Wine Tasting Cruise in St. Augustine

If you’ve ever wanted to combine a scenic boat ride with a sophisticated wine tasting, then the Wine Tasting Cruise in St. Augustine might just be your perfect afternoon. Promising a blend of beautiful scenery, local wines, and wildlife encounters, this 1.5-hour journey offers more than just your average boat tour.

While it’s notably popular—often booked 24 days in advance—it’s clear that many visitors find it a delightful way to see the city from a fresh perspective.

What makes this experience stand out? First, the chance to see iconic landmarks like the Castillo de San Marcos and the Bridge of Lions from the water is quite special. Second, the onboard wine tasting of six rotating wines ensures you’ll enjoy a variety of flavors, many of which are locally sourced. That said, one thing to consider is the boat’s capacity and comfort, especially on hot days.

But overall, this cruise is an appealing option for those who enjoy relaxed social outings, scenic views, and a touch of local flavor.

This tour suits travelers who appreciate a casual, guided experience with an emphasis on sightseeing and tasting. Perfect for couples, small groups, or anyone looking for a gentle activity that combines nature, history, and wine in a charming setting.

This experience made our article of 15 Best Boat Tours & Cruises In St Augustine.

Key Points

• Unique Water Perspective: See St. Augustine’s highlights from a pontoon boat, offering a different view of the city.
• Wine Sampling: Get a guided tasting of six different wines, including local options, with on-board commentary.
• Wildlife Spotting: Keep an eye out for dolphins, spoonbills, and other local wildlife—many reviews mention dolphin sightings.
• Scenic Landmarks: Cruise past historic sights like the Castillo de San Marcos and the Bridge of Lions, adding context to your visit.
• Relaxing Atmosphere: Small groups (up to 25) and a friendly crew create an intimate, enjoyable environment.
• Value for Money: At $49, the experience combines scenic cruise, guided commentary, and wine tasting, making it a solid deal for the duration.

The Itinerary: What to Expect from Start to Finish

Meeting and Boarding at Florida Water Tours

Your adventure begins at 107 Yacht Club Drive in St. Augustine. The check-in process is straightforward—arrive 15 minutes early for a brief safety talk and to settle in. The boat, a 45-foot pontoon named the Osprey, is fully enclosed with windows that can roll up or down, offering a comfortable environment whether the weather is hot, cool, or a bit breezy.

Authentic review insight: Travelers mention the crew’s friendliness and efficiency, making the check-in smooth. One reviewer said, “the crew was super friendly,” which sets the tone for a relaxed experience.

Scenic Cruise Past Landmarks

Once underway, the boat will glide through the waters near downtown St. Augustine. Expect stunning views of the city’s skyline, including the historic fort and the Bridge of Lions. The captain and crew’s commentary enriches the experience—offering historical tidbits and fun facts about the sights passing by.

Reviewers consistently praise the views, with one noting, “We loved the way the boat slowed down to watch dolphins,” which also highlights the wildlife sightings that are common on this trip. The cruise isn’t just about the sights—it’s about soaking in the atmosphere from a perspective that’s hard to beat.

The Water’s Highlights

As you cruise, you’ll get a Pirate’s eye view of the city’s skyline and observe the craftsmanship of the bridge from below, offering unique angles not visible from land. The captain often slows the boat for wildlife viewing, giving you the chance to spot dolphins and seabirds like spoonbills.

Multiple reviews mention dolphin sightings, which often become the highlight for guests. One happy traveler noted, “We saw dolphins multiple times!” It’s clear that wildlife adds an element of surprise and delight to the journey.

Wine Tasting and On-Board Bar

The core of the tour is the guided wine tasting of six different wines. The wines rotate, so returning guests may sample something new each time, but the focus remains on quality and variety. Knowledgeable guides explain what makes each wine special—whether it’s the local San Sebastian Winery or other regional favorites.

