St Augustine, Florida, isn’t just a place to soak up centuries of Spanish colonial architecture; it’s also a charming destination for wine lovers. The city’s mix of historic streets, scenic waterfronts, and culinary surprises makes it a surprisingly good spot for wine tours.
Among the options, we particularly like the walking tour with wine, cocktails, and food, which blends history, local flavor, and sips in one engaging package.
Walking down cobblestone streets like Aviles, the oldest street in the U.S., and tasting handcrafted cocktails makes for a real sense of place—and palate. Plus, views of a 17th-century Spanish fortress add a historic backdrop to your wine tasting experience.
For a more relaxed, scenic escape, the Champagne Sunset Cruise offers a unique perspective on the city’s coastal beauty. And if you’re eager to explore beyond the historic district and enjoy a curated culinary journey, the Wine and Dine Pairing Tour combines local eats and wine, all in the comfort of an electric vehicle.
Below, you’ll find detailed descriptions of these top three options, helping you choose the perfect wine adventure in St Augustine.
1. St. Augustine: Walking Tour with Wine, Cocktails, and Food
At number one, this guided walking tour offers a well-rounded experience that combines history, local flavors, and sipping—all in just 3.5 hours. For $159 per person, you get to stroll through the oldest streets in the U.S., including Aviles, where colonial history lives on in every brick and corner.
Your guide leads you through cobblestone streets lined with shops, galleries, and restaurants, providing rich commentary on the city’s past and present.
The tour’s standout feature is the blend of tasting and sightseeing. You’ll enjoy a complimentary wine tasting — a nice way to get introduced to Florida’s coastal wines — and sip two handcrafted cocktails, which could be anything from a classic mojito to a local specialty.
The food stops are thoughtfully arranged to highlight local flavors, making it as much a culinary experience as a historical one.
Plus, you’ll get views of the 17th-century fortress Castillo de San Marcos and colonial architecture, grounding the tasting in the city’s past.
The reviews give it a solid 5/5, with many praising the engaging guide and the relaxed pace that makes it easy to enjoy all aspects.
Bottom Line: Perfect for history buffs and foodies who want an immersive, social, and flavorful introduction to St. Augustine. It’s a bit pricier but offers a well-balanced mix of walking, tasting, and storytelling.
2. St Augustine: Champagne Sunset Cruise w Nights of Lights opt
A different kind of wine experience comes at number two—the Champagne Sunset Cruise. For $59, this 1.5-hour cruise offers a relaxed way to enjoy St. Augustine’s shoreline and majestic sunsets.
The cruise departs on a state-of-the-art catamaran, which features covered seating, a nautical bathroom, and plenty of space to relax while you sip on complimentary drinks, including beer, wine, champagne, sodas, and water.
What makes this tour particularly appealing is the chance to see iconic landmarks like Castillo de San Marcos and the Bridge of Lions from the water, giving a new perspective on the historic city. The sunset views are stunning, especially during the “Nights of Lights” season (November 15 through January 11), when millions of tiny bulbs illuminate the city in an unforgettable display.
The reviews are good, with a 4.3/5 rating, especially praising the ocean breeze and the peaceful ambiance. It’s a superb option for couples or anyone who enjoys scenic views with a chilled drink in hand.
Bottom Line: Ideal for those seeking a brief, scenic escape that combines local sights with a relaxing drink, especially during the holiday lights season. It’s less about deep history and more about the ambiance and views.
3. St. Augustine, FL: Wine and Dine Pairing Tour
For around $155, the Wine and Dine Pairing Tour takes you beyond the historic district into the city’s lesser-known culinary corners. Over three hours, this curated experience features four or more progressive-style stops in areas like Uptown, Anastasia Island, and Lincolnville.
What sets this tour apart is its emphasis on local eateries paired with wine, beer, or artisanal cocktails, offering a deeper dive into St. Augustine’s food scene.
The tour is conducted in the comfort of an electric vehicle, which makes for a relaxed, open-air ride that’s easy on the legs. You’ll sample a variety of dishes—ranging from savory to decadent—each paired to enhance the flavors. Guests often mention discovering “hidden gems” off the beaten path, and the combination of local cuisine and drink creates a relaxed, intimate vibe.
Reviewers don’t have ratings yet, but the price and format suggest a good value for those who appreciate culinary experiences paired with wine in a less touristy environment.
Bottom Line: Best suited for foodies who want a guided, curated look at St. Augustine’s culinary scene, especially if you like to explore neighborhoods beyond the historic core.
How to Choose
When selecting your ideal wine tour in St Augustine, consider your interests and how much time you want to spend. If you’re eager for an immersive history and wine tasting experience, the Walking Tour with Wine, Cocktails, and Food offers a rich blend of storytelling and flavor. For a romantic evening with spectacular views, the Champagne Sunset Cruise provides a relaxed, scenic escape.
If your focus is on culinary discovery and local eats, the Wine and Dine Pairing Tour delivers a curated, neighborhood-hopping experience.
Budget-wise, the cruise is the most affordable and shortest, perfect for a quick taste of the coast. The walking tour is more comprehensive but at a higher price, ideal for history and food lovers. The pairing tour gives a broader culinary view in a comfortable setting, great for foodies wanting a deeper taste of St. Augustine.
Book early, especially during holiday seasons or peak months, to secure your spot on these popular experiences. Each offers a distinct way to enjoy St Augustine’s wine scene—whether on foot, from the water, or through a curated tasting adventure.
Final Thoughts
St Augustine offers a surprising array of wine-related activities that suit different tastes and schedules. The walking tour combines history, food, and drink for an all-in-one experience. The sunset cruise offers breathtaking views and a relaxed vibe, especially during the Nights of Lights. The wine and dine tour provides a taste of the city’s culinary scene in a comfortable, guided format.
For travelers who love history and want to learn about Florida’s coast with a glass in hand, the walking tour is hard to beat. If you’re seeking romance or a peaceful evening with coastal views, the sunset cruise is a perfect pick. For those who want to explore local flavors and neighborhoods, the culinary pairing tour will satisfy your appetite.
No matter which you choose, booking early increases your chances of securing a spot in these popular tours. Each one offers a different way to enjoy the flavors and sights of St Augustine—so pick the one that best fits your interests, and raise a glass to your Florida adventure.