A Guide to St. Augustine Florida, the Oldest City in North America: Our Favourites and Photos

I was pleasantly surprised with how “cool” St. Augustine Florida was. It’s not a place I would have necessarily picked to go, if it had have just been Jill and I on a trip. But we were planning a trip to Florida in which Jill’s lovely parents’, Paul and Marilyne, would be joining us. We would spend a few days in Orlando and then do a bit of a road trip to see another part of Florida. When researching options, we decided on St. Augustine Florida as it is the oldest (colonial) city in North America and is on the east coast, so it combines, history which Jill’s folks would like, old stuff for Jill to find in vintage stores, and beaches which we all love.

What we found there was an adorable town, with a walking town centre that dates back to the 1500’s, and includes things like “the oldest school house in the USA” which has to be held together with a large chain encircling the building it is so old. In this walking centre is a bustling area filled with cute stores and eateries and tonnes of live music. And I mean, a lot. You could walk down the street and hear live music pouring out of buildings. But overall, there was just a “cool” vibe; there were plenty of young interesting people working, hip stores, and a vibrant art and music scene.

It is undoubtedly a tourist hub, although not too busy in February. It didn’t have that “overrun touristy” feel, if you know what I mean. There are lots of stores for the tourists to peruse, but they aren’t just tourist knick-knacks and cheap crap stores. In a nut shell, for a tourist destination it felt remarkably authentic.

We all 4 enjoyed our time in St. Augustine, and could have easily spent another day or two here. There is a lot to do in St. Augustine Florida and its surrounding areas, and beaches. This place would be glorious, although probably very busy, in the summer when the beaches are in full swing.

St. Augustine Florida: a city full of history

St. Augustine has a long and dramatic history that includes, colonization, fighting between the Spanish and French, pirate attacks, a central role in the Underground Railway to help for slaves, and a holiday destination.

According to the St. Augustine’s website on the city’s history, Florida was “discovered” in 1513 by the first governor of Puerto Rico who was on an exploration. He claimed Florida for the Spanish Crown and named it Florida “aka Easter” because he discovered it around Easter.

The St. Augustine website says :

“Founded in 1565, St. Augustine is the oldest continuously occupied settlement of European and African-American origin in the United States. Forty-two years before the English colonized Jamestown and fifty-five years before the Pilgrims landed at Plymouth Rock, the Spanish established at St. Augustine this nation’s first enduring settlement.”

At this juncture, I do need to acknowledge that, like all of what is now known as North America, these lands were not empty before the Spanish “discovered” them. North American’s indigenous/ aboriginal/ First Nation’s populations roamed and settled all over North America. As is the case with all of North America, these populations were colonized as Spanish, French, English etc began claiming lands other than the territories from which they came, as their own, often with force and violence. St. Augustine was the first official “city” of the USA, but the people who founded St. Augustine were not the first people to discover this area; the First Nations people were there first. St. Augustine therefore, is the first place to be named an “official” city in the USA.

For more on the history check out the St. Augustine city webpage.

Our Favourites for St. Augustine Florida

Favourite piece of history:

St. Augustine was a sanctuary for slaves. The first Underground Railroad to help enslaved Black people escape to freedom was centred in St. Augustine Florida. Pretty cool, St. Augustine, pretty cool.

From the St. Augustine Florida city website:

“British attacks continued [on St. Augustine]. Plantation and slave owners in the English colonies resented the sanctuary that Spanish Florida afforded escaped slaves who successfully made their way to St. Augustine, which became a focal point for the first Underground Railroad. There, escaped slaves were given their freedom by the Spanish Governor if they declared allegiance to the King of Spain and embraced the Catholic religion. In 1738 the first legally sanctioned free community of former slaves, Gracia Real de Santa Teresa de Mose, was established as part of the presidio’s northern defenses.”

For an interesting article by Rosalind Bentley from the New York Times on the sites in Florida where the Underground Railway was run, click here.

Place to stay:

We stayed at the Florida Motel, which was one of the highlights of our trip. Goodness this place is adorable and wonderful. It is a little mid-century motel, that has been revamped into a stylish, hip little place that still holds on to the nostalgia of its era. Look for it on Airbnb.

We stayed in a self-contained 2-bedroom duplex, which was part of the re-vamped little pink Florida Motel (click here for the place we stayed). It was soooooo cute, clean and sweet. They also have free bikes to use, which we loved and made full use of, as it is 3 km out of downtown. Bikes are a perfect way to get around St. Augustine Florida.

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Favourite places we ate at:

Dinner: The Floridian

In their own words:

WE CALL IT ‘INNOVATIVE SOUTHERN FARE FOR OMNIVORES, HERBIVORES AND LOCAVORES.’ REGIONALLY-INSPIRED AND FRESH FROM THE SOURCE, OUR CUISINE IS A SYNTHESIS OF DOWN-HOME SOUTHERN COMFORT FOODS, AND LIGHTER, HEALTHIER, VIBRANT AND CREATIVE DISHES–WITH MANY VEGETARIAN OPTIONS.

The place had a lovely hip but comfortable ambiance and the food was fantastic. It is located on Spanish Street, which is one street over from the main drag in the old town.

