with visitors. The park allows you to climb the steps to the wide upper area to look out over the canons, to the water, with plaques explaining key moments and how the fort was built. 

Fort Matanzas sits over there on the horizon
This inlet is also great for paddle boarding and fishing!

Just a few miles down the road, sits the Fort Matanzas National Park, however, as of my visit in winter of 2019, the dock was still under repair from damage and the free fairy to and from the fort was not taking passengers. There is a small area explaining the fort’s past, with a video room, and picnic area tho. 

For bonus points, you could make time to stop at Fort Carolyn on your way back to the airport, at Timucuan Ecological & Historic Preserve

Lunch: 

Enjoy Peruvian cuisine at Llama for lunch. Sitting right off highway A1A is the small unassuming spot named after Peru’s favorite animal. The lunch menu is small, and that is good because you will want to enjoy all of it! The fresh juices are amazing and the burger may go down as my best burger of 2019, and that’s saying a lot from the girl that owns burgermonth.com. Ask about the daily soup before settling into your decisions tho. 

We were surprised with this dessert by the owner of Llama, what really made it magic was the attention to detail.
The attention to detail on this plate was very special to me – it was modeled after the Sacred Valley in Peru – a beauty I have seen first hand when I visited.

You won’t want to miss touring the grand opulence of Flagler College, once the immaculate Hotel Ponce de Leon. Tours run while students bustle around you as a student guide leads you through several main areas in the central building and outlines the details of the building and the impact of Henry Flagler on the city as he picked the spot for his grandiose hotel. 

The entry to Flagler College
After my time here, I am reading Flagler biographies to see just how he did it all.

The tour is an hour long and really shines a great light on the buildings’ past and how it operates today as a unique college. 

Right across the street is the Lightner Museum, a collection of 19th-century art, from paintings to sculptures, taxidermy, and artifacts. It sits inside the Alcazar Hotel, also by Flagler, and you can still dine in the luxurious massive indoor swimming pool, now drained, and home to a cafe. This is a self-guided tour and you can stroll as long as you enjoy.  

The Lightner Museum looks like it's out of a movie with the beautiful Nights of Lights display in December and January
Seriously, St Augustine is just showing off now.

Authors Note: If you are short on time and must choose, I found the tour of the Hotel Ponce de Leon unexpectedly captivating. I would never force a choice between enjoying a priceless collection of fine art or a tour, however, the building is art itself and the oral history given by a student is a really fun experience. 

Dinner: 

Dine at a local staple, the Raintree. No detail is overlooked in this timeless establishment. With a menu that reads of old school formal dining tradition, the delicious classic meals, like Beef Wellington or rack of lamb, come with soup or salad and are served with daily vegetables. The staff is expertly trained to attend to you and the ambiance holds the character of the Raintree together. Save room and order the crepes. Trust me. 

Massive berry filled crepes you do NOT want to miss at the Raintree restaurant

Tip from the locals: 

Be sure to stop by the Saint Augustine Amphitheatre on Saturdays to check out the local produce and beautiful wares at the weekly farmers market. Or, really explore a fun outdoor market on the 2nd and 4th Tuesday of the month at the Nightmarket! There is even live music, food trucks, and concessions to really make a full evening of it. Otherwise, be sure to check if anyone is playing! It’s a wonderful smaller venue with great shows. 

If you happen to be in town during one of the Urban Asado pop up dinners – don’t even think, grab a ticket! Or heck, plan a trip just so you can attend. These dinners are a wonderful collaboration between Urban Asado, showing off their amazing asado style grills and Chef Michael Lugo leading the Chefs Collaborative, where 3 to 4 talented local chefs arrive to create a fresh and over the top menu together cooked over the flames.  

View of the cafe that now sits in the grand pool of the Alcazar Hotel.
I would have loved to have seen this when they flooded the pool and let the Great Gatsby style party commence.

What to Pack

The weather is usually pretty balanced, but it’s smart to be prepared

  • Light Jacket or Sweater
  • Sandles
  • Umbrella and/or Rain Coat
  • Comfortable Walking Shoes
  • Nice Slacks or Dress
  • Casual Beachy Clothing
  • Swimsuit
  • Open Toed Shoes if considering the zipline adventure
The historic gates of the city welcome you and remind you just how old she is.

Ready to plan a trip to St Augustine?

Be sure to read more about the historic highlights, fine dining and ghost tours on AskChefDennis.com or more about the gourmand delights at ShesCookin.com.

If you’ve enjoyed this travel review or any other adventures on Pass The sushi, let me know where you found us in the comments below, I love hearing from you! Be sure to check out my other fun travel tips and follow along on Instagram @passthesushi & @girlcarnivoreTwitter Facebook.

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Christina

Sunday 26th of January 2020

Your photos are beautiful! Thank you for sharing your itinerary. I would love to take my time visiting so I could spend time on the history and time on the beauty of the location.

Trisha

Tuesday 21st of January 2020

We are headed to Florida the end of February. I might have to add this to our list of places to stop. Thank you for sharing!

Amanda

Monday 20th of January 2020

Of all the times I have visited and lived in FL, I have yet to visit St. Augustine. I will have to make a special point to get there this year. It is beautiful!

Taci- Life Beyond Zebra

Sunday 19th of January 2020

Looks like a cool place. I have been seeing a lot of Florida lately, really interesting there is more there than meets the eye for sure.

heather jandrue

Sunday 19th of January 2020

This is the 3rd article I have read about this city. It is quite a popular place. I will have to give it more consideration.

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