The Travel Dispatch

Accidentally (Ok So Purposely) Sneaking Into The Pensacola Historic Village

This post was born 31 Dec, 2014 9 Comments
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I’m not a criminal.


Did I do a criminal-like thing?

Absolutely not.

Well, ok…maybe.

Kind of.

I mean does trespassing in a neighborhood that’s been around since the 1500’s really count as a crime? I don’t think it should. It’s survived this long so surely it can handle lil ole me stumbling in afterhours.

Well, ok so I guess I didn’t exactly ‘stumble’ since there was the matter of a fence. Which admittedly stood for the sole purpose of keeping intruders (that’s a harsh word to call me right?) out. OK so yeah, maybe crossing the threshold on purpose constitutes a crime in some states. And yeah so I’m probably lucky that none of the this-town-is-so-small-I-have-nothing-better-to-do cops didn’t cruise by looking for delinquents like me.

So, Ok. Fine. Whatever. I committed a ‘crime’. But clearly it wasn’t my fault. The blame entirely lies in the jumbled hybrid mix of my mother, local beer, elementary school, my ancestors, a poor guardsmen, and a heavy dose of nostalgia.

Pensacola Bay Brewery
Mainly their fault…thanks mom

Perhaps I should start at the beginning…

It all started on a rather crappy Sunday in my hometown of Gulf Breeze, Fl. My mom and I were doing what we do best – eating and drinking across the bridge in Pensacola at every place we could possibly fit in in 1 day. I already shared with you how downtown suddenly decided to become cool the minute I moved away (figures) and since I only visit home once a year, we thought it would be fun to experience everything the newly built up area had to offer (though we were severely punished for an overindulgence of ‘fun’ the next morning – long gone are those college days when hangovers remained an elusive mystery).

My younger cousin, Kevyn (whose awesomeness outweighs mine tenfold) is always up for daytime shenanigans so it was only natural that she would accompany us. We had begun with bottomless champagne at The Fish House, continued on with BBQ and beers at the new Al Fresco food truck area, and then veered off Main St over to Zaragoza to swing by the Pensacola Bay Brewery for some locally made IPA’s.

This is the moment the initial seed (which would grow out of innocent endeavors into a fully blossomed misdemeanor) was planted. You see, to get to the Brewery you must walk through the old town square and pass the T.T. Wentworth Museum which is when my childhood nostalgia took hold. It was my absolute favorite museum as a kid and many elementary school field trips were spent there marveling at the shrunken heads and mummified cat on display. Not to mention, I won numerous battles over the other students to which the prize was getting to play Weatherwoman up on the top floor. It had a green screen and everything which was all a 9 year old kid in the 90’s could ask for.

TT Wentworth Museum

As I was wondering aloud to my cousin as to whether or not the museum still exhibited the shrunken heads, we entered Historic Pensacola. Old cottages lined both sides of the street proudly displaying their badges of honor inscribed with their name, the year they were built, and in some cases their historic significance. Many are still in use to this day and house everything from music schools to quaint shops and art galleries.

Then there’s the enclosed section where I once again wistfully reminisced on childhood days spent learning about our local history which involved hands on educational tours that taught us the simple domestic skills used in the 1800’s such as churning butter and making soap. Let us also not forget the industrial boom commemorated in Pensacola’s Historic Village by the original train cars out front. That’s what did it. There is just something about train cars that screams “I JUST WANT TO PLAY ON THEM’. The seed had taken root in my childish brain and I wanted back behind that fence whether it was closed or not.

Still, it was just a measly little thought that I had no intention of actually acting on. All was forgotten (for the moment at least) when we walked into the packed Brewery for our DeLuna Kolsch. We chatted, drank more, said hi to some people we knew because heaven forbid you go anywhere in Pensacola without running into someone you know.