Desert: Hooked on Harry’s

The Deep Fried Oreos were to die for. We went back twice. The other wonderful bonus about Harry’s is there is nightly live music on their beautiful outdoor patio. All of the food we tried there was very good. This is a great dinner option as well, that hails itself as a New Orlean’s style sea food bar and grill. Definitely worth checking out.

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Best drinking idea

I have never seen a place like Auggie’s Draft Room. And what a great idea. You get your beer cup and it is attached to your bill/credit card, and then you fill it how ever much you want and each time you fill it the price per ounce for the amount you take is charged to you.

I took the approach that I would try each and every one with a sipper. Jill took the approach of just picking her two most likely favourites. For the non-beer drinker, there are a couple wines on tap as well.

I’m not sure why my home town doesn’t have such a thing! What a great idea.

Favourite in-town activity:

Strolling through St. Augustine’s old town area, checking out stores, listening to music, eating ice cream, drinking beer is just a good time.

The old-town area is chock full of little stores, ice crème shops, restuarants, and live music venues. In the day and the evening live music could be heard pouring out of places. St. Augustine was lively, remarkably hip for a tourist destination, and full of history and personality. 

Best shopping

There is an area just north of the old town centre where there is a clump of vintage, consignment and thrift stores on San Marco Avenue.

There are 4 great vintage shops, a used books store, and an ice cream store in this little half block:

• Cool and Collected, was just pure awesome fun, with a number of colourful fun rooms to walk through (the photos are from here);
• The Way We Were Vintage, which was large with a wide selection on sellers and range if items for all eras- great store to roam about in for treasures;
• Antiques & Things;
• A Step Back In Time;
• Anastasia Used Books.

Further north of town another kilometre or so (near the Florida Hotel), on the same street is a large thrift store as well. Although we did not find anything too great there, you never know.

Best venues for live music:

The coolest thing about St. Augustine Florida might just be the amount of live music venues. Here are just a few we thought rocked:

Prohibition Kitchen

They have their menu as well as their Live Music Calendar online.

In their words:

“Deep in the heart of America’s oldest city, a vintage gastropub and lounge is being born.  Invoking the spirit of Bartolo, who on this very spot created “Genovar Theater”, the social epicenter of Flagler’s prohibition era… we offer you an escape into the clandestine, mysterious, and yes, illegal world of flapper dresses, speakeasies, moonshine, and swing.  Sashay in and let your senses be seduced.  Let chef Bradford’s seasonally inspired techniques using local ingredients put the exclamation point on your rendezvous back in time… experience the Prohibition Kitchen.“

Hooked on Harry’s

In their own words:

“Overlooking the beautiful bay front in historic downtown St. Augustine, Harry’s is the perfect place to relax and listen to the nightly live music in our legendary courtyard.”

(Courtyard pictured above).

Colonial Oak Music Park

In their own words:

“The Colonial Oak Music Park is a unique downtown venue for live music and shows. A beautiful old live oak spreads its branches over the seating area, keeping guests cool and also enveloping them in a nostalgic old Florida atmosphere. The intimate stage and setting feature family-style table seating for more than 250 visitors. “

The guy on the buckets

You could hear this street performer long before you saw him. It sounded like a band. You walk around a corner and all that is there is this one guy and some buckets. He was amazing. Check out this short clip:

His sign says:

“Tips keep my dream alive”.

@marks_bucket_beats

So shout out to @marks_bucket_beats who you can follow on Instagram.

Favourite outdoorsy activity:

Biking about the city is perfect.

Even though Marilyne had not ridden a bike in about 20 years, Jill, Marilyne and I checked out the town for the day on the free bikes from the Florida Hotel.

Instead, Paul took his borrowed bike and went on a 64-mile (return) ride up the coast on the bike path that lines the coastal A1A road, which is lined with a bike path. Talk about motivation! He said it was a good ride, and we believe him.

What I wish we had have had more time to do:

Go to Anastasia State Park and watch the surfers (or go surfing yourself). Rumor has it that the best surf spot around is past the Blowhole in Anastasia State Park, which is in St. Augustine Beach area. St. Augustine Florida

It was February and a bit chilly when we were there, and the beaches were quite blustery and cold. So we didn’t prioritize beaching as much as I had thought we would. I had anticipated that it would be warmer in Florida this time of year, but it was generally well under 20 degrees celcius- not beach weather; rather it was long sleeve weather mostly.

There are also lots of tourist activities to partake in. These aren’t really our thing, but they get rave reviews so may be worth checking out:

• The trolley tours, by Old Town Trolley and by Ripley’s Believe it or Not Red Train;

• The Old Jail

• Castillo de San Marco, the oldest Fort in North America and a national monument. We took a walk around the outside of the Fort and checked it out. While the fort is pretty neat, as it is very old and has a moat, the walk around the outside was enough for us. But you can pay to go inside as well.

For more information and details on these sites, and other things to do in St. Augustine Florida check out the Visit St. Augustine webpage.

Summary: St. Augustine Florida

St. Augustine was more than I expected, in a number of ways. It was cool, hip, active, fun, musical and just totally enjoyable for people of all ages.

This post is part of Beyond the Gaybourhood’s FLORIDA SERIES. For more information on Florida, including information on what to do in Orlando, theme parks, a road trip up the Coastal A1A, St. Augustine, and hiking the Florida Trail in the Ocala National Forest, read my blog post “Orlando and Beyond: Florida Road Trip”.

Orlando and Beyond: Florida Road Trip