Enjoy the historic charm of St. Augustine on an engaging walking tour. Explore the oldest street in the United States, Aviles Street, and savor the region’s coastal flavors through a curated selection of food tastings. As you stroll through the charming cobblestone streets, admire the stunning Spanish architecture, including the iconic Castillo de San Marcos. Complement your journey with a wine tasting and handcrafted cocktails, offering an unforgettable glimpse into the rich heritage and vibrant culture of this remarkable city. But the true delight lies in the unexpected discoveries that await around every corner.

Key Points

  • A 3.5-hour walking tour of St. Augustine’s historic Aviles Street, featuring food tastings, wine tasting, and two handcrafted cocktails.
  • Small group size of up to 8 participants for a personalized and intimate experience.
  • Accessible route designed for visitors of varying abilities, including wheelchair users.
  • Opportunity to explore the charming shops, galleries, and eateries along the oldest street in the United States.
  • Chance to indulge in the region’s rich culinary heritage and sample locally-sourced seafood and produce.

Duration and Group Size

St. Augustine: Walking Tour With Wine, Cocktails, and Food - Duration and Group Size

The tour lasts for 3.5 hours and is limited to a maximum of 8 participants, ensuring an intimate and personalized experience.

This allows the guide to provide more attention to each guest, creating a relaxed and engaging atmosphere. The small group size also makes it easier to navigate the historic streets and allows for more interaction with the local sights, sounds, and flavors.

Whether you’re exploring the nation’s oldest street or savoring handcrafted cocktails, you’ll have the opportunity to learn about the rich history and vibrant culture of St. Augustine at a comfortable pace. This thoughtful tour design ensures an unforgettable journey through this charming coastal city.

Accessibility and Mobility

St. Augustine: Walking Tour With Wine, Cocktails, and Food - Accessibility and Mobility

This tour is wheelchair accessible, allowing guests with mobility needs to fully participate in the experience.

The guided walk through St. Augustine’s historic streets and highlights caters to visitors of varying abilities, ensuring an inclusive and enjoyable tour for all.

The route is designed with accessibility in mind, navigating the cobblestone paths and uneven terrain with ease.

Guests using wheelchairs or other assistive devices can seamlessly take in the sights, sounds, and flavors of this charming coastal town.

The tour operator is committed to making the experience accessible and accommodating to all participants, regardless of their mobility level.

Aviles Street: Oldest in the Nation

St. Augustine: Walking Tour With Wine, Cocktails, and Food - Aviles Street: Oldest in the Nation

Anchoring the historic walking tour, Aviles Street stands as the nation’s oldest, tracing its roots back to the city’s founding in 1565. Lined with charming shops, galleries, and eateries, this cobblestone path offers a glimpse into St. Augustine’s storied past. Visitors can stroll along the quaint street, admiring the colonial architecture and soaking in the ambiance of this timeless location.

Feature Description
History Established in 1565, Aviles Street is the oldest street in the United States.
Ambiance The cobblestone path and colonial buildings create a unique, historic atmosphere.
Attractions The street is home to a variety of shops, galleries, and dining options for visitors to explore.

Taste the Historic Coastal Flavors

As visitors explore St. Augustine’s historic streets, they’ll have the opportunity to savor the vibrant flavors of Florida’s coastal region.

The tour includes food tastings that showcase the area’s culinary heritage, allowing participants to indulge in the unique tastes that have defined this seaside destination for centuries.

From fresh seafood to locally-sourced produce, the tour guides guests through a flavorful journey that celebrates the region’s rich gastronomic traditions.

Whether it’s a sampling of freshly-caught shrimp or a taste of the area’s signature citrus fruits, the food tastings provide an intimate connection to the land and waters that have nourished St. Augustine’s people for generations.

Stroll Through Cobblestone Streets

Visitors stroll along the charming cobblestone streets of St. Augustine, marveling at the historic buildings, quaint shops, and art galleries that line the walkways.

