St Augustine, Florida, might be best known for its Spanish Colonial architecture and charming cobblestone streets, but it also has a surprisingly vibrant wine scene. The city’s small size and historic neighborhoods make it an ideal place to explore wine, cocktails, and local flavors without feeling overwhelmed. We particularly like the Walking Tour with Wine, Cocktails, and Food, which combines history and tastings in a relaxed stroll through the city’s oldest streets. It offers a perfect way to soak up the atmosphere while sampling Florida’s local tastes, all guided by someone who can share the stories behind the sights.
If you’re looking for a sunset experience, the Champagne Sunset Cruise with Nights of Lights makes for a memorable evening on the water, especially during the holiday season when the city is beautifully lit. For those who want a more immersive culinary adventure, the Wine and Dine Pairing Tour offers a chance to explore beyond the historic district and enjoy multiple stops in stylish electric vehicles.
Here’s a quick overview of the top wine experiences in St Augustine: from walking tastings that include food and cocktails, to scenic sunset cruises with drinks in hand, and gourmet pairing tours that take you across different neighborhoods. Each offers a unique way to enjoy the city’s flavors. Now, let’s explore each one in detail.
1. St. Augustine: Walking Tour with Wine, Cocktails, and Food
At number one, this guided walking tour is a fantastic way to combine history, local cuisine, and beverage tastings. Over 3.5 hours, you’ll stroll down Aviles Street, the oldest street in the U.S., soaking up the architecture and stories while enjoying a complementary wine tasting and craft cocktails. The guide points out historic landmarks like the 17th-century Spanish fortress, giving context to your sips and bites along the way.
What sets this tour apart is its focus on Florida’s historic coast flavors paired with rich stories about the city’s past. You’ll stop at shops, galleries, and restaurants, all while sampling local wines and handcrafted cocktails. The small-group size means more personalized attention, and with an average rating of 5/5 based on 18 reviews, it’s clearly a crowd favorite. Many say the mix of history, food, and drinks creates “a perfect afternoon” for both first-time visitors and seasoned travelers.
Bottom line: This tour is ideal for history lovers who want a relaxed, interactive experience that combines tasting and storytelling. It’s a bit more expensive but offers a comprehensive taste of St. Augustine’s culture and flavors.
2. St Augustine: Champagne Sunset Cruise w Nights of Lights opt
For around $59, the Champagne Sunset Cruise offers 1.5 hours of relaxation on a modern catamaran. This experience is perfect if you want to combine scenic views with a casual drinks experience, especially during sunset or the magical Nights of Lights season (November 15 through January 11).
You’ll cruise along the coast, feeling the ocean breeze while enjoying complimentary beer, wine, champagne, sodas, and water. The boat features covered seating and a nautical bathroom, making it comfortable even if the weather shifts. The highlight is the opportunity to see iconic landmarks like Castillo de San Marcos and the Bridge of Lions from the water, with the sunset casting a warm glow over the city.
This tour is well-reviewed, with a 4.3/5 rating from 4 reviews, emphasizing the relaxing vibe and spectacular views. It’s especially suitable for those wanting a romantic or mellow evening without the hassle of land-based tours. During the Nights of Lights, it becomes even more enchanting, adding a layer of festivity.
Bottom line: Best suited for couples, small groups, or anyone wanting a tranquil way to enjoy St. Augustine’s skyline. The cruise offers great value for a short, scenic, drink-filled escape.
3. St. Augustine, FL: Wine and Dine Pairing Tour
Priced at $155, the Wine and Dine Pairing Tour is a more gourmet-focused experience. Over three hours, you’ll enjoy four or more tasting stops across different neighborhoods like Uptown, Anastasia Island, and Lincolnville. The tour is conducted via a confortable electric vehicle, which means no walking fatigue and a relaxed pace to savor the cuisine.
What makes this tour special is how it goes beyond the historic district to uncover hidden culinary gems. Each stop pairs local wines, beers, or artisanal cocktails with savory, decadent treats. Guests love how this “progressive” dining experience reveals St. Augustine’s culinary diversity away from tourist hotspots. The tour’s focus on pairing and discovery appeals to foodies eager to explore Florida’s local flavors and lesser-known restaurants.
While reviews are pending, the value here is evident in the variety of stops and the focus on gourmet pairings. It’s suited for those who want a culinary adventure with a comfortable ride and a chance to explore the city’s diverse neighborhoods.
Bottom line: Perfect for food and wine lovers who want to combination of sightseeing and gastronomic discovery. It’s a bit pricier but offers a unique, behind-the-scenes look at St. Augustine’s culinary scene.
$155 per person
How to Choose Your Perfect Wine Experience
When selecting the best wine tour in St. Augustine, consider your budget, interests, and the type of experience you crave. If you love history and a social atmosphere, the walking tour provides a relaxed, educational sip through the past. For a romantic evening or photo-worthy sunset, the Champagne cruise offers scenic tranquility on the water. If you’re a foodie looking for an immersive, multi-stop tasting adventure, the Dine and Wine Pairing Tour takes you beyond the usual and into local culinary secrets.
Think about how much time you want to dedicate and whether you prefer walking, cruising, or riding in comfort. Booking early is advised, especially during festive Seasons like Nights of Lights, which draw many visitors.
Final Thoughts
St Augustine offers a surprising variety of wine and food experiences that cover everything from historic strolls to scenic cruises and gourmet tastings. The Walking Tour with Wine, Cocktails, and Food stands out as a balanced choice for history and flavor lovers. The Sunset Cruise is perfect for those who want a relaxed, scenic drink with a view, while the Wine and Dine Pairing Tour appeals to culinary explorers.
No matter which experience you choose, you’ll find that St Augustine’s charm extends beyond its streets—into every glass and bite. Book early, especially in the holiday season, and enjoy discovering the city’s best flavors in style.