St. Augustine, Florida, offers an unexpectedly rich wine scene woven into its historic streets and scenic coastal charm. Unlike many tourist destinations, this city provides intimate and authentic wine experiences that highlight its colonial past, vibrant culinary scene, and coastal flavors. Whether you prefer a relaxed walk through cobblestone streets sampling local wines and cocktails, or a stylish ride to exclusive eateries with a guided pairing, St. Augustine delivers. This guide explores two standout options: a walking tour that combines history with wine and cocktails, and a chauffeured food and wine pairing adventure in an electric vehicle.
You’ll find details on what each experience includes, what makes them special, and who they’ll suit best—all to help you choose the perfect taste of St. Augustine.
Quick Overview
In this guide, you’ll learn about a guided walking tour with wine, cocktails, and food that explores the city’s historic core, and a luxury chauffeured tour that takes you to upscale venues with expert pairing insights. Both tours are highly rated, but they cater to different styles of tasting—one on foot for a more immersive, historical experience, and the other in style for a relaxed, luxurious outing.
1. St. Augustine: Walking Tour with Wine, Cocktails, and Food
This guided walking tour offers a relaxed way to savor St. Augustine’s historic charm along with a curated selection of Florida’s local flavors. For $149 per person, you’ll spend about 3.5 hours strolling through the city’s oldest streets, enjoying tastings of wine, handcrafted cocktails, and food at thoughtfully selected stops. The tour’s highlight is the chance to walk down Aviles Street, the oldest street in the U.S., lined with galleries, shops, and colonial architecture, all while learning about the city’s fascinating past from a knowledgeable guide.
Participants rave about the blend of history and gastronomy. One reviewer appreciated how the guide “made suggestions for the rest of our trip,” emphasizing the tour’s insider tips. The highlight for many is the complementary wine tasting and the chance to sip two unique cocktails while soaking in views of a 17th-century Spanish fortress. The small group setting ensures a personalized experience, making it ideal for those who want a relaxed pace and meaningful interaction.
This tour is especially perfect if you’re curious about St. Augustine’s history but also want to indulge in local flavors. The walk is manageable for most, but be prepared for cobblestone streets. The only potential downside is the limited time for tasting—if you’re a serious wine enthusiast, you might wish for more options.
Bottom Line: A well-balanced experience blending history, architecture, and small-batch drinks—a good value for those wanting a comprehensive taste of the city’s cultural and culinary heritage.
2. Wine & Dine Tour (Rolling)
This chaffeured food and wine pairing takes your taste buds on a stylish ride through St. Augustine’s best culinary spots. For $155 per person, the 3-hour experience uses an electric vehicle to visit several carefully chosen venues, emphasizing premium food and wine pairings. The tour’s focus on sophisticated hotspots and hidden gems makes it stand out, especially if you enjoy a more luxurious, less walking-intensive outing.
Guests consistently praise the insights into the city’s food history and the chic ambiance. One reviewer noted, “Jessica was an outstanding guide, and the venues were truly amazing,” highlighting the personalized attention and the high-quality experience. The venues typically include upscale restaurants and boutique wine bars, where you’ll learn about pairing techniques and local culinary traditions. The electric vehicle makes for a smooth, climate-controlled ride, perfect for those who prefer comfort or have limited mobility.
This tour is ideal for those seeking a more refined experience with a focus on culinary elegance and expert pairing. Since it’s chauffeured, it suits travelers who want to relax and socialize without the physical effort of walking. The only caveat might be the higher price point relative to a purely walking tour, but the upscale venues and guided insights justify this for many.
Bottom Line: A stylish, informative way to discover St. Augustine’s food scene with a focus on elegance and comfort—perfect for couples or food connoisseurs.
How to Choose
Picking between these tours depends on your interests and style. If you love history, walking cobblestone streets, and sampling regional drinks in a lively atmosphere, the Walking Tour with Wine, Cocktails, and Food offers a relaxed, authentic experience at a reasonable price. It’s especially good if you enjoy stories behind the sights and want a manageable pace.
On the other hand, if you prefer a luxurious, laid-back experience with a focus on upscale venues and expert pairing, then the Chauffeured Food and Wine Tour suits you better. It’s perfect if you’re less keen on walking and more interested in a refined tasting journey without the effort.
Booking early is recommended, especially during peak travel seasons in spring and fall. Check availability and start times, which can vary, to coordinate with your plans. Both tours are in Florida, but each offers a very different vibe—choose based on whether you want to explore on foot or indulge in style.
Final thoughts
Whether you’re a history lover looking to walk through the streets while sipping wine or a connoisseur eager for a chauffeured tasting adventure, St. Augustine has options that deliver memorable experiences. The walking tour is perfect for those who want an intimate, educational journey through the city’s oldest streets, while the luxury vehicle tour is ideal for sophisticated palates seeking comfort and elegance.
If your time in St. Augustine is limited, these tours can serve as a highlight or a perfect introduction to the city’s local flavors. Remember, booking ahead ensures you won’t miss out during busy seasons. Whichever you choose, you’ll come away with a richer appreciation for the city’s unique blend of history, culture, and cuisine.