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

Discover the Charm of St. Augustine’s Oldest Streets and Historic Sites

This 3.5-hour guided walking tour in St. Augustine, Florida, combines local history, flavorful food, and refreshing drinks for an engaging experience. Priced at $159 per person, it offers a well-rounded introduction to the city’s rich past and vibrant culinary scene. The tour is perfect for those who enjoy exploring on foot at a relaxed pace, with plenty of opportunities to sample wine, cocktails, and local bites along the way.

What sets this tour apart is its focus on both the historic architecture and the lively food and drink culture. From cobblestone streets lined with shops and galleries to iconic sites like Old City Gates and Castillo de San Marcos, every stop offers a chance to learn about the city’s past while enjoying the present-day flavors. The tour is suitable for most visitors, but note that it is not designed for those under 21 years old and requires comfortable shoes for walking.

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Key Points

• Duration: 3.5 hours of engaging walking with frequent stops
• Price: $159 per person, includes wine, cocktails, and food tastings
• Location: Starts at Casa de Vino 57 in historic downtown
• Highlights: Explore Aviles Street and other landmarks, enjoy a complementary wine tasting, and sip on two handcrafted cocktails
• Small Group: Limited to 8 participants, ensuring personalized attention
• Accessibility: Suitable for wheelchairs, with a slow and comfortable pace

Starting Point in the Heart of Historic St. Augustine

The tour begins at Casa de Vino 57, located in the lively courtyard where you’ll meet your English-speaking guide. This accessible meeting spot sets the tone for a relaxed, friendly experience. From here, the group embarks on a leisurely walk through the narrow, cobblestone streets that define St. Augustine’s charm.

The tour’s pacing allows ample time to absorb the sights without feeling rushed. As it takes place rain or shine, participants should come prepared with comfortable shoes and a passport or ID for identification purposes. The small group size guarantees a intimate atmosphere, making it easier to engage with your guide and ask questions.

Exploring Aviles Street, the Oldest Street in the U.S.

A key highlight is walking along Aviles Street, the oldest thoroughfare in the United States. This historic street is lined with colorful shops, galleries, and restaurants, each telling a piece of the city’s story. The guide shares insights into the architecture and history behind these storied buildings, bringing the past to life as you stroll.

This section offers excellent photo opportunities and an authentic feel of old Florida. The street’s lively vibe is complemented by views of colonial architecture and the distant silhouette of a 17th-century Spanish stone fortress — a perfect setting for absorbing the city’s layered history.

Wine Tasting at a Historic Venue

One of the tour’s most appreciated features is the complementary wine tasting. The guide leads participants to at least one carefully selected venue where a glass of wine is included in the experience. The location enhances the tasting with its historic charm, adding depth to the sensory experience.

The wine selection offers a taste of Florida’s local flavors, giving guests a chance to appreciate regional wines in a relaxed setting. This stop is also a chance to enjoy light food accompaniments, such as charcuterie boards, which balance the drinks beautifully.

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Sampling Two Handcrafted Cocktails at Local Venues

Along the route, you’ll indulge in two handcrafted cocktails, each crafted to showcase local ingredients or classic styles with a fresh twist. The guide recommends and introduces these drinks, which are served at carefully chosen venues that reflect the city’s lively ambiance.

These cocktails serve as a refreshing highlight, offering a taste of Florida’s vibrant bar scene. Between sips, the guide shares stories behind the drinks, adding a personal touch to the experience. This part of the tour appeals especially to those who enjoy discovering new cocktail styles.

Visiting Key Landmarks: Castillo de San Marcos and Plaza de la Constitución

Between food and drinks, the tour includes viewings of notable sites such as Castillo de San Marcos, a 17th-century Spanish fortress, and Plaza de la Constitución, the historic heart of downtown. From the fortress, you can enjoy views of its sturdy stone walls and learn about its strategic importance.

The Old City Gates also feature in the route, marking the entrance to the historic district. These landmarks are explained in detail by your knowledgeable guide, connecting their significance to the broader story of St. Augustine’s colonial past.

Unique Features of the Guided Experience

This tour is led by expert guides who craft a personalized experience based on the small group setting. Past reviews highlight guides like Alex and Garry for their friendly demeanor, insightful stories, and flexibility in tailoring the tour to participant interests.

The pace remains slow and comfortable, making it accessible for most visitors. The tour includes food tastings, with a focus on local flavors, and a variety of drinks that complement the scenic route. This careful curation helps create a well-balanced experience for lovers of history, cuisine, and drinks alike.

Practical Details and Considerations

Participants should bring comfortable shoes and a passport or ID card. The tour takes place rain or shine, so dressing appropriately for the weather is advised. Pets are not allowed, though assistance dogs are permitted.

While the tour offers vegetarian food options, it cannot accommodate other dietary restrictions. It is designed primarily for adults over 21, who can enjoy the full range of tastings and cocktails. The small group limit of 8 enhances interaction with the guide and ensures a relaxed atmosphere.

Why This Tour Is a Great Choice for Visitors

This walking tour combines historic exploration with culinary delights, making it an ideal choice for those who want a taste of St. Augustine’s past and present in a single experience. The small group size and expert guides ensure personalized attention and a friendly environment.

Price-wise, it offers good value considering the wine, cocktails, and food tastings included. It’s especially recommended for visitors who appreciate knowledgeable storytelling, scenic streets, and local flavors. However, those seeking a more physically active or longer tour might find this experience perfectly suited for an afternoon of relaxed enjoyment.

Frequently Asked Questions

What is the duration of the tour?
The tour lasts for 3.5 hours, providing plenty of time to explore, taste, and learn without feeling rushed.

Where does the tour start?
The tour begins at Casa de Vino 57, in the courtyard area, where you meet your English-speaking guide.

What is included in the price?
The price covers a guided walking experience, one glass of wine, two cocktails, and food tastings at select venues.

Is the tour accessible for wheelchairs?
Yes, the tour is wheelchair accessible and designed for a slow, comfortable pace.

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

Does this tour work for vegetarians?
Yes, a vegetarian option is available, though other dietary restrictions cannot be accommodated.

Is the tour suitable for children under 21?
No, the experience is not suitable for those under 21 because of the alcohol tastings.

What should I bring?
Participants should bring comfortable shoes and a passport or ID card for identification.

Will the tour operate in bad weather?
Yes, the tour takes place rain or shine, so dress accordingly.

How many people are in each group?
The group is limited to 8 participants, ensuring a personalized experience with your guide.

This St. Augustine walking tour with wine, cocktails, and food offers a delightful blend of history, scenic streets, and flavorful drinks. It’s a fantastic way to experience the city’s colonial charm while enjoying regional wines and handcrafted cocktails. Perfect for adults seeking a relaxed, informative, and tasty afternoon in one of America’s oldest towns.

You can check availability for your dates here: More Great Tours Nearby