The Top 5 St Augustine Wine Tours

St Augustine isn’t just the oldest city in the U.S.—it’s also a surprisingly lively hub for wine lovers. Its scenic waterfront, historic streets, and charming eateries set a perfect scene for sampling local wines and enjoying memorable experiences.

Whether you’re hopping aboard a boat for a wine tasting cruise, exploring the city in an electric vehicle on a food and wine tour, or catching a sunset from a luxurious Champagne cruise, there’s a flavor for every palate.

Personally, I love a tour that combines beautiful views with a relaxed and engaging atmosphere — like the Wine Tasting Cruise in St. Augustine with its dolphin sightings and six different wines.

If you’re wondering which of these tours best suits your style or budget, keep reading. I’ve rounded up the top options that highlight different tastes — from scenic boat rides to intimate guided tastings — so you can pick one that makes your visit truly special.

Quick Overview

For a relaxed, scenic experience, the Wine Tasting Cruise (more details here) offers a delightful way to see St. Augustine from the water while sampling six wines. It’s ideal if you want a casual outing with wildlife sightings and fantastic waterfront views.

If you prefer a guided food and wine adventure through the historic streets, the Wine & Dine Tour (see more here) combines culinary delights with local history, perfect for those who enjoy pairing stories with their bites.

For a romantic evening, the Champagne Sunset Cruise (click here) offers a peaceful ride during sunset, with complimentary drinks and iconic city sights.

Lastly, for a more personalized experience, the Mobile Wine Tasting and Food Pairing Tour (find out more) takes you through historic streets in a private electric vehicle, combining education, taste, and scenic exploration.

And for those who want a comprehensive, foodie-heavy experience, the St. Augustine’s Wine, Cocktail and Food Experience (details here) offers an afternoon of tastings from top local eateries, with plenty of history and lively atmosphere.

1. Wine Tasting Cruise in St. Augustine

At number 1, the Wine Tasting Cruise in St. Augustine stands out for its combination of scenic waterway views and relaxed wine sampling. This 1.5-hour cruise offers a unique perspective of the city’s coastline, passing landmarks like the Castillo de San Marcos and the Bridge of Lions. You’ll enjoy six different wines while aboard a pontoon boat, making it a perfect low-key way to unwind.

The boat tour also provides opportunities to spot dolphins, spoonbills, and other wildlife, adding a touch of nature to your experience.

What makes this tour particularly appealing is its balance of sightseeing and indulgence. The onboard bar and the chance to learn about each wine’s origin and character add educational value, especially if you’re new to wine tasting.

The reviews are glowing, with many visitors praising the crew’s friendliness and knowledge — “crew was exceptional,” one review mentions, and several note dolphin sightings as a fun bonus. The price is accessible at $49 per person, making it a good value for a memorable hour and a half on the water.

Bottom Line: This cruise is ideal for those who want a relaxed, scenic experience with wine, wildlife, and iconic city views. It’s perfect for a romantic outing or a fun group activity.

2. Wine & Dine Tour

Next up is the Wine & Dine Tour, a three-hour guided experience that combines local cuisine with carefully selected wines, all while exploring the historic streets of St. Augustine. For around $165, you’ll enjoy visits to four or five different venues, each offering a full meal-sized portion paired with wines — a true feast for your palate.

The tour is conducted in an electric vehicle, which allows you to move comfortably through the city’s brick-lined streets and iconic landmarks like Flagler College and the Huguenot Cemetery.

What sets this tour apart is the personalized attention from the guide and the insider knowledge about each restaurant’s history and specialties. Reviews mention the “delicious food,” “generous servings,” and a knowledgeable guide who shares compelling insights into the city’s past.

This makes it a great choice for foodies or anyone wanting a deeper dive into St. Augustine’s culinary scene. The tour is all-inclusive, so you don’t need to worry about extra costs.

Bottom Line: Perfect for those who love combining gastronomy with history, and want an intimate, guided experience with plenty of tastings and storytelling.

