A Taste of History and Flavors: St. Augustine’s Wine, Cocktail and Food Experience
When you think of St. Augustine, you likely picture cobblestone streets, Spanish fortresses, and centuries-old buildings. But what about its culinary scene? For those wanting to combine history with a delicious twist, the St. Augustine Wine, Cocktail and Food Experience offers a perfect blend. For $154 per person, you’ll spend around three and a half hours strolling through some of the city’s most iconic spots, sampling local food and beverages alongside a knowledgeable guide. Led by Garry or Russ, you’ll get insider insights into the city’s stories while savoring top-quality bites and drinks.
What we love about this tour is its well-curated stops—each venue offers a genuine taste of local cuisine and drinks, and the guides are celebrated for their enthusiasm and depth of knowledge. Plus, the tour’s small group size, capped at eight travelers, means you get a more personalized experience. However, if you’re not keen on walking or have dietary restrictions beyond vegetarian options, you might want to plan accordingly. This tour suits those who enjoy authentic eats, historical context, and lively conversation, making it ideal for curious travelers eager to explore St. Augustine beyond the usual tourist paths.
Key Points

- Authentic Experiences: Sample food and drinks from some of the city’s best eateries.
- Historical Context: Guides share engaging stories about St. Augustine’s landmarks and past.
- All-Inclusive Sampling: No hidden costs—food and alcohol are included.
- Intimate Group: Max of 8 travelers for a relaxed, personal feel.
- Convenient Location: Tour starts near the historic city center and ends on vibrant Aviles Street.
- Duration & Timing: 3.5 hours starting at 2 pm, perfect for a relaxed afternoon.
Exploring the Streets and Sights of Historic St. Augustine

The tour kicks off at 57 Treasury Street, just a short walk from the city’s historic core. From there, your guide—either Garry or Russ—will lead you through a series of stops that are as much about learning as they are about tasting. Each part of the itinerary is designed to give you a layered experience of St. Augustine’s architecture, history, and local flavor.
If wine interests you, we've examined these other wine experiences in St Augustine
The Castillo de San Marcos: A Glimpse into the Past
Your journey begins with a visit to the Castillo de San Marcos, the oldest masonry fortification in the continental U.S., built in the 17th century by the Spanish. At 325 years old, this impressive structure is a powerful reminder of the city’s strategic importance. While the tour doesn’t include interior access, the views of the fortress from the outside are worth marveling at, and you’ll learn about its role in defending Spain’s claims in the New World.
The Huguenot Cemetery: A Quiet Reflection
Next, you’ll pass by the Huguenot Cemetery, established in the early 19th century. This Protestant burial ground was created due to the city’s religious diversity—an interesting contrast to the Spanish Catholic roots seen elsewhere. Since it’s only a five-minute stop, it’s more about the serenity and historical significance than extensive sightseeing. Many reviews highlight its importance as an often-overlooked part of the city’s story.
St. George Street: Heart of the Historic District
Winding your way through St. George Street, the tour enters the city’s vibrant pedestrian corridor. This street, framed by centuries-old buildings, is the backbone of downtown. You’ll pass charming shops, historic facades, and lively cafes. It’s an excellent spot to soak in the atmosphere, and many say it’s where the city’s authentic vibe begins to shine through.
The St. Photios Greek Orthodox National Shrine
Just off St. George Street, you’ll find the St. Photios Shrine, dedicated to the first Greek settlers arriving in 1768. This small but meaningful site offers a glimpse into the city’s diverse cultural tapestry. It’s a quick stop but adds a layer of global history to your walk.
Plaza de la Constitución and the Cathedral Basilica
At the heart of the city, the Plaza de la Constitución—the original town square—is a must-see. Surrounded by important landmarks like the Cathedral Basilica (constructed between 1793 and 1797), this historic park is the perfect spot to pause. The church, the oldest Christian congregation in the contiguous U.S., is a highlight. Many visitors note that the blend of Spanish, British, and American influences is visible throughout this area.
Government House and the Town Plaza
Your final stop takes you to the Government House, which has served various administrative roles since 1598. Sitting at the west end of the plaza, it offers great views of the harbor and is steeped in history. Here, the guide shares stories of the colonial governors and the evolving governance of Florida.
The Food, Drink, and Atmosphere
The real heart of this experience is, of course, the sampling of local cuisine and beverages. Every stop offers well-curated bites and drinks, including wines, cocktails, and regional dishes. Many travelers rave about the quality of the food—each bite is described as “top-notch”—and the wide variety of drinks available, from locally sourced wines to creatively crafted cocktails.
One review states, “The food was exceptional. Every bite was perfect,” and many mention that they bought bottles of wine at the wine bar, highlighting the value beyond just the tour experience. The fact that all samples are included—no hidden fees—adds to the sense of genuine value.
Guides Who Make the Difference
The guides are consistently praised for their knowledge, enthusiasm, and ability to blend humor with history. Reviewers mention Garry’s storytelling skills and Russ’s engaging commentary, which makes the walking tour both informative and entertaining. The small group size means you can ask questions freely and get personalized attention.
Authenticity and Hidden Gems
Many reviews mention discovering hidden spots and local favorites that they might not find on their own. This is particularly appealing to those who want a more intimate, insider’s view of the city.
Practical Details and Value
At $154, the tour offers themed stops, expert guidance, and a memorable experience that many feel outweighs the cost. It’s especially attractive for travelers who value quality over quantity—expecting delicious food, well-chosen drinks, and engaging storytelling.
The tour is scheduled to start at 2 pm, making it a great way to spend a leisurely afternoon. Since it lasts about three and a half hours, it’s not overwhelming but deep enough to feel satisfying.
Possible Drawbacks and Considerations

