First Florida Expedition: St. Augustine

My husband and I love road trips. We loved driving my old Yaris to Keels & King’s Cove in the summers and his old Jeep to Humber Valley for ski vacations in the winters. I bake cookies and we sing along to Neil Diamond and Barenaked Ladies like we’re a couple of soccer moms and dads. (I still need to learn all the words to Desiree because it’s getting embarrassing.)

Our least favorite road trip was the one where we towed all of his stuff from Newfoundland to Daytona Beach in four days. Because it’s practically impossible to cover that distance in four days comfortably, safely, and with your sanity intact. Roughly 4,000 km (that’s 2,485 mi for my American friends) and Google Maps clocks it at 50 hours. The engineer half of us (note: I am not the engineer) did not account for the weight of tow load. So our speed was reduced and we were driving for 16, 17 hours a day with no time for breaks. Just drive-throughs and roadside hotels, leg cramps and an overnight ferry crossing with no air conditioning. It very nearly ended our relationship, much like our first ski vacation where he thought he could teach me to downhill ski for the first time by simply letting me loose at the top of the slope.

So we were overdue for another fun road trip, finally, two years later. Our first destination in Florida was supposed to be Miami, but thesis life had other plans. Instead, our first road trip came highly recommended by his Aunt Michelle – St. Augustine, about an hour north of Daytona Beach.

We set off in my new Corolla. We were dieting, so this time there was no homemade cookies. We took the slightly longer, but much more scenic route, the A1A highway, which follows the coast from the unsubtle “World’s Famous Beach” sign, along the oceanfront and sandy beaches, lined with coastal mansions, palm trees and Trump supporter signs. Ignoring the latter, it’s a very beautiful drive.


St. Augustine is a lot like St. John’s, the small city where I’m from. St. Augustine is the oldest continuously occupied European settlement on the continental USofA, founded in 1565 by a Spanish admiral. St. John’s was officially established as a permanent community sometime after 1630, but because it existed on maps as early as 1519, it is the oldest city in North America.

St. Augustine was the capital of Spanish Florida for over 200 years, until Spain gave up Florida to the US in 1819. St. Augustine still looks like a small Spanish village on the Mediterranean, and its historical character makes it a major tourist attraction. That, and it’s the birthplace of Ray Charles. Enter: me.


The change in pace, in setting, in culture, in beauty from DB was instantly refreshing and I felt like I was transported to Europe. The first stop of the day was the Castillo de San Marcos, the oldest masonry fort in the continental US. The first coquina stones (rock made up almost entirely of seashells) were laid in 1672 and it was completed in 1695. This makes it about 100 years older than the original fortifications at Fort Amherst in Newfoundland.

coquina stone, made almost entirely of seashells

I admit I was too cheap to pay the admission to actually go in the Castillo (just as I was content to view Stonehenge through its looped wire fencing), but I enjoyed walking the perimeter of the impressive fort, with the gorgeous view of the Matanzas Bay, and witnessing an awesome awkward family photo.


siblings posing next to canons all in a row

This would make a great pregnancy announcement for their 8th baby

Then we walked the historical district, on the pedestrian-only roads of St. George’s and Avilés, packed with little local shops and galleries and cafés that spill out into the cobblestone streets, where you can touch the textiles, taste the tapas, and see original oil paintings. There’s endless handcrafted jewellery and gauzy asymmetrical dresses. The streets look cheerful and colorful, almost like an Epcot pavilion.


I’ve noticed something that I’ve come to admire about Americans and that’s their unrelenting enthusiasm to celebrate their own history. Signs everywhere for “the first school house”, the “first drug store,” all looking slightly inauthentic and cartoony. Here, they also have embraced the European history, too, with a one-tenth scale (and hilarious) replica of the Moorish Alhambra Palace in Granada.


We had lunch at a small Cuban restaurant, and headed off on a quick walking tour before the real point of our afternoon. We saw the tiled mosaic, the Government House, the Roman Catholic Cathedral of St. Augustine, the former Hotel Alcazar (now the Lightner Museum and City Hall), and Flagler College. There are trolleys and horse-drawn carriages to cart you around, but the whole town is very easily accessible by foot.


I really loved seeing the gift from St. Augustine’s sister city, Avilés, in Asturias, Spain. Displayed in Old Town, on Charlotte Street, it’s a beautiful ceramic tile mosaic depiction of the history linking to the two countries against the backdrop of their respective flags.

colorful ceramic mosaic tile in Old Town of American and Spanish flags

But for us, the highlights of the day were our FREE tours of the St. Augustine Distillery and the San Sebastien Winery, both of which also included FREE tastings! If you look on Trip Advisor for the top things to do here, the Distillery tour is #1. It’s locally owned in a restored ice plant from 1907, and produces handcrafted, award-winning rum, bourbon, whiskey, gin, and vodka. (All made from regionally grown, sustainably sourced ingredients, if you’re into that kinda great thing.) Our guide Amber was wicked and the tour was quite brief (mostly one room, in fact). But you don’t mind the brevity once you realize you’re being herded into a tasting room as your last stop and get to sample not one, not two, but FOUR craft liquor cocktails.

Now, I’m not a big drinker, except for gin, and there was gin, but I loved tasting their craft bourbon, rum and vodka. I had the best gin & tonic I’ve ever tasted there, and sure, the Rum Tiki was very popular. But the Florida Mule blew me away and I wanted to make off with a giant bottle of that gingery mule mix and take a bath in it.

A stone’s throw away was the San Sebastien Winery. We were there on a Sunday afternoon, which meant a self-guided tour (read: speed walking from tasting station to tasting station). This free tour came with not two, not six, but EIGHT free wine tastings, from dry whites to fruity reds and sweets rosés and then a port and sherry. Just call me Fraser Crane. The wines weren’t that good, but the cheese samples were delish and I had a brief nap in the video theatre where I remember hearing Florida is (surprisingly) the birthplace of American wine.


We strolled back to the old part of town, stopping for one last wine flight for my husband, before cruising back to Daytona, all in time for me to cook a two-veg-one-protein supper. The day was a win, and one of the best days in Florida we’ve had. I plan to go back once the school semester starts up so I can properly shop in the boutiques and maybe pick out something to hang on our walls. I also want to stay on the other side of the Bay and climb the famous lighthouse. This day trip will also be a highly rated “must-do” for any visitors that stay with me. Thank you, St. Augustine, for being the beautiful little European-esque oasis that you are. I’ll be seeing you.




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