Sip wine and cocktails with food stops on a 3.5-hour walk through historic St. Augustine
Three Hours and Thirty Minutes
Wine tastings, Cocktails, Food
Explore downtown St. Augustine on a walking tour that pairs wine tastings, cocktails, and shared bites with historic sights along the way.
Ages 21+ only, and IDs are checked before the tour. Parking is not available at the meeting location, so allow extra time to find paid parking.
Full refund at least 1 week before the tour. Date changes must be made more than 48 hours in advance; you can reschedule once at no additional cost. Cancellations within 24 hours are no-shows and not refundable. Tickets are transferable to another party.
The tour is approximately 3.5 hours long and involves walking on historic, sometimes uneven, brick-lined streets.
The tour includes food pairings at three distinct venues, showcasing a variety of dishes.
Dietary accommodations can be requested; please inform the tour operator in advance.
Casa de Vino 57, 57 Treasury Street, St. Augustine, FL 32084
If you're looking for a way to truly understand St. Augustine beyond the surface, this is clearly the experience locals and visitors alike can't stop talking about. The overwhelming sentiment across reviews is that these tours feel less like formal guided experiences and more like exploring with a knowledgeable friend who genuinely loves what they do. Tour guides like Russ, Alex, Stephen, Gary, and Luc consistently earn praise for transforming what could be routine sightseeing into something memorable and personal. People specifically mention the conversational, warm approach that makes hours fly by without feeling rushed or scripted. What really stands out is the variety of tours offered, from walking history tours to specialized food and drink experiences. The guides demonstrate remarkable depth of knowledge about St. Augustine's 450-year history while keeping things entertaining with humor and storytelling. Reviewers repeatedly mention discovering hidden gems and lesser-known stories they would have missed on their own, with many saying they learned things about the city even as locals. The thoughtful touches make a difference too: guides provide follow-up emails with recommendations, accommodate special needs like families with infants, offer water and rain ponchos, and even adjust itineraries on the fly. Several people specifically recommend requesting certain guides by name and booking early in your trip so you can explore the recommended spots afterward. The universal thread? This isn't a forgettable tourist activity but rather an experience that deepens your connection to the city.
Wow, what a treat! This tour was amazing! Alex shared his knowledge with us about the history of St. Augustine and the food and beverage scene. You absolutely should make this tour part of your plan. The drinks and food we sampled were top notch.
Dan Murray
April 2, 2026
Wow, what a treat! This tour was amazing! Alex shared his knowledge with us about the history of St. Augustine and the food and beverage scene. You absolutely should make this tour part of your plan. The drinks and food we sampled were top notch.
Dan Murray
April 2, 2026