Wine & Dine Tour (St. Augustine)

Exploring St. Augustine with the Wine & Dine Tour: A Taste of History and Flavors

If you’re seeking a way to enjoy St. Augustine beyond its well-known landmarks, this Wine & Dine Tour offers a delightful mix of history, local cuisine, and carefully selected wines—all wrapped up in a cozy, small-group setting. With a glowing 5-star rating based on 232 reviews, this experience has gained popularity for good reason.

What we love about this tour? First, the chance to explore the historic streets in an open-air electric vehicle—no tiring walking involved. Second, the curated visits to some of the city’s favorite restaurants, which serve up authentic flavors paired with wines you’ll remember. Third, the small group size ensures personal attention from guides who are both knowledgeable and personable.

One thing to consider is that this tour is for adults only (21+), and certain dietary restrictions might not be accommodated. It’s perfect for those who enjoy good food, good wine, and a relaxed, immersive history experience. If you’re a foodie, a wine lover, or simply want to see St. Augustine from a new angle, this tour is likely to satisfy.

Key Points

• Small group size enhances interaction and personalized service
• All food and wine pairings are included, creating a comprehensive full-meal experience
• Chauffeured electric vehicle makes touring comfortable and eco-friendly
• Multiple venues showcase local culinary gems and hidden favorites
• History and sightseeing are woven into the journey, with pass-by landmarks like Flagler College
• Advance booking is recommended, often booked 24 days ahead

An Authentic Taste of St. Augustine

This tour is a wonderful way to get a full sense of what makes St. Augustine special—its history, its lively neighborhoods, and its vibrant culinary scene. For about three hours, you’re transported through the historic district in a quiet, battery-powered open-air vehicle, allowing you to relax and take in the sights without the fatigue of walking. The small group (maximum of 8 travelers) makes it feel more like a local outing than a generic tour, with plenty of chances for questions and conversation.

The Itinerary Breakdown

The experience includes visits to four to five venues, each carefully selected to highlight local flavors and the city’s warm hospitality. These aren’t just quick stops; they are full-fledged tasting sessions that can rival a substantial lunch or dinner. The guide, a licensed and knowledgeable local, shares insights into each venue’s history and what makes their dishes special.

You start at 8 Carrera St, the meeting point for this culinary adventure. From there, the guide whisks you through the streets, passing iconic sites like Flagler College and the Huguenot Cemetery, offering snippets of local history along the way. Every venue has been praised for excellent service and the quality of food and drink, with reviewers mentioning everything from delicious desserts to hearty, well-paired wines.

The Venues and Tastings

While the specifics depend on the day, reviewers consistently mention the quality and generosity of each stop. Expect to sample a variety of local cuisines, paired thoughtfully with wines—many of which are selected for their perfect complementarity. One reviewer called it a “feast that rivals a nice size lunch or dinner,” emphasizing the richness of the experience. For those with wine preferences, beer can be substituted upon request, adding flexibility.

Each stop offers a different vibe, from casual neighborhood spots to more refined venues, giving you a well-rounded taste of local dining. Judy, Jessica, Kimberly, and Rachael—our guides—are frequently praised for their friendliness, knowledge, and ability to weave stories into the tasting experience. One reviewer even mentioned that Jessica ended the tour singing a song, adding a fun, memorable touch.

The Transportation and Group Size

The electric vehicle provided is not only eco-friendly but also makes the ride smooth and comfortable, especially in the hot weather that can greet visitors. The small group guarantees that you won’t feel lost in a crowd, and guides can tailor their commentary based on your interests.

The Value and Price Point

At $165 per person, the tour offers excellent value considering the all-inclusive food and wine, private transportation, and personalized experience. Multiple reviewers have called it “worth every penny,” highlighting the quality of the food, the friendliness of guides, and the intimate atmosphere. Compared to other sightseeing options, this tour blends entertainment, education, and indulgence into a seamless package.

The Reviews Say It All

Reviewers consistently praise the guides, especially Judi, Mandy, Jessica, Kimberly, and Rachael, for their personable approach and wealth of local knowledge. One even mentioned how the tour helped uncover hidden gems they wouldn’t have discovered on their own.

Many reviews highlight the generous portions, with some describing it as a “full meal,” and appreciate the opportunity to learn about St. Augustine’s history in a relaxed setting. The combination of good food, great wines, and lively commentary makes this a memorable experience.

Who Is This Tour Perfect For?

This experience suits travelers looking for a leisurely, adult-oriented way to explore St. Augustine’s culinary scene and historic streets. It’s ideal for those who appreciate quality food and wine, enjoy small-group tours, and want an authentic experience that’s both educational and fun. If you dislike large crowds or have specific dietary restrictions, note that accommodations may be limited.

For history buffs, this tour offers a taste of the city’s past alongside its flavors. For couples celebrating special occasions like birthdays, the tour’s intimate nature and personalized service make it extra memorable.

Practical Details

The tour lasts about three hours, making it a perfect half-day activity. It starts at 8 Carrera St and ends back at the same point, eliminating the hassle of transportation logistics. With most travelers booking around 24 days in advance, it’s wise to reserve early, especially during peak seasons.

All food and wine pairings are included, with options to swap beer if preferred. Not included are gratuities, but reviewers universally agree that tipping guides who work hard and make the experience special is appreciated.

Since the tour is conducted in good weather, rain or shine, you’ll want to dress comfortably and be prepared for the outdoor ride. The maximum group size of 8 ensures personalized attention, making it easier to ask questions and engage with your guide.

FAQs

Is this tour suitable for vegetarians or those with dietary restrictions?
While most dietary needs cannot be guaranteed, it’s best to notify the company about severe allergies or restrictions. Varying menus might not cater to all specific diets, but the focus remains on local cuisine and wine pairing.

Can I bring children or infants?
No, this tour is exclusively for those 21 and older, and pets are not allowed.

What is included in the price?
All food and wine pairings, private transportation, and guided commentary are included. Beverages can be substituted with beer upon request.

How many stops are there, and how long does each last?
There are 4 to 5 venues visited during the 3-hour tour. Each stop offers a full tasting experience that can rival a meal, with generous servings and paired wines.

Do I need to book well in advance?
Yes, most travelers book around 24 days ahead, and the small group size means availability can fill quickly, especially during peak seasons.

What should I wear?
Comfortable clothes suitable for outdoor riding and walking are recommended. The electric vehicle provides some protection from the sun, but bring sunscreen and sunglasses.

Final Thoughts

The Wine & Dine Tour in St. Augustine offers a relaxed, engaging way to explore the city’s streets, flavors, and history all at once. It’s crafted for those who love good food, excellent wines, and authentic local stories, all delivered by guides who genuinely care about making your experience memorable.

If you’re looking for a fun, intimate, and delicious way to see St. Augustine, this tour is a smart pick. It balances education, indulgence, and entertainment in a way that leaves most guests eager to revisit or recommend to friends.

Whether celebrating a special occasion or just wanting to treat yourself, this experience promises a flavorful journey through one of America’s oldest cities—without feeling like a typical tourist trap. Just arrive hungry, ready to sip, savor, and learn a little along the way.

Happy tasting and exploring!