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

If you’re considering a way to truly soak up the charm of Florida’s oldest city, this St. Augustine walking tour might just be what you’re looking for. It’s a laid-back, 3.5-hour stroll that offers a delightful mix of history, local flavors, and scenic views, all wrapped into one memorable experience. Whether you’re a foodie, a history buff, or just someone who enjoys a good drink with a side of culture, this tour promises a relaxed yet engaging day.

What caught our eye about this tour are two things: the focus on local flavors paired with historical insights, and the small group setting that makes everything feel intimate and personalized. On the flip side, a potential consideration is that it’s primarily an afternoon activity, so if you’re a morning person, you might want to plan around that. It’s a tour that suits travelers eager to combine leisurely walking with tasty tastings and fascinating stories — think of it as a culinary and historical sampler.

Key Points

• Flexible & intimate: Small group size ensures personalized attention.
• Taste & learn: Combines food, drinks, and history seamlessly.
• Scenic & historic routes: Walks along Aviles Street, the oldest in the U.S.
• Well-curated stops: Three venues with wine, cocktails, and food tastings.
• Knowledgeable guides: Well-reviewed guides who enhance the experience.
• Ideal for leisurely afternoons: Warm weather, scenic streets, and cultural insights.

You can check availability for your dates here:

A Deep Dive Into the Experience

This walking tour, priced at $159 per person, is designed to give you a taste of St. Augustine’s historic streets and culinary scene in a relaxed four-hour window. The tour kicks off at Casa de Vino 57 — a cozy spot that immediately sets a welcoming tone. From there, your guide will lead you through the city’s charming cobblestone streets, with Aviles Street being a highlight. As the oldest street in the nation, walking here feels like stepping back in time, with charming shops, galleries, and historic buildings lining the way.

What really makes this tour stand out, especially for those who love a good story, is the blend of history and flavor. Along the route, you’ll see landmarks like the Old City Gates and the Castillo de San Marcos, both of which add richness to the experience. The tour doesn’t just focus on the past; it also provides a lively taste of current local flavors. You’ll enjoy a complementary glass of wine, paired with two handcrafted cocktails, and a variety of food tastings that showcase the city’s culinary offerings.

The Stops and Their Charm

Each of the three venues selected for this tour offers a unique taste of St. Augustine. The first stop is typically a place where you’ll enjoy a wine tasting and perhaps some charcuterie, giving you a chance to sample Florida’s local wines and mingle with fellow travelers. The second venue emphasizes cocktails — colorful, thoughtfully crafted drinks that showcase local ingredients and bartenders’ creativity. The final stop usually includes a delicious food tasting, rounding out the tasting experience with flavors that reflect the city’s diverse history.

One of the most praised aspects, according to reviews, is the guides’ knowledge and friendliness. Many mention how guides like Alex, Russ, and Garry go above and beyond, sharing interesting stories and making personalized suggestions. As one reviewer put it, “Alex was an excellent guide and molded the tour to our interests,” reflecting the flexible, friendly nature of this experience.

The Food and Drink

This isn’t just a sightseeing tour; it’s a culinary journey. The food tastings are generally well-received, offering a variety of bites that pair nicely with the drinks. The wine tasting is described as a good introduction to local wines, and the cocktails are crafted with care, adding color and flavor to the afternoon.

For travelers who enjoy sampling local flavors and learning about the city’s culinary scene, this tour hits the mark. Guests often leave with not only full bellies and happy drinks but also helpful tips from guides about what to explore next in St. Augustine.

Accessibility and Practicalities

The tour is suitable for most travelers who can walk at a leisurely pace. It lasts 3.5 hours and involves visiting three venues, with plenty of time to enjoy each stop. It’s wheelchair accessible, which is a plus, and the small group makes it easier to stay together and ask questions. Be sure to wear comfortable shoes and bring your ID or passport, especially since alcohol is involved.

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Cons and Considerations

While this tour is highly praised, it’s not for those under 21, and dietary restrictions beyond vegetarian options aren’t accommodated. If you’re sensitive to walking or prefer a more structured, less flexible schedule, this might not be your best fit. Also, since tours run rain or shine, be prepared for the weather — an umbrella or hat might come in handy.

Who Will Love This Tour?

If you’re a traveler who enjoys combining culture, history, and food in a relaxed setting, you’ll find this tour well worth your time. It’s perfect for first-timers wanting a comprehensive introduction to St. Augustine’s streets and flavors, or for those who’ve visited before but want a new way to experience the city. It’s especially suited for adults who appreciate good wine and cocktails, and who like the idea of strolling through scenic streets while learning local stories.

Travelers who enjoy small, intimate groups will appreciate the personalized touch, and those looking for a fun, social activity with friends or a partner will find it a hit. If you’re visiting with a group that has varied interests — some into history, others into food and drinks — this tour does a nice job of balancing both.

Final Thoughts

All in all, this St. Augustine walking tour offers a well-rounded experience with a good mix of history, food, and drinks. The small-group setting and knowledgeable guides really elevate the experience, making it feel like a friendly exploration rather than a touristy shuffle. The combination of scenic streets, historical sites, wine, cocktails, and tasty bites makes it a compelling choice for those wanting to savor the city in a relaxed, engaging way.

If you’re after an activity that’s more than just sightseeing — something that feeds both your curiosity and your appetite — then this tour is worth considering. It’s a nice way to start your visit or to enjoy a laid-back afternoon during a longer stay. Just be sure to wear comfortable shoes, come hungry, and be ready for a memorable taste of St. Augustine.

FAQs

Is this tour suitable for people with mobility issues?
Yes, it’s wheelchair accessible, and the pace is slow and comfortable, making it doable for most visitors with mobility considerations.

How many people are in each group?
The tour is limited to 8 participants, which keeps the experience intimate and allows for better interaction with the guide.

What should I bring?
Bring your passport or ID card and wear comfortable shoes since it involves walking through historic streets.

Is the tour suitable for vegetarians?
A vegetarian option is available, but other dietary restrictions aren’t accommodated.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, offering good flexibility.

What time does the tour usually run?
It is usually available in the afternoon, making it a perfect midday or early evening activity.

Are kids allowed?
This tour is only for those 21 and over due to alcohol consumption, so it’s not suitable for children or teenagers.

If you’re looking to blend history, flavor, and fun into one leisurely outing, this tour of St. Augustine might just be the highlight of your trip. Think of it as a friendly exploration — full of stories, smiles, and good eats.

You can check availability for your dates here: