Last Updated on January 15, 2024

I’ve visited St. Augustine, FL two or three times a year ever since moving to Fernandina Beach, FL, 70 miles north, in 2012. The St. Augustine Alligator Farm could be my favorite tourist attraction in the state. I’ve also visited for art gallery openings, concerts, festivals, to see old friends, and to simply get away for the day.

What is increasingly attracting me there has nothing to do with this – call it the “sunny side” of St. Augustine. Of all Florida, in fact. I’m more and more interested in visiting St. Augustine for the darker aspects of its history, an ugly history most visitors – most St. Augustine and Florida residents even – are completely unaware of.

St. Augustine has layers beneath its touristy Spanish Colonial crust few see, but all would benefit from experiencing.

St. Augustine Arts and Culture

St. Augustine Amphitheatre
St. Augustine Amphitheatre. Photo courtesy FloridasHistoricCoast.com.

Did you know St. Augustine is the best place in Florida to see a concert?

If you ask me, it is.

The 4,000-seat, open-air St. Augustine Amphitheater sits three miles south of the Historic District down A1A on Anastasia Island. I believe Florida is best experienced outdoors, and no venue in the state brings better sound quality and performers to the outdoors than The Amp. Most of the seating is covered thankfully, so events are held rain or shine.

No, you’re not going to see Taylor Swift perform there due to its intimate size, but that intimacy along with its breezy – or sticky, depending on the weather – atmosphere creates a casual vibe perfectly matching the setting. Absent the crowds and mania of arena and stadium shows, but large enough to attract major “name” talent, The Amp is “just right” as a concert venue.

Parking can be tricky. If the small on-site lot is sold out – and if you don’t book fast, it will be – The Amp provides free satellite parking and shuttle service at Anastasia State Park and the R.B. Hunt Elementary School Soccer Field right nearby.

For the first time, instead of making the drive back to Fernandina Beach following a concert at the St. Augustine Amphitheatre, I spent the night a mile and a half up the road at The Local – St. Augustine. This flamingo-pink, 20-room, retro gem regularly appears on USA Today’s list of “Best Roadside Hotels.”

I love quirky hotels. There’s nothing wrong with a Hampton Inn right off the interstate, but given a choice, I’ll always choose the locally-owned, one-off spot with character. The Local’s character is “Old Florida,” that impossible to define aesthetic and feeling each individual traveler associates with her or his or their earliest memories of Florida, be that the 1960s or the early 2000s.

The no-frills Local feels quintessentially Florida-y. It feels like family road trips to Florida in the 80s. It feels like Spring Break in the 90s. At least to me, anyway.

Rates, even on weekends, start in the mid-$100s. I like that. Be aware, its largest bed size is a queen.

The Local - St. Augustine roadside motel
The Local – St. Augustine roadside motel. Photo courtesy of The Local.

Unfortunately, what is most modern about the property, is most problematic. The Local features a totally keyless check-in and room entry system run through an app. There is no traditional front desk or hotel attendant on duty.

I like hotel lobby’s. I like checking in through a person. I don’t like apps.

My first complication with check-in came through how my room was booked online, not by myself, but through my business where I go by a different name than my legal name. When I tried signing in to the app to check in, the room reservation didn’t match my Florida driver’s license the app wanted me to upload a photo of to verify my identity. Fortunately, The Local does send automated text messages on check-in day to guests and I was able to text back and forth with the person monitoring these messages to resolve that problem.

The bigger problem came around 11:30 that night when I was trying to access my room. A Bluetooth connection is required to “download” a digital key to press against the reader on the door to get in. I don’t use Bluetooth on my phone for anything and even though I thought it was enabled on my late-model iPhone, my phone was unable to access the code for entry.

Had my more techy wife not been there with me, I would have been SOL unable to gain access to the room. Remember, there’s no attendant on duty.

My wife also couldn’t figure out why my Bluetooth was unable to secure the code, but she did find a feature on the app allowing my phone to “share” a key with her phone and her Bluetooth was able to access the digital key to secure entry to the room.

Don’t like that.

I’m 48. I don’t mind tech as an option when travelling, but I don’t want it as the only option. I should mention, our Ticketmaster tickets to the concert were also app-only, a common practice now I would have also been unlikely to successfully navigate myself were it not for my wife.

Tech is taking over. I get it. I’m out of touch, I’m a troglodyte, but technology is not a language I naturally speak. I’d rather talk to someone on the phone or in-person. If you’re like me, a word of warning before booking your stay at The Local.

