St. Augustine Road Trip

Our St. Augustine Road Trip to Remember

Well, we’re back in North America, so we decided to rent some wheels and do something we haven’t done in a while…we went on a road trip! And here’s part I of our journey, our St. Augustine road trip.

I love North America for this. Road trips are one of my favorite ways to see different places – and I realize this may sound a little contradictory to my views on cars, but for travel experiences road trips can be amazing memory-filled journeys.

St. Augustine road trip picnicOur road trips always start out the night before though. We do our best Yogi Bear impressions and pack a picnic basket. Oh wait, that’s not right. Yogi STOLE picnic baskets…I guess I made a BooBoo.

We often pack some fruits, maybe some carrots or nuts, and our road trip picnic basket isn’t complete without hard-boiled eggs of some sort. We usually make Egg Salad Sandwiches (one of our favorite minimalist sandwiches), but this go around we had some leftover soup to eat so we packed a thermos the morning we left, along with some boiled eggs for a snack. Mmm, nothing like opening the cooler to release the fart-like smell of hard-boiled eggs!

With lunch packed our St. Augustine road trip was under way, starting with our favorite road-trip game; Tire/Animal. Okay, I think I need to explain this one…While driving to Chicago one year we drove through the middle of Michigan, past Flint and Lansing. I think it was June, so maybe that’s a popular time for deer frolicking, because the shoulders of the interstate had so many dead animal carcasses and blown tire shrapnel from trucks that we could seldom tell the difference between the two until we were right on top of it. So when we’d see some shoulder debris, the first person to correctly shout “TIRE” or “ANIMAL” got a point. We didn’t keep score, there were just too many tire/animals.

After a two hour jaunt we bought tickets for a trolley tour to get around historic St. Augustine, the oldest continuously occupied town in the USA.

St. Augustine Road Trip Stop #1 – JAIL!

We got to walk around a few historic buildings on our first stop, including a Cracker museum, a small “shop”, and I also got to help this Cracker with his gator:

St. Augustine road trip - gator bob


Crackers are the white folk who got their nickname because they could be heard cracking their whips as they rode their covered wagons into town. Little did I know this Cracker above was a little shady, and he somehow double-crossed me so I ended up in the clink!

St. Augustine road trip - St. Augustine Jail


Could have been worse, Shelly must have done something seriously wrong because she ended up on display in the bird cage for all the town to shame her!

St. Augustine road trip - St. Augustine Birdcage


We must have been good role models in the slammer though, because we got set free and resumed our tour.

St. Augustine Road Trip Stop #2 – ALCOHOL!

Doing hard time takes a lot out of ya. Thankfully, the next stop on our tour was the St. Augustine Distillery and yes, we got free samples! The Distillery almost never came to be though. A developer had once purchased the building (and land), but because of the housing market crash of 2008 it never did get developed and just sat there. So some locals pooled some money together and purchased it, later turning it into the distillery that stands today, to our good fortune!

St. Augustine road trip - St. Augustine Distillery

St. Augustine Road Trip Stop #3 – MORE ALCOHOL!

Okay, there are other things to do on this tour, but when you go from sampling some amazing Gin and Vodka and the very next stop is a winery, well…why waste a good buzz, right? We sampled about five wines and one sherry (man I missed sweet sherry, so tasty). The wine-tasting tour is priced just right though – FREE!


St. Augustine road trip - St. Augustine Winery


St. Augustine Road Trip Stop #4 – A SOBERING WALK IN TOWN

In reality, we didn’t drink a lot at all. They’re small samplings, but we wanted to walk around town anyway before driving off into the sunset. The small village was a great opportunity to do so and is filled with shops and old buildings, like the oldest wooden schoolhouse in America. I love this description. I wonder where the oldest brick schoolhouse is, and the oldest concrete schoolhouse, and the oldest metal schoolhouse, or the oldest adobe schoolhouse. Anyway, with many quaint shops and buildings there are plenty of photo-ops. Actually, the entire tour allows for a lot of great photos – I just need a better camera than my phone because you never know when you’ll come across the oldest something in the USA.

St. Augustine road trip - St. Augustine Schoolhouse

St. Augustine Road Trip Stop #5 – THE ROAD TO JACKSONVILLE

Our last stop brought us to our car, where we ate the chicken wraps we packed in our pic-a-nic basket, then set off for a night in Jacksonville – the city of bridges and overpasses. Of course we got lost, but not really. We missed our unmarked exit because of construction but looped back around and found it and our hotel.

If you’re up for a St. Augustine road trip the trolley tour is a great way to see many of the historic sites there. You can easily spend an entire day trolley-ing through town, stopping for lunch, dinner, and to enjoy the many historic sights and stories your driver will assuredly share. Or you can just hang out.

St. Augustine Jail Shackels

Next up…a road trip to Savannah, Georgia

Now go sell all your stuff and take a road trip!

15 thoughts on “Our St. Augustine Road Trip to Remember”

    1. Your trip was a little more on the family friendly side! We didn’t even know about the distillery or winery until the trolley pulled up. That’s why doing a tour like the trolley is an excellent way to find unexpected treats!

  1. Seems like a fun experience. I love road trips as you tend to enjoy a lot more than you would otherwise. There is so much along the way to experience.

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