While most reviews highlight the positive aspects, some mention the walking component—it’s a moderate stroll with stops, so if mobility is an issue, plan accordingly. Also, since the tour is focused on food, drinks, and history, it might not be ideal if you’re seeking a purely culinary or historical experience without the walking element.
Plus, dietary restrictions beyond vegetarian options may not be accommodated, so if you have specific allergies or diets, it’s best to clarify in advance.
Who Should Book This Experience?

This tour is perfect for food lovers who want to enjoy a multi-sensory exploration of St. Augustine. It’s also ideal for history buffs who appreciate stories behind the sights and enjoy small group conversations. If you prefer guided walking tours with great food and drink, this experience checks all those boxes.
Travelers who like authentic local flavors, enjoy off-the-beaten-path discoveries, and want a personalized experience will find this tour well worth the price. It’s also a fantastic way to meet fellow travelers and get a comprehensive introduction to the city’s character.
FAQs

What is included in the tour?
All food and beverage samples are included, such as drinks, cocktails, and regional bites. Bottled water is also provided.
How long does the tour last?
Approximately 3 hours and 30 minutes, starting at 2 pm.
Where does the tour start and end?
It begins at 57 Treasury Street and ends on Aviles Street near the Plaza de la Constitución.
Is this tour suitable for vegetarians?
Yes, vegetarian options are available. However, other dietary restrictions like vegan or gluten-free are not accommodated.
What is the group size?
The tour is limited to a maximum of 8 travelers, ensuring a relaxed and intimate atmosphere.
Are there any additional fees?
No, all food and drinks are included with your ticket—there are no hidden costs.
Can I cancel the tour?
Yes, cancellation is free up to 24 hours before the start time for a full refund.
Is the tour accessible by public transportation?
Yes, it’s near public transit options, making it easy to reach the starting point.
What should I wear?
Comfortable walking shoes are recommended as you’ll be strolling through historic streets. Dress for the weather, and bring a small umbrella if rain is forecasted.
To sum it up, the St. Augustine Wine, Cocktail and Food Experience offers a thoughtful, delicious way to discover the city’s sights, history, and flavors all in one go. Perfect for those who love engaging guides, quality food, and a relaxed pace, it provides a memorable taste of what makes St. Augustine so special. Whether you’re a history enthusiast, a foodie, or simply looking for a fun way to spend an afternoon, this tour delivers a compelling combination of education and enjoyment.
More Food & Drink Experiences in St Augustine
More Tour Reviews in St Augustine
- Torrid Tales True Crime Walking Tour of St Augustine
- Freeedom Photo Adventure Experience In St. Augustine
- Adventure Boat Tours – One Hour Dolphin/Eco/History/Sightseeing Boat Tour
- St Augustine Self Guided Ghost Hunt Adventure
- Dolphin and Wildlife History Tour
- Walking Tour in North City Cemeteries of St. Augustine
More St Augustine experiences we've covered
- Torrid Tales True Crime Walking Tour of St Augustine
- Freeedom Photo Adventure Experience In St. Augustine
- Adventure Boat Tours – One Hour Dolphin/Eco/History/Sightseeing Boat Tour
- St Augustine Self Guided Ghost Hunt Adventure
- Dolphin and Wildlife History Tour
- Walking Tour in North City Cemeteries of St. Augustine
- St Augustine Inshore Fishing Charter
- Bones Under Us, Ghost Tour with Archeology
- Spirits with the Spirits haunted pub crawl – drinks included
- Adventure Boat Tours – Nights of Lights by Water in St. Augustine FL
- St Augustine History and Cheesecake Golf Cart Tour
- Americas Oldest City: A Self-Guided Walking Tour of St Augustine