When it was time to move on, well, I’m not exactly sure how to explain what happened next. Maybe it was one of those creepy mind communication tricks where all 3 of us just looked at each other and had the same singular thought. Or maybe it was the magnetic power of the trains? Or the influence of our ancestral ghosts? It’s all a blur but the next thing I know, we’re back outside and my mom and I are trying to propel my cousin (full on cheerleading style) up over the fence.

Which unfortunately proved a bit too high as she was almost impaled upon its spikes (sorry Kev). We were about ready to give up until we noticed the fence a block over was a bit lower and definitely scalable. Luckily for us, it didn’t come to that, for as we checked all the gates along the way, we found a weakness. Someone had absentmindedly forgotten to lock the latch (oops). Voila! We were in.

My cousin is so mischievous

So like any mature 23, 27, and 54 year old would do, we made a beeline straight towards the early 1900’s Baldwin Steam Locomotive Train and Caboose in front of the Museum of Industry.

Where we did a little dance…

Pensacola Village

Made a little love…

Pensacola Trains

And basically got down (or rather up) tonight…

Pensacola Trains

Since we are definitely the dorkiest felons around with a genuine interest in our historical heritage, we didn’t take this break-in opportunity for granted. We visited Julee Cottage which has been around since 1805 and was home to a noted freewoman of color. It celebrates Pensacola’s Black history and heritage with an interior collection of various home items showing what local life was like for the Black communities during the Reconstruction Period. Since we didn’t want to add breaking and entering to our ever growing rap sheet, we were unable to see the interior exhibit so we walked the perimeter of the house and admired its Salt-box architecture.

We continued to pay homage to this 450 year old town by strolling around and taking in various architectural elements celebrating different time periods such as the French Creole Charles Lavalle House and the Victorian era Lear-Rocheblave House. We also passed by one of the oldest churches in Florida and discovered a well dating back to 1770. By this point, we didn’t want to push our luck any farther as the bored cops were bound to pass by sooner or later so we thought it best to continue back  towards the main strip on Palafox St to meet my aunt for more pub crawling. But of course we couldn’t resist playing on the cannons along the way…

pensacola canon
2 peas in a pod

For full tour and visitor information (during opening hours of course!!) visit Pensacola Historic Village’s main website. All tours are under $10.

My guilty conscious caught up with me so afterwards I went and made a donation! 

For a comprehensive list of things to do in Downtown Pensacola click here.

Have you ever snuck into a historical site? Have any cool areas like this in your hometown? Let me know in the comments below!

Why Suffer From FOMO When You Don’t Have To?

Taking on the classic “round-the-world” route, the next Travel Dispatch journey kicks off Nov 15 as I travel east to west, looping the globe over a period of 12 months with $25,000. Now’s your chance to get in on it from the very beginning!

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9 Comments on "Accidentally (Ok So Purposely) Sneaking Into The Pensacola Historic Village"

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Snarky Momma With

Ahhh, you rascally delinquent, you. It was worth getting caught just for the pictures. The history lesson was pretty cool also. Great post. I bet you could have gotten a Go Fund me for bail off of this post if you had needed it!


Love this post!!! So well written!!!! Keep ’em coming!


This was an awesome story! I can’t say I have ever snuck into an historical site before, but I have done my fair share of sneaking in places. Most of them also involve my mother, as she is the one who taught me to just pretend like you belong and no one will question you! My most recent sneaking involved a little curtain shimmying and back hall walking to get to the holding rooms for celebrity speakers at a conference. Hello hanging out with Amy Poehler and Martin Short- thanks mom!

Stephen & Jess

What an awesome post – looks like you had a lot of fun, love visiting historic places.


Sneaking into a historical village..? Well, ok 😀 Good you made the donation afterwards. I guess every now and then, each of us needs to taste the forbidden fruit, right 😀


You sneaky things! It looks fascinating though, I’m a huge history geek so I’d probably have done the same!


Now these are the types of adventures I love: spontaneous and maybe a little daring!