As they explore the area, they’ll discover:

  • Unique boutiques and specialty shops selling everything from local artisan goods to handcrafted souvenirs
  • Galleries showcasing the work of talented painters, sculptors, and photographers inspired by the city’s rich history and picturesque scenery
  • Cozy cafes and restaurants serving up delectable local cuisine and refreshing beverages
  • Occasional street performers adding to the lively ambiance of the vibrant downtown district

This charming stroll through St. Augustine’s cobblestone streets offers a delightful glimpse into the city’s captivating past and present.

Wine Tasting and Cocktails

St. Augustine: Walking Tour With Wine, Cocktails, and Food - Wine Tasting and Cocktails

Along the tour, participants savor a complimentary wine tasting and two handcrafted cocktails, allowing them to sample the local flavors of Florida’s historic coast.

The wine tasting offers a chance to explore the region’s signature varietals, while the cocktails showcase the creativity of local mixologists. These beverages perfectly complement the food tastings, providing a well-rounded sensory experience.

The wine and cocktails are carefully selected to highlight the unique character of the destination, introducing guests to the vibrant culinary scene. This aspect of the tour ensures that visitors don’t just see the sights, but truly enjoy the local culture and its delectable offerings.

Views of Spanish Fortress and Architecture

Strolling along the cobblestone streets, tour participants marvel at the captivating views of the 17th-century Spanish stone fortress and the well-preserved colonial architecture that line the historic district.

The iconic Castillo de San Marcos, a National Monument, stands tall as a testament to Spain’s colonial presence in the region.

Participants are struck by the remarkable detail and craftsmanship of the stone structures, which include:

  • Ornate wrought-iron balconies
  • Colorful stucco facades
  • Towering bell towers
  • Intricate archways and doorways

This immersive experience provides a unique opportunity to step back in time and appreciate the rich history and architecture that define St. Augustine’s charming character.

Meeting Point and Important Information

The tour begins in the courtyard of Casa de Vino 57, where you will meet their knowledgeable guide. Regardless of the weather, the tours proceed as scheduled, so visitors should dress accordingly for the outdoor exploration. While the pace is slow and comfortable, those with dietary restrictions beyond vegetarian options may find limited options available during the food tastings.

Tour Details
Duration 3.5 hours
Group size Limited to 8 participants
Accessibility Wheelchair accessible

Important Information:

  • Tours take place rain or shine
  • Slow and comfortable pace
  • Vegetarian option available, but other dietary restrictions cannot be accommodated

Frequently Asked Questions

Can I Bring My Pet on the Tour?

Unfortunately, pets are not allowed on the tour. The tour is designed for a small group, and the venues visited may have restrictions on bringing animals. For the safety and enjoyment of all participants, pets cannot be accommodated.

Do I Need to Bring Any Special Equipment?

No special equipment is needed for this walking tour. Participants should wear comfortable walking shoes and bring any necessary medications or assistive devices. The tour is wheelchair accessible, so mobility aids can be used during the tour.

Is the Tour Available in Languages Other Than English?

The tour is available in English only. The operator does not offer the tour in other languages at this time. Participants should be comfortable communicating in English during the 3.5-hour walking tour.

Can I Take Photos During the Tour?

Yes, participants are welcome to take photos during the tour. The tour encourages guests to capture the historic sights and local flavors of the experience. However, photography should not disrupt or interfere with the guide’s commentary.

What Is the Cancellation and Refund Policy?

The cancellation and refund policy allows participants to cancel up to 48 hours before the tour for a full refund. Within 48 hours, no refunds are available, but the tour may be rescheduled subject to availability.


This walking tour provides an immersive experience into St. Augustine’s rich history and vibrant culture.

Stroll along the oldest street in the U.S., savor regional flavors, and enjoy wine and cocktails while admiring the stunning Spanish architecture.

It’s an accessible and personalized way to explore the historic charms of this captivating coastal city.

Similar Posts