St Augustine Florida’s 2 Top Wine Tours (With Prices)

The 2 Best Wine Tours in St Augustine Florida

St Augustine, Florida, offers more than just its charming colonial streets and ancient fortresses — it’s also a fantastic spot for wine and foodies. Its historic ambiance pairs beautifully with modern tasting experiences, making it an ideal place to explore local flavors and learn about the city’s culinary scene. Whether you prefer a relaxed walking tour combined with history and tastings or a stylish ride in an electric vehicle exploring chic venues, this city delivers memorable experiences.

In this guide, we’ll compare two top-rated wine tours: one that combines a guided walking journey through St Augustine’s oldest streets with wine, cocktails, and food; and another that offers a sophisticated experience traveling in an electric vehicle to exclusive venues. Both tours showcase St Augustine’s unique vibe, but each fits different interests and preferences. Read on to find out which one suits your style best, and get practical tips on booking.

Quick Overview

Our list features two standout wine tours in St Augustine. First, there’s a lively Walking Tour with Wine, Cocktails, and Food that combines history, architecture, and local flavors in a 3.5-hour guided stroll through the oldest streets. Second, the Wine & Dine Tour (Rolling) offers a 3-hour luxury experience traveling in an open-air electric vehicle to some of the city’s most stylish dining spots. Both have excellent reviews, but they serve different travel styles and budgets.

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

At $149 per person, this guided walking tour is perfect if you want a hands-on experience that mixes history, architecture, and local flavors. The tour lasts about 3.5 hours, with checkable starting times, and is rated a perfect 5 out of 5 based on 16 reviews. It begins by exploring Aviles Street, the oldest street in the U.S., where cobblestone lanes and colonial buildings set the scene for a rich historical journey.

What makes this tour stand out is its focus on Florida’s historic coast. Along the way, you’ll enjoy a complementary wine tasting and sip on two handcrafted cocktails, all while hearing stories about St Augustine’s past from your knowledgeable guide. Stops include charming shops, galleries, and restaurants that offer a taste of the city’s vibrant local scene. The highlight is the view of a 17th-century Spanish fortress, adding a dramatic backdrop to your experience.

Guests rave about the guide’s friendliness and knowledge — one reviewer said, “Alex made suggestions for the rest of our trip and was very helpful.” The tour balances history, food, and drink seamlessly, making it a great introduction for first-time visitors or those wanting a flavorful, relaxed way to explore.

Bottom Line: For a lively, informative, and tasty walk through St Augustine’s oldest streets, this tour offers excellent value and a chance to see the city from a unique, historical perspective.

2. Wine & Dine Tour (Rolling)

If you prefer a more stylish experience, for $155 per person, the Wine & Dine Tour (Rolling) takes you on a 3-hour journey in an open-air electric vehicle. It’s perfect for those who want to explore in comfort while enjoying delectable venues in the city. The tour combines sophisticated tastings with insights into St Augustine’s culinary history, with stops at select hotspots known for their unique offerings.

The tour’s appeal lies in its luxury transportation — moving smoothly through the city’s streets, you’ll visit hidden culinary treasures and chic venues that you might not discover on your own. Guests consistently praise the guide, such as one reviewer who said, “Jessica was very knowledgeable and made the experience enjoyable.” This tour is ideal for visitors who want a relaxed yet upscale introduction to the city’s food scene.

The pace allows for plenty of tasting and conversation, making it suitable for couples, foodies, or anyone who enjoys a touch of elegance. The electric vehicle’s quiet ride and exclusive venues create a different vibe from a walking tour—more modern, more stylish, and equally immersive.

Bottom Line: The Wine & Dine Tour (Rolling) offers a polished, comfortable way to taste St Augustine’s culinary gems while learning about its food history. It’s especially suitable if you want to combine sightseeing with an upscale dining experience.

How to Choose

When deciding between these two standout tours, consider your style and what you want to get out of your experience. If you’re a history lover who enjoys walking and exploring at your own pace, the Walking Tour with Wine, Cocktails, and Food provides an engaging mix of storytelling, architecture, and local flavors. It’s perfect for those interested in the city’s past combined with tasting opportunities.

On the other hand, if you prefer a luxurious, relaxed experience in a stylish setting, the Wine & Dine Tour (Rolling) is a smart choice. The electric vehicle offers a smooth ride to exclusive venues with plenty of time for tastings and conversation, making it ideal for couples or those seeking a more upscale outing.

Practical tips: Book early, especially during peak season, as both tours are popular. The walking tour offers flexibility with start times, but check availability beforehand. The rolling tour provides a more contained experience, with fewer logistical concerns about walking distances.

Final Thoughts

Both tours showcase St Augustine’s vibrant flavors and historic charm, but they cater to different tastes. The walking tour excels if you want a lively, story-rich experience with local food and drinks in a small-group setting. Conversely, the electric vehicle tour favors those who enjoy a more relaxed, upscale vibe, visiting the city’s top gastronomic spots without the physical exertion.

For history and food lovers, the Walking Tour with Wine, Cocktails, and Food offers excellent value and a comprehensive introduction. Meanwhile, travelers seeking style and comfort may prefer the Wine & Dine Tour (Rolling), which combines sophistication with local culinary exploration.

No matter your choice, booking early will ensure you secure a spot in these popular experiences. Both options promise an enjoyable way to savor the flavors and stories that make St Augustine a truly special place to visit.