Surrounding The Local up and down busy A1A are a bevy of restaurant choices within a half mile and easily walkable with sidewalks. MOJO Tacos is across the street. There’s a Mellow Mushroom for pizza right nearby. Black Fly is fine dining for seafood.

Don’t miss the large, doughy, reasonably priced pumpkin pancakes at Shelia’s Café / Anastasia Kitchen less than a half mile south on A1A from The Local in the shadow of the St. Augustine Lighthouse. It’s right across the street from the St. Augustine Alligator Farm, meaning the Alligator Farm can be walking distance from the hotel.

The Local does rent bicycles – I like that – but does so via app – GRRR! If you can figure it out (I didn’t try), The Amp and the Historic District are within biking distance from the hotel when the weather cooperates. Biking will save you the hassle of parking which can be a real bear in the typically crowded Historic District.

St. Augustine Black History

St. Augustine, FL was every bit as essential to the Civil Rights Movement as Birmingham, AL or Jackson, MS.

Know this!

In 1964, it was THE epicenter of the Movement.

Know this!

Martin Luther King, Jr. was arrested in St. Augustine.

He was in St. Augustine when the Civil Rights Act was passed by Congress – his life’s work achieved.

Know this!

King described St. Augustine as, “the most lawless city I’ve ever been in,” adding, “I’ve never seen this kind of wide-open violence.”

Know this!

Future mayor of Atlanta and Civil Rights activist Andrew Young was nearly beaten to death by a white mob on the streets of St. Augustine in 1964.

Know this!

The city – and much of Florida during that time – was a hotbed for Klan activity, brutally violent cops, and racist judges.

Know this!

This is the history I’m increasingly being pulled to St. Augustine to learn about. Think about. Feel.

St. Augustine is so pretty with its boats bobbing along the Matanzas River, with Flagler College and its Tiffany stained glass and everything just so, with its undeniably charming Historic District and the boutiques and restaurants. It’s difficult today when visiting to put that out of your mind and go back to within the living memory of many St. Augustine residents and picture this as a vile nest of white supremacy and white terror.

It’s a challenge I encourage you to take on seeing as how Florida, and the nation broadly, is experiencing a backlash against racial equality. A yearning to return to Jim Crow in many quarters. A suppression of voting rights – especially for African Americans – a suppression of free speech and the right to assemble, a suppression of Black history and an understanding of the racism inherent in America. An increase in book bans and neo-Nazi marches. Florida is again the epicenter.

The old Monson Motor Lodge where King was arrested. The steps he was arrested on are still there. The pool where the owner poured acid on African Americans is still there. It’s a Hilton today, but hotel guests can still swim in that very same pool which made the cover of newspapers around the world. The straw that broke the camel’s back. The Civil Rights Act, after having been filibustered more than any other piece of legislation in American history, was passed in Congress the next day.

That’s how important St. Augustine was to the Movement.

Andrew Young Crossing. Lincolnville. Fort Mose.

St. Augustine has a richer story to tell of Black History than any comparably sized city in America.

Know this!

The best way to be introduced to that history on the ground is through one of Bernadette Reeves’ walking tours. That’s how my wife and I did it.

Mrs. B is old school too, so just give her a call at 386-334-3902 to schedule your tour. Only $15 per person, plus tip. She has a five-guest minimum for tours, but if you can’t scrape together companions to meet the threshold, just pick up the difference in cost yourself as my wife and I did and she’s happy to take you out for a 90-minute stroll and chat around town.

Below, I share two podcast episodes smartening visitors up to St. Augustine’s Civil Rights history. The first is from my “Welcome to Florida” podcast and features a Flagler College history professor who will take you through 1964 in St. Augustine and King’s time there and why the city is essential to the Civil Rights story. The second is from Bernadette Reeves’ appearance on “The Florida Spectacular,” providing an audio-only taste of what her walking tours are like.

St. Augustine – the sunny side and ugly side, both deserve your attention.

NOTE: Visitors to St. Augustine from outside of Florida should be aware that the NAACP has issued a travel advisory for the state noting, and warning, that under its current governor, Ron DeSantis, Florida has “engaged in an all-out attack on Black Americans, accurate Black history, voting rights, members of the LGBTQ+ community, immigrants, women’s reproductive rights, and free speech, while simultaneously embracing a culture of fear, bullying, and intimidation by public officials.”

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