St. Augustine Food and Wine Tour: Exploring History and Flavors

Strolling along quaint cobblestone streets, sipping divine wine, and indulging in decadent dishes in the heart of the oldest city in the United States.

Enter the Wine and Dine chauffeured tour in St. Augustine — the perfect medley of cultural immersion, gastronomic exploration, and historical enlightenment. Keep reading as I spill the sauvignon blanc on my day spent with five other winos and our fabulous guide, Dawn, while on this effervescent St Augustine Food and Wine Tour. Spoiler alert: this is no ordinary walking tour!

Chardon-hey! Meeting Our Guide and Group

15 minutes before our 1:30 pm tour, my ‘partner in wine’ and I stepped into the Old Solla-Caraba Cigar Factory Building, located at 88 Riberia Street. This beautiful golden brick building, built in 1909, once housed a booming Cuban cigar factory. It now houses several offices and meeting spaces, one being our tour operator, The Tasting Tours. As a bit of a history nerd, I was thrilled to experience firsthand the repurposing of a historical site.

Our culinary escort, Dawn, greeted us with a warm smile and a brief overview of what we could expect for our day. After we met our fellow tour mates, we headed back outside. Dawn then led us to an extended golf cart, invited us to climb aboard, and then set out for our hand selected savory sojourn.

Outdoor space with yellow stone walls and a cobblestone floor with black patio furniture and red umbrellas surrounded by plants

A Hidden Gem: The Old City House

With a cheery yellow exterior and a rich historical charm, The Old City House beckoned us with an open arm. Tucked away in a secret corner of downtown St. Augustine, not far from the picturesque historic hotels constructed by Henry Flagler, Dawn revealed that this quaint spot was once a stable house for these very hotels back in the late 1700s.

As we stepped onto the well-adorned veranda, Dawn shared that she loves this restaurant in part because it is the place she and her husband met on a blind date some 20 years ago. Today, The Old City House serves dual roles as both a charming bed and breakfast and a restaurant renowned for its international delights.

We were led to a quiet corner, shrouded by a canopy of tropical plants, and shown to our black cast iron tables, each adorned with chilled glasses of Sauvignon Blanc. Needless to say, I didn’t need to be asked twice to take a seat. Basking in the spring sunshine, I tried not to drool as I enjoyed two tender ravioli stuffed with a creamy seafood riccata blend and tossed in a rich vodka-style sauce. The wine, perfectly paired, further elevated the experience!

Pro Tip: When dining at this establishment, sans food tours, try the Beef Tenderloin or Swordfish. I have it on good authority that they are the best in town.

The initial stop on our journey delivered a high standard, intensifying my curiosity about what other surprises Dawn was yet to unveil for us.

Floor to ceiling shelves filled with wine with a table in the middle of the room also filled with wine

A Toast to History: Carrera Wine Cellar

Next stop, the infamous Carrera Wine Cellar! Regarded as a seamless harmony of wine and history, this place spoke in hushed whispers of the tales of the past. Crisp air filled with the subtle scent of oak barrels and aged wine beckoned, and our group was willing to follow.

Our host, Bob, warmly welcomed us and swiftly delved into the captivating history of Carrera Wine Cellar. He shared that this cozy, 200-year-old home once functioned as a stand for fruits and nuts, with an open porch that warmly invited patrons. The porch has since been transformed into an enclosed foyer adorned with wine-inspired gifts and a checkout counter.

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As Bob led us up the age-worn porch steps and deeper into the house, he delved into the specifics of Carrera’s vision, highlighting a few distinctive features. For instance, their ‘Reserve Room’, a treasure chest holding a selection of rare, and specialty wines.

Naturally, we wondered, “Which bottle boasts the highest price tag in the Reserve Room?” He didn’t keep us in suspense. At a cool $4000, it was a touch beyond my personal vino budget. Yet another intriguing aspect of this cellar was their ‘Enomatic’ wine dispenser. Wine on tap? That definitely had my undivided attention!

Next, we were warmly nudged by our host to “belly up to the bar.” Anticipation rose as we took in the sight of polished wine glasses and vibrant charcuterie platters, prepared and awaiting our arrival.

Charcuterie board on a table with a wine glass next to it

It wasn’t long before the delightful sound of wine being poured echoed through the room.

Our first pour: A crisp pinot grigio

Then came the second: An unoaked chardonnay

The third pour warmed us with a hint of spice: A malbec

And the fourth and final pour: A full-bodied merlot

As the afternoon unfolded, conversations ebbed and flowed. We delighted in a variety of textures and tastes – creamy parmesan cheese, briny macadamia nuts, fruity dried apricots, and the classic crunch of crackers.

