2 Best Wine Tours In St Augustine Florida

St. Augustine, Florida, isn’t just about its historic streets and centuries-old architecture—it’s also a surprisingly vibrant spot for wine and foodies. The city’s unique mix of colonial charm and lively culinary scene makes it perfect for exploring on a guided tour. With options ranging from a relaxed walking experience that blends tales of history with tastings to a stylish, electric vehicle ride through chic venues, there’s something for all wine lovers.

In this guide, we’ll cover the two best wine tours in St. Augustine. Whether you’re interested in a 3.5-hour stroll through cobblestone streets with local food, wine, and cocktails, or prefer a luxurious ride through the city’s top dining spots, these tours offer insights and flavors that will leave you savoring both the drinks and the stories. Plus, with detailed reviews and practical tips, you’ll be able to choose the perfect experience for your trip.

Quick Overview

This list features two standout wine tours in St. Augustine. First is a guided walking tour that combines history, local food, wine, and cocktails, perfect for those who enjoy exploring on foot. The second offers a stylish electric vehicle experience that whisks you between upscale venues, ideal for travelers who prefer comfort and a touch of sophistication. Both tours highlight the city’s culinary charm and offer insights into its rich past, making them memorable choices for any visitor.

For more details on these tours, visit St. Augustine: Walking Tour with Wine, Cocktails, and Food and Wine & Dine Tour (Rolling).

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

This 3.5-hour guided walking tour combines the pleasures of wine, cocktails, food, and history, making it a well-rounded experience for visitors who want to soak in the city’s atmosphere. Starting with a complementary wine tasting, you’ll also sample two handcrafted cocktails while strolling through Aviles Street, the oldest street in the nation. The walk takes you along cobblestone streets lined with shops, galleries, and restaurants, offering plenty of opportunities to absorb the city’s charm.

Guided by knowledgeable locals like Russ or Alex, you’ll learn about St. Augustine’s colonial past while enjoying a variety of local flavors. The tour’s reviews praise the blend of history and hospitality, highlighting the friendly guides and the diverse food and drink selections. The tour’s price of $149 per person reflects its comprehensive nature, covering not just tastings but also the stories behind the city’s architecture and landmarks like a 17th-century Spanish stone fortress.

This tour works best for those who want a relaxed pace with plenty of food and drink and enjoy exploring on foot. The small group size ensures a personal experience, and the mix of history, architecture, and culinary delights provides a perfect introduction to St. Augustine’s coastal charm.

Bottom line: If you’re after an immersive afternoon that combines history, local cuisine, and drinks, this walking tour offers excellent value and memorable moments.

2. Wine & Dine Tour (Rolling)

For travelers seeking a more upscale and comfortable way to experience St. Augustine’s culinary scene, the Wine & Dine Tour (Rolling) is an excellent choice. Priced at $155 per person for a 3-hour experience, it features a luxurious ride in an open-air electric vehicle that transports you between the city’s top dining venues. This tour is designed for those who want to enjoy chic, sophisticated settings with minimal walking, making it ideal for visitors who prefer a relaxed pace.

The tour includes visits to a selection of fascinating hotspots with unparalleled tasting experiences. Jessica, the guide, is praised for her knowledge of the city’s culinary history and her ability to make the experience engaging. The venues are described as amazing, offering a blend of local flavors and hidden culinary treasures. The electric vehicle’s stylish ride allows you to enjoy the sights in comfort while the guide shares stories behind each location.

This experience is well-suited for couples or groups wanting a refined, yet fun, food-focused adventure. Since it’s shorter than the walking tour, it’s also perfect for those with limited time or mobility issues. The reviews reflect high satisfaction, with one stating, “I learned so much from Jessica and loved the venues,” emphasizing the quality of the experience.

Bottom line: For a luxurious, laid-back way to explore St. Augustine’s food scene, this tour offers great value—especially if you enjoy style and comfort along with your tasting.

How to Choose

When deciding between these two wine tours, consider your interest in walking versus riding, your budget, and the type of experience you want. If you prefer a relaxed, in-depth walk with multiple tastings and a lively atmosphere, the Walking Tour with Wine, Cocktails, and Food offers a great day out. It’s perfect if you’re interested in history, architecture, and local flavors all in one.

On the other hand, if you’re looking for an elegant and comfortable experience that emphasizes upscale venues and a stylish ride, the Wine & Dine Tour (Rolling) provides that with less walking and a focus on chic settings. It suits those who prefer a more relaxed pace or have mobility considerations.

In terms of booking, both tours are popular—booking early is recommended, especially during peak season. For those who want a more immersive, historical experience, the walking tour is ideal. If luxury and comfort are your priorities, the electric vehicle ride offers a memorable, fuss-free outing.

Final Thoughts

Both tours showcase St. Augustine’s vibrant culinary scene and historic charm, but they cater to different tastes. The Walking Tour with Food and Cocktails is best for those who want a lively, engaging exploration on foot, while the Wine & Dine Tour (Rolling) appeals to travelers seeking style, comfort, and a more luxurious vibe.

If you’re a history buff, a foodie, or simply curious about the city’s best spots, these experiences are well worth the investment. Consider your personal preferences, timing, and mobility, then secure your spot early—these tours tend to fill up quickly during busy periods. Ultimately, both options promise a delicious taste of St. Augustine, making your visit all the more memorable.