St. Augustine: Walking Tour with Wine, Cocktails, and Food

St. Augustine: Walking Tour with Wine, Cocktails, and Food — A Deep Dive

If you’re visiting Florida’s oldest city, St. Augustine, and longing to combine history with culinary delights, this guided walking tour offers an engaging way to spend an afternoon. For $159 per person, you’ll spend about 3.5 hours wandering the charming streets, sampling local wines and handcrafted cocktails, and soaking up the city’s storied past. Led by friendly, knowledgeable guides, this experience promises a well-balanced mix of cultural history and gastronomic pleasure.

What truly stands out are the delicious food tastings at curated venues and the complementary wine and cocktails that add a celebratory touch without breaking the bank. Plus, the walk itself through cobblestone streets lined with shops, galleries, and colonial architecture is a treat for the senses. The tour’s emphasis on authentic local flavors and historic sites makes it perfect for travelers wanting a relaxed yet enriching experience.

One thing to keep in mind is that since this is a walking tour, you’ll want to wear comfortable shoes. Also, while vegetarian options are available, other dietary restrictions aren’t accommodated, so it’s worth considering if you have specific needs. This tour really suits those who enjoy a leisurely pace, love history, and want to taste their way through St. Augustine with a small, friendly group.

You can check availability for your dates here:

Key Points

Authentic Experience: Combines historic sights with food and drink tastings for a well-rounded visit.
Expert Guides: Highly praised guides like Alex and Russ enhance the experience with engaging stories and local insights.
Taste of Local Flavors: Includes wine, two cocktails, and multiple food stops, making it a culinary highlight.
Small Group Setting: Limited to 8 participants for personalized attention.
Flexible Booking: Cancel up to 24 hours before for a full refund, with options to reserve now and pay later.
Accessible: Wheelchair-friendly, making it available to a wider range of travelers.

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Discovering the Historic Streets and Architectural Gems

Once you meet your guide in the courtyard of Casa de Vino 57, you’re set for an afternoon that blends history with culinary exploration. The walking pace is relaxed and comfortable, perfect for absorbing the sights and sounds of St. Augustine’s charming streets. Your guide will lead you through the narrow, cobblestone streets of Aviles Street, the oldest in the United States, lined with colorful shops, galleries, and cafes. Here, you’ll get a real sense of the city’s colonial charm and European influence.

One of the first stops is a venue offering a complimentary wine tasting. It’s a great way to start the experience, with local wines that showcase Florida’s historic coast. From there, the tour visits two additional venues for handcrafted cocktails that are both visually striking and flavorful. Many reviewers raved about the variety and quality of the drinks—some describing them as colorful, others as perfectly balanced.

Between sips and bites, you’ll view landmarks like Castillo de San Marcos, the oldest stone fortress in the continental U.S., and the Old City Gates, which have watched over the city since the 17th century. The Plaza de la Constitución provides a lively backdrop, where history and modern life intersect. Your guide will share stories about these sites, making the sights come alive with intriguing details.

The Food and Drink Stops: A Culinary Tour of St. Augustine

A major highlight of this tour is the variety of tastings. At three different venues, you’ll enjoy charcuterie boards, regional bites, and colorful cocktails. Many guests pointed out how these stops offered more than just drinks; they revealed local culinary traditions and flavor profiles specific to Florida’s historic coast.

One reviewer mentioned, “The tour was fabulous! We all enjoyed the variety of food and cocktails,” highlighting how the stops cater to a range of tastes. The food is thoughtfully curated to enhance the experience, making each stop feel like part of a culinary journey through the city. The complementary wine sets a relaxed tone early on, while the handcrafted cocktails add a playful and refreshing element later.

This tour is especially suitable for those who appreciate quality drinks and tasty bites—whether you’re a wine connoisseur or just enjoy discovering new flavors. It’s also a great way to sample local specialties without committing to multiple restaurants.

The Experience and the Guides

From the reviews, it’s clear that guides like Alex and Russ are a big part of what makes this experience special. Guests consistently praise their enthusiasm, storytelling skills, and willingness to personalize the tour based on group interests. Many mention how these guides enhanced their understanding of St. Augustine’s history without feeling overbearing or overly academic.

One guest said, “Russ was an amazing guide and our small group had a blast,” emphasizing the small group setting that fosters a more intimate experience. This personal touch means you can ask questions and get tailored recommendations for the rest of your day in the city.

The tour’s small size (limited to 8 participants) ensures that everyone gets attention, making it easier to connect and enjoy the shared experience. It also adds to the relaxed, friendly atmosphere many guests appreciated.

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Practicalities and What to Expect

The tour begins in the courtyard of Casa de Vino 57, which is a convenient and scenic meeting point. You should wear comfortable shoes—the cobblestone streets and walking pace make this a must—and bring a passport or ID, especially if you plan to enjoy the wine tastings responsibly.

Since the tour occurs rain or shine, be prepared with a light rain jacket if the weather forecast isn’t clear. The entire experience lasts about 3.5 hours, generally scheduled in the afternoon, making it a perfect way to wind down or start your evening explorations.

The tour includes one glass of wine, two cocktails, and food tastings at three venues. While vegetarian options are available, other dietary restrictions cannot be accommodated, so confirm if you have specific needs.

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Who Should Consider This Tour?

This experience appeals most to history lovers who enjoy a relaxed stroll through charming streets, as well as foodies and wine enthusiasts eager to sample local flavors. Travel groups, couples, or solo travelers wanting a small, intimate group will find this a perfect fit. It’s especially ideal for visitors who want to combine sightseeing with culinary exploration, rather than a typical historical tour.

It’s also a good choice for first-time visitors looking for a comprehensive introduction to St. Augustine, with plenty of tips from guides on what to see and do afterward.

The Sum Up

This St. Augustine walking tour offers a delightful combination of history, food, and drink in the city’s most picturesque streets. The small-group setting, knowledgeable guides, and carefully curated tastings make it a standout choice for those wanting an authentic, relaxed, and informative experience.

Whether you’re a history buff, a foodie, or simply someone who enjoys sipping and strolling in a charming setting, this tour provides real value. It’s perfect for travelers who appreciate quality guides and thoughtfully selected venues. Most importantly, it leaves you with a deeper appreciation of St. Augustine’s historic charm and local flavors.

FAQ

Is this tour suitable for people with dietary restrictions?
Vegetarian options are available, but other dietary restrictions cannot be accommodated. It’s best to inform the guide beforehand if you have specific needs.

How long is the tour?
The entire experience lasts approximately 3.5 hours, including walking, tastings, and sightseeing.

What should I wear?
Comfortable shoes are recommended, as you’ll be walking on cobblestone streets. Dress for the weather—rain or shine.

Where do we meet?
The meeting point is in the courtyard of Casa de Vino 57, a convenient location in downtown St. Augustine.

Is the tour wheelchair accessible?
Yes, the tour is wheelchair accessible, making it suitable for a wider range of guests.

Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

Are children allowed on this tour?
This tour is not suitable for people under 21 years old.

Do I need to pay upfront?
You can reserve now and pay later, offering flexibility if your plans change.

What’s included in the price?
The fee covers the guided walk, one glass of wine, two cocktails, and food tastings at three venues.

How many people are in each group?
The tour is limited to 8 participants for a more intimate experience.

Whether you’re a first-time visitor or a seasoned traveler, this tour promises a memorable afternoon filled with delicious tastes, captivating sights, and local stories. It’s a wonderful way to experience the heart of St. Augustine beyond the typical sightseeing routes.