3. St. Augustine Champagne Sunset Cruise w Seasonal Nights of Lights

Third on our list is the Champagne Sunset Cruise, which offers a relaxed evening aboard the Fury Corinthian Catamaran. During this 1.5-hour ride, you can enjoy complimentary champagne, wine, and beer while taking in panoramic views of St. Augustine’s skyline. The timing coincides with sunset, creating a magical backdrop for romantic moments or peaceful reflection.

The cruise passes key sights like the Castillo de San Marcos, the St. Augustine Lighthouse, and the Bridge of Lions—all framed beautifully by the setting sun.

This tour is especially popular in the fall and winter months when the Nights of Lights illuminate the city. The reviews emphasize the friendly crew and scenic beauty — “views were perfect,” says one. It’s a shorter, more intimate outing that’s ideal for couples or small groups looking to unwind with drinks and stunning scenery.

Bottom Line: If you want a quiet, scenic evening with a touch of elegance, this sunset cruise is a top pick, especially during seasonal lights displays.

4. Mobile Wine Tasting and Food Pairing Tour St. Augustine

Number 4 on our list is the Mobile Wine Tasting and Food Pairing Tour, which offers a private, intimate experience in a quiet electric vehicle. For about $129 per person, this tour combines curated wine tastings at four to five stops with gourmet food pairings, including charcuterie and desserts. It’s designed for small groups (up to five guests), making it very personal and flexible.

What stands out is the tour’s mix of history, local flavors, and scenic driving through historic streets. You’ll also get outside the city walls to see the Castillo de San Marcos from the outside, adding a bit of sightseeing to the tasting experience.

Reviewers highlight the knowledgeable guide and the quality of the pairings, noting that it’s a “great experience for couples or small groups.” It’s a good choice if you want a relaxed, educational experience with personalized service.

Bottom Line: Best suited for intimate groups who value tailored tastings and scenic drives, especially if you enjoy learning about wines and local history.

5. St. Augustine’s Wine, Cocktail and Food Experience

Finally, the Wine, Cocktail, and Food Experience is a comprehensive, 3.5-hour tour that combines food, drinks, and sightseeing. For $154, you’ll visit some of the city’s top eateries, enjoying sample-sized bites and drinks that range from local wines to creative cocktails.

This tour is perfect for those who want an immersive experience of St. Augustine’s vibrant food scene, all while learning about the city’s history.

The tour includes visits to historic sites like the Castillo de San Marcos and the Huguenot Cemetery, with stops to sample food and beverages at each venue. Visitors consistently praise the generous servings and the enthusiastic guide who enriches the experience with historical insights.

This tour is best suited for those who want a full-bodied taste of the city’s culinary and cultural offerings in one lively outing.

Bottom Line: Ideal for food and drink enthusiasts who want a mix of history, city views, and plenty of tastings in a lively environment.

How to Choose the Best Wine Tour in St. Augustine

When selecting your perfect wine experience, consider your priorities: Are you after a relaxing boat ride with wildlife viewing? The Wine Tasting Cruise offers a laid-back water perspective. Or do you want to explore city streets paired with gourmet bites? The Wine & Dine Tour might be your best bet.

Budget-conscious travelers should favor the Waterfront Cruise, while those looking for a more personalized, intimate outing should consider the Mobile Wine Tasting. For sunset lovers, the Champagne Sunset Cruise provides a romantic, scenic finale. And if you prefer a full day of food, drink, and sightseeing, the Wine, Cocktail and Food Experience is hard to beat.

Timing also matters—book early during peak seasons like fall and winter, especially for popular sunset cruises or full-day tours. Think about your interests: active water views, city walking, or private tastings — matching your style will lead to the most satisfying experience.

Final Thoughts

St. Augustine offers a surprising variety of wine-related experiences that highlight its scenic beauty, historic charm, and vibrant culinary scene. For a relaxed, scenic cruise, the Wine Tasting Cruise is hard to beat.

If you’re after an immersive city-based tasting, the Wine & Dine Tour delivers a great mix. And for a romantic sunset, the Champagne Sunset Cruise promises memorable views and a peaceful atmosphere.

No matter your preference, booking early is wise, especially during busy holiday seasons or seasonal events like the Nights of Lights. With these options, you’ll find a tour that fits your style, budget, and schedule — all set for a delicious exploration of St. Augustine’s best wines and scenery.