St. Augustine, FL: Wine and Dine Pairing Tour

If you’re planning a trip to St. Augustine, Florida, and want to see beyond the historic streets, this Wine and Dine Pairing Tour offers a unique way to experience the city’s lesser-known neighborhoods while indulging in fantastic food and drink. We haven’t taken the tour ourselves, but based on detailed descriptions and reviews, it promises a delightful combination of culinary discovery and relaxed sightseeing, all in just three hours.

What makes this tour especially appealing are two standout features: first, the chance to explore vibrant neighborhoods like Uptown, Anastasia Island, and Lincolnville — places that often fly under the radar for travelers. Second, the thoughtful pairing of each food stop with wine, beer, or artisanal cocktails, elevating each tasting into a memorable experience.

However, a potential consideration is the limited dietary accommodations—last-minute requests for vegan, gluten-free, or other special diets aren’t possible, so travelers with strict restrictions should plan accordingly. This tour is best suited for those who enjoy a relaxed pace, love good food and drink, and want a guided look into some of the city’s more authentic neighborhoods.

Key Points

• Off-the-beaten-path neighborhoods: Explore areas beyond the historic district that are full of local flavor.
• Progressive dining experience: Four or more stops, each with a seated tasting paired with drinks.
• Comfortable transport: Ride in a quiet, open-air electric vehicle, making it easy to enjoy the scenery.
• Expert guidance: A fully licensed guide leads the way, sharing insights about the city and its culinary scene.
• Duration and timing: Approximately three hours, usually in the afternoon, perfect for a relaxed exploration.
• Limited group size: Small groups of up to 8 participants ensure an intimate experience.

You can check availability for your dates here:

A Practical Overview of the St. Augustine Wine and Dine Tour

This tour offers a different lens on St. Augustine — one that’s less about history and more about local flavors. In three hours, you’ll visit multiple neighborhoods, enjoy at least four thoughtfully curated stops, and sample food expertly paired with beverages. The experience emphasizes authenticity and quality, making it appealing to foodies and wine lovers alike.

The Transportation: Electric Vehicle Comfort

One of the standout features is the electric vehicle — a relaxed, open-air ride that allows you to comfortably glide between stops. Unlike walking tours, which can be tiring in Florida’s heat or rain, this mode of transport keeps you cool and relaxed, yet close enough to enjoy the sights and sounds of each neighborhood.

Reviewers praise this aspect, noting that the electric vehicle provides a “comfortable, quiet ride” that makes the whole experience feel like a casual, social outing rather than a hurried tour. It’s a great way to absorb the local atmosphere without fatigue.

The Itinerary: From Uptown to Anastasia Island and Lincolnville

While the specifics of each stop are not exhaustively detailed, the tour’s highlights include visits to areas beyond the historic district, such as Uptown, Anastasia Island, and Lincolnville. These neighborhoods are known for their vibrant local culture, colorful storefronts, and community charm.

Each stop offers a seated tasting, with delicious bites that range from savory to sweet, complemented by seasonal drinks—whether wine, beer, or artisanal cocktails. The description suggests a focus on local culinary gems rather than tourist traps, which adds value for those seeking authentic experiences.

The Food and Drink: Well-Paired, Thoughtful Tastings

What sets this tour apart is the emphasis on pairing. Each course is carefully matched with a drink, enhancing the flavors and making every bite feel special. From the reviews, we gather that the wine selection is excellent and the delicious food and tapas are highlights.

While the exact menu isn’t provided, the emphasis on quality pairings indicates a curated selection designed to elevate each tasting. Expect a progression from savory starters to decadent desserts, all enjoyed in a relaxed setting.

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Guidance and Group Size

With a small group limit of 8, you can expect a more personalized experience. The fully licensed guide will not only narrate about the city’s culinary scene but also facilitate conversations, answer questions, and share local insights. The multilingual support (English and Spanish) also broadens accessibility.

Pricing and Value

At $155 per person, the tour is a fair investment in a curated, intimate experience. While it’s not a budget option, the price covers delicious tastings, expertly paired drinks, transport, and a knowledgeable guide. Considering that each stop involves seated tastings in unique venues, the value is comparable to a private food experience—without the hefty price tag.

Practicalities and Considerations

• Meeting Point: On the steps of the Grace United Methodist Church, a central and recognizable spot.
• Duration: Three hours, usually in the afternoon, making it a perfect addition to an active day.
• Weather: Tours go out rain or shine. While most seating is indoors, you’ll stroll between venues, so bring an umbrella if rain is forecast.
• Dietary restrictions: Require 24-hour notice, but last-minute special requests cannot be accommodated. This is important for those with allergies or special diets.

Who This Tour Is Best For

This experience is ideal for culinary adventurers who enjoy pairing food and drinks and want to explore neighborhoods beyond the typical tourist spots. It’s perfect for small groups seeking an intimate, guided outing that combines local charm with gourmet bites. It’s also well-suited for those who prefer vehicle transport over walking, especially in the warm Florida climate.

However, if you have strict dietary needs or prefer a tour strictly focused on history, this may not be the best fit. Also, those under 21 are not permitted, as alcohol is served at each stop.

The Sum Up: Who Will Get the Most Out of This Tour?

This wine and dine tour offers a balanced mix of local exploration and gourmet pleasure. It’s best for food lovers who want a relaxed, guided experience that reveals a different side of St. Augustine—its neighborhoods, community, and culinary creativity. For travelers seeking a social, intimate setting with excellent food and drink, this tour delivers in spades.

While it’s not a comprehensive history lesson, it offers authentic tastes and a beautiful setting—all in a well-paced, small-group format. Whether you’re celebrating a special occasion or just want to experience St. Augustine in a new way, this tour provides a memorable, flavorful snapshot of the city’s vibrant culinary scene.

FAQ

What is included in the tour?
The tour includes delicious food tastings, paired with wine, beer, or artisanal cocktails, along with chauffeured transportation and a licensed guide.

How long is the tour?
The experience lasts approximately three hours, usually in the afternoon, ideal for a leisurely exploration.

Where do I meet the tour?
The meeting point is on the steps of the Grace United Methodist Church, a central location in town.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans shift.

Is this tour suitable for children?
No, it’s not suitable for anyone under 21, as alcohol is served at each stop.

Are dietary restrictions accommodated?
They require 24-hour advance notice for dietary restrictions, but last-minute requests for special diets aren’t guaranteed.

Is weather a concern?
Tours go out rain or shine. While most seating is indoors, expect some strolling between venues, so bring an umbrella if needed.

What language(s) is the guide available in?
Guides are available in English and Spanish.

How many people will be in my group?
The group is limited to 8 participants, ensuring a more personal experience.

What is the price?
The tour costs $155 per person, which covers tastings, drinks, transportation, and guiding.

Whether you’re a local foodie or a visitor eager to see the city’s quieter neighborhoods, this Wine and Dine Pairing Tour offers a tasteful way to experience St. Augustine’s culinary diversity—one delicious stop at a time.

You can check availability for your dates here: More Great Tours Nearby