I instantly fell in love with St. Augustine the moment I walked into the historic district. The quaint storefronts and colorful wooden balconies made it look like a pirate theme park, but there’s so much more to the oldest city in the USA than tourism and homemade fudge. I was only in town for two nights, so a sightseeing food tour was the perfect way to explore and gain local knowledge about the best eateries in the area.
| The Gifted Cork
I met my tour guide, Seth, at the Gifted Cork on Hypolita Street, a small but well stocked wine bar where we’d be having our first tasting. I happened to be the only person booked onto this tour, so I was expecting the VIP treatment! Our server, Sam, offered us a choice of four wines from their vast selection, but I don’t know enough about wine to confident order so I let her decide. She went for two reds and two whites, paired with a sweet and soft champagne cheese with apricot jelly, a chive and onion British cheddar, and a porter beer cheese. We also got to taste a super sweet blue wine, which was as tasty as it was colorful!
| The Liberal Arts Flagler College
Out into the rain, we passed the liberal arts Flagler College which was once the Ponce de León Hotel, an impressive structure built in 1888 by John Carrere and Thomas Hastings. Across the street was the Case Monica Hotel, also built in 1888 and opened by Franklin Smith, and our second stop on the tour. We were shown through the lavish bar area into a private ‘Wine Room’, which was decorated with large oil paintings and featured several metal cases of extremely old and expensive wine (one of which was rented by a regular guest, and even the manager didn’t know how much for).
The hotel manager, Alex, greeted us and explained what we’d be eating and drinking; their signature crab cake, sweet and salty patatas bravas, and fried octopus paired with a Cabernet Blend chosen by Richard Kessler, the current hotel owner. Alex also told us the fascinating story of how he came to be in America after travelling from his home town of Italy, following his brother across the world the land in Iowa (which he disliked), but eventually discovering St. Augustine where he decided to settle.
| Corazon Cinema
Back on the brick-lined streets, we walked through Café Alcazar to get to our next stop, a very sophisticated space which was once the largest indoor swimming pool and is now the Lightner Museum. This took us straight through to the Corazon Cinema, a fantastic independent theatre showing indie and foreign movies and serving great southern food, plus a fantastic wine selection and regular trivia nights! Our host served us a selection of sandwiches; turkey, ham, egg mayo, and chicken salad, plus coleslaw and potato salad, whilst we watched a short documentary clip about the city of St. Augustine - definitely not something I’ve experienced on a food tour before!
| Ancient Olive
A few doors down was our next stop, the wonderful Ancient Olive, an oil and vinegar store that has more flavors than you can possibly imagine. We were welcome to walk around and taste as many as we wanted, so I went for a passionfruit balsamic vinegar, maple syrup vinegar, mint and citrus olive oil, and a very delicious stout jelly that would go exceptionally well with the cheese we had at the Gifted Cork. I may have to come back and do some shopping!
| Barley Republic
Next up was Barley Republic, a traditional Irish bar where we could choose our drink (I went for their pinot grigio thinking it best I stick to wine), and try their classic fish and chips with a decidedly American take on tartare sauce. Can’t say there was much history to be discussed in an Irish bar, I think it was just an excuse to try some really great food! It lead us nicely onto our final stop on the tour though, the iconic Peace Pie. Now I’ve never been one for biting ice cream, even the thought makes my teeth hurt and the threat of brain freeze starts to set in, but when ice cream is sandwiched between cookies with a layer of pie, I had to give it a go.
| Unique Twist On A Pecan Pie
First up was their original pecan pie flavor, and although my teeth were protesting, it was some of the best ice cream I’ve ever had. Our server told us the history of how the peace pie came about; how creator Jerry Klause intended to make a pecan pie but forgot the pie crust, so instead spread the filling between two layers of tray-bake cookie, and added some ice cream for good measure. His family enjoyed it so much, a business venture was born! We followed the pecan pie with their best-seller; salted caramel brownie (there’s a reason it’s the best-seller, I’m telling ya). Finally, we finished with classic strawberry shortcake, which Seth claimed was his favorite, but I think the pecan pie takes it for me.
That was the end of our gourmet escapade, but I certainly wasn’t going home hungry for more food or knowledge. Seth was a fantastic guide and I’m hugely thankful he didn’t cancel given the particularly small group size (i.e. just me), as it was more like hanging out with a friend (who knew a great deal about the area) than a structured tour. I’d highly recommend the food tour as a must-do for anyone visiting St. Augustine, and a great gift idea for anyone into their American history!
| Thanks For Reading