Fun Fact: Carrerra Wine Cellar has been voted the “Best Wine Store” and “Best Wine Selection for a Restaurant/Bar” in St. Augustine!

Our insightful host shared with us a valuable trick for wine lovers. When it comes to the perfect temperature for your wine, the rule of thumb he provided was fairly simple.

If you’re about to indulge in a bold red, chill it briefly in your fridge for 20 minutes right before serving. On the other hand, if a crisp white is your pick, let it breathe by taking it out of the fridge and allowing it to sit on your counter for the same amount of time before you pour your glass.

Wide shot of a darkly decorated dining room with a floral ceiling and a bar in the background

Chez L’Amour: Gastronomic Delights to Remember

Our third destination brought us to Chez L’Amour. Dawn revealed to us that this restaurant had opened recently, November 2023, to be exact, after a long renovation post-pandemic. I was delighted to be one of the first to step through its doors and experience the whimsical beauty beyond.

Christened ‘House of Love,’ this venue spellbound me, not just with its flavors but visually, too. It was a space that can only be described as eclectic, whimsical, and sexy. Dramatic, dark floral wallpaper complemented perfectly by glass chandeliers hanging overhead. Lush green highlights meeting edgy neon signs. Gilded mirrors companioned with vibrant flora.

The bar? A nod to timeless elegance with its stately leather stools in a rich cognac shade neatly lined against a lustrously polished wooden bartop. It was unabashedly feminine, and I could’ve easily lost track of time exploring every nook and cranny.

Bar top with green glasses and a bar in the background filled with alcohol bottles

After a peek around the main floor, our group was led up a flight of stairs to a private dining room, where our senses were immediately entranced by the scent of freshly baked mochi rolls. Made from a unique mixture of potato and rice flour, they were divinely soft, subtly sweet, and lavishly buttery. Mingled with a smear of rich, earthy roasted red pepper butter, the rolls were a melt-in-my-mouth marvel.

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Our accompanying beverage at Chez L’Amour was a vivacious ‘Daytime Bourbon Punch,’ served cheerfully from a punch bowl at the center of our table. The sun-kissed medley of basil, lemon, apple, and blackberry evoked feelings of lounging leisurely on a sun-soaked porch with a warm summer breeze blowing gently.

Our culinary journey reached a flavorful peak with a succulent lamb meatball delicately perched upon a refreshingly herb-infused dressing and adorned with sprinkles of creamy goat cheese. As our palates relished the delightful masterpiece, Chef Ellie gave us insights into the restaurant’s diverse menu.

Half the offerings were vegetarian – a testament to their commitment to diverse culinary experiences. Her passion was palpable as she spoke about her aim to consistently deliver food that doesn’t just satiate but playfully excites and pleases.

Flirt with Flavors: An Excursion at Bourbon and Boards

The last leg of our gastronomical journey took us to a historic district hushed retreat – Bourbon and Boards. Flirting with the bold flavors of chocolate, we savored every morsel of our perfectly presented desserts. First up was the delectable almond truffle, completely gluten-free and vegan, boasting a creamy texture, offering a delightfully sweet interlude to our taste adventure. Paired with a generous pour of chardonnay, anticipation grew for the next course.

True to its surprise factor, the following plate was graced by ‘chocolate salami.’ Before you raise your eyebrows in suspicion, it bore a resemblance to chocolate bark, generously studded with crunchy nuts and garnished with whipped cream and a fresh strawberry.

The closing act of our dessert course was an elevated rendition of the classic Ho Ho Cake. Imagine plush chocolate cake layered with a delicate orange-flavored cream and topped by a thin spread of chocolate frosting. Of all the desserts, this final act stole the show; I can’t recommend it enough.

Tables and chairs in a dining room

St. Augustine’s Best Kept Secret: Wine and Dine Tours in St Augustine with a Personal Touch

As the sun began to lower in the sky, tinting the city with that golden hue only Florida can provide, I found myself on the brink of saying farewell. After several hours of indulging in award-winning flavors, drinking in rich history, and creating precious memories, my St. Augustine adventure was drawing to a close.

The experience of the Wine and Dine Chaufered tour was unmatched, and Dawn, who deservingly has been awarded “Tour Guide of the Year” many times, made it all the better.

If you find yourself in America’s Oldest City, take a walk on the wine side and sip your way through her ancient streets on this fantastic tour.

Have You Experienced St. Augustine’s Culinary Excellence?

Have you enjoyed a food and wine tour St Augustine? Share your favorite restaurant below!

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Written by Kelsi Johnson

Meet Kelsi, a Colorado-based writer and editor for Tripster. When she isn't behind the keyboard crafting engaging travel content, you'll find her hiking...

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