St. Augustine isn’t just the oldest city in the U.S.—it’s also a place where wine lovers can indulge in memorable experiences. Whether you’re cruising along the waterfront with a glass in hand or exploring the city’s culinary scene in a guided tour, this historic town offers a surprising variety of ways to enjoy local wines and food. We’re especially fond of the Wine Tasting Cruise for its relaxed, scenic setting and dolphins that often pop up during the cruise—plus, six different wines sampled in about an hour and a half. It’s a fun, affordable way to see the city from the water and get a taste of local wines, all with a lively crew making sure you’re entertained.
For those who want a more immersive experience, the Wine & Dine Tour is a top pick. It combines sightseeing with tasting at some of the city’s best restaurants, all in a small-group electric vehicle tour. And if you’re after sunset magic, the Champagne Sunset Cruise offers a peaceful way to enjoy the city’s landmarks like Castillo de San Marcos by the light of a stunning sunset—and seasonal lights if you’re visiting during the holidays.
Here’s a quick overview: from cozy boat cruises and guided food and wine tastings to relaxing sunset sailings and mobile wine adventures—each of these tours offers something unique. Now, let’s explore what makes each one special.
1. Wine Tasting Cruise in St. Augustine
At number 1 on our list, the Wine Tasting Cruise delivers a laid-back, scenic way to sample wine while enjoying the beautiful St. Augustine waterfront. This 1.5-hour cruise takes you along the coast, with views of landmarks like Castillo de San Marcos and the Bridge of Lions. It’s a perfect blend of sightseeing and tasting; you’ll sip six different wines, learning about their unique characteristics from the crew.
What makes this tour stand out is its relaxed, intimate setting—cruising on a pontoon boat offers an entirely different perspective on the city. Plus, dolphins, spoonbills, and other wildlife often make surprise appearances, adding a bit of nature’s magic. The onboard bar makes it easy to keep your glass full, and reviews consistently praise the crew’s friendliness and knowledge. One guest sums it up: “The wine was good, and the whole thing was a great time!” It’s particularly well-suited for those who want a quick, affordable, and memorable way to combine water views with wine tasting.
Bottom line: The cruise offers excellent value at just $49 per person, making it an accessible way to enjoy both scenery and wine on a sunny afternoon.
2. Wine & Dine Tour
For around $165, the Wine & Dine Tour hits the mark for its comprehensive approach to the city’s culinary and wine scenes. Over three hours, you’ll ride in an electric vehicle through the historic district, stopping at four to five locally loved restaurants. Each venue features pairings of local cuisine with carefully selected wines, making this a true food lover’s experience.
What sets this tour apart is its insider access to small, neighborhood venues—meaning you’ll get a taste of the authentic local flavor, not tourist-heavy spots. The guide, Mandy, is praised for her knowledge and friendly style, making the journey both educational and enjoyable. Guests often mention the generous food and wine servings, with some saying it’s the best foodie tour they’ve ever had. It’s perfect for those who love gourmet food paired with wine and want a deeper dive into St. Augustine’s culinary culture.
Bottom line: This tour offers good value for a leisurely, intimate experience, ideal for couples or small groups eager to explore local eateries with a knowledgeable guide.
3. St. Augustine Champagne Sunset Cruise w Seasonal Nights of Lights
At number 3, the Champagne Sunset Cruise provides a romantic and peaceful way to take in St. Augustine’s iconic landmarks at dusk. For about 1.5 hours, you’ll glide aboard the Fury Corinthian Catamaran, sipping complimentary champagne, wine, or beer as the sun sets behind the city’s waterfront.
What makes this cruise special is the chance to see sights like Castillo de San Marcos, the St. Augustine Lighthouse, and the Bridge of Lions lit by evening light. During the season, the Nights of Lights add extra sparkle, transforming the city into a glowing spectacle. Reviewers mention the friendly crew and the “beautiful scenery,” making it perfect for a romantic date or a tranquil evening with friends. The limited reviews suggest it’s a quieter, more refined experience compared to the lively boat tours.
Bottom line: If you’re seeking a relaxed, scenic evening cruise with drinks and city views, this experience delivers a memorable sunset and seasonal ambiance for $58.52 per person.
4. Mobile Wine Tasting and Food Pairing Tour
Number 4 on our list, the Mobile Wine Tasting and Food Pairing Tour, combines the best of scenic streets and curated wine tastings. This 2-3 hour experience is perfect for small groups (up to 5), as you ride in a quiet, eco-friendly vehicle through historic St. Augustine while enjoying 4-5 stops featuring wine and food pairings.
What makes this tour special is the blend of personalized service, local history, and carefully selected gourmet accompaniments like charcuterie and desserts. Tour guide Jenna, with her knowledge, brings the city’s stories alive, making it more than just a tasting—it’s an educational experience. Guests say the wines are well-chosen, and the food is plentiful, with some calling it the best wine tour they’ve done. The outside Castillo de San Marcos stop offers a glimpse of the famous fort, adding a historic touch to the day.
Bottom line: This intimate, flexible tour offers excellent value for travelers wanting a personalized experience combining scenic exploration with wine and food.
5. St. Augustine’s Wine, Cocktail and Food Experience
Finally, at number 5, the St. Augustine’s Wine, Cocktail and Food Experience is the longest and most comprehensive tour, lasting about 3.5 hours. For $154 per person, you visit some of the city’s top eateries, sampling food and beverages, including wine, cocktails, and more, while strolling through historic streets.
A key feature is the focus on local cuisine and drinks—from the Castillo de San Marcos to the Huguenot Cemetery, the tour combines history, architecture, and culinary delights. Guests appreciate the variety and quality of the samples, as well as the knowledgeable guide who shares insights into the city’s past. It’s ideal for foodies and history enthusiasts alike, offering a well-rounded taste of St. Augustine’s food and drink scene.
Bottom line: This tour offers excellent value for those wanting a longer, more diverse experience, especially if you enjoy multiple types of food and cocktails paired with city insights.
$154.00 per person
How to Choose the Best Wine Tour in St. Augustine
When deciding on the right tour, consider your budget, schedule, and interests. If you prefer a quick, scenic experience with a laid-back vibe, the Wine Tasting Cruise is perfect. For a deeper dive into local cuisine, the Wine & Dine Tour offers an intimate, small-group experience. If you’re seeking a romantic sunset with drinks, the Champagne Sunset Cruise is your best bet.
For those wanting a personalized wine tasting experience with scenic exploration, the Mobile Wine Tasting combines history, food, and wine in a small-group setting. And if you love a full food and cocktail experience with a touch of history, the Wine, Cocktail, and Food Experience is ideal.
Booking early is recommended, especially during peak seasons like the winter holidays or spring, when these tours tend to fill up fast.
In sum, St. Augustine offers a range of wine experiences that suit every style—from quick scenic cruises to gourmet food adventures. For a relaxed water-bound tasting, the Waterfront Cruise is hard to beat; for a richer culinary journey, the Food and Wine Tour will satisfy. And for romance and sunset views, the Sunset Cruise is a true delight. Whatever your style, these options promise a delicious addition to your historic visit.