The onboard bar also offers a selection of beer, champagne, canned cocktails, and sangria, which can be purchased with cash or card. Soft drinks, water, and snacks are available for purchase as well—making sure everyone’s needs are met.

Authentic review insight: Guests frequently mention the “knowledgeable crew,” who provide helpful information about the wines and the local area. One reviewer said, “The explanation of the six wines was very knowledgeable,” which adds value beyond just drinking.

Final Views and Return

As the cruise winds down, you’ll return to the dock, with plenty of time to reflect on your experience. The boat’s design ensures comfort, and the small group size keeps it intimate and friendly.

The Value and Practical Considerations

At $49 per person, this cruise offers excellent value when you consider the combination of scenic views, wildlife sightings, and six wine samples. You’re not just paying for a boat ride—you’re investing in a relaxed, guided experience that blends history, nature, and local flavors.

The tour duration—about 1 hour 30 minutes—is perfect for those looking for a quick but satisfying outing. It’s long enough to feel immersive but short enough to fit into a busy sightseeing day.

One frequent comment from reviews is the crew’s friendliness and knowledge, which makes the experience all the more enjoyable. Guests also appreciate the small group size, which fosters a more personal atmosphere.

However, potential travelers should be aware that the boat is not handicap accessible, though if you can walk onto the boat (with a couple of steps), your wheelchair can be accommodated. And on very hot days, seating options might be limited if the boat is full, so arrive early.

Who Will Love This Tour?

This cruise is best suited for those who enjoy relaxed social outings with a scenic backdrop. If you’re a wine enthusiast, you’ll appreciate the guided tasting and local selections. Wildlife lovers will enjoy spotting dolphins and seabirds. It’s also ideal for small groups, couples, or anyone looking for a different way to explore St. Augustine’s waterfront.

People looking for a quick, enjoyable activity that combines sightseeing and tasting will find this experience hits the mark. It’s less about intense history and more about enjoying the moment—so come prepared for a laid-back, enjoyable cruise.

FAQs: Your Practical Guide to the Water and Wine Tour

Are there restrooms on board the Wine Tasting Cruise in St. Augustine?
Yes, the boat is equipped with restroom facilities, so you won’t have to worry about finding a bathroom during the cruise.

Is there parking near the departure point?
Absolutely, there’s free parking available at the departure location, making it convenient for visitors arriving by car.

How early do I need to arrive for the cruise?
You should plan to arrive at least 15 minutes before your scheduled departure time to check in and hear the safety briefing. The tour always departs on time, so punctuality matters.

What type of boat is used?
The tour is hosted on a 45-foot pontoon boat, named the Osprey, which is certified to carry 38 guests plus crew. It’s fully enclosed with windows that can roll up or down, providing a shaded yet open feel.

Is food or drink available onboard?
Yes, a bar offers a selection of wines, beers, champagne, and canned cocktails. Water, soft drinks, and snacks can be purchased, or you’re welcome to bring your own non-alcoholic beverages and snacks—no outside alcohol, though.

Can I bring my own snacks or drinks?
Yes, you’re encouraged to bring snacks or non-alcoholic drinks. Outside alcoholic beverages aren’t permitted, but you’ll find plenty onboard.

Is the boat accessible for people with mobility issues?
The boat isn’t handicap accessible, but if you can walk onto it (with a couple of steps), your wheelchair can be accommodated with prior notice.

What should I bring?
Sunglasses, sunscreen, a hat, bottled water, and perhaps a light jacket or sweater—especially if the weather turns cooler or breezy.

Can kids join the cruise?
Since the minimum drinking age is 21, this tour is exclusively for adults with valid photo ID.

Final Thoughts

The Wine Tasting Cruise in St. Augustine provides a relaxing, scenic way to explore the city from the water while enjoying six local wines and glimpses of playful dolphins. Its friendly crew, intimate atmosphere, and beautiful views make it a memorable addition to any itinerary. It’s perfect for those who enjoy a laid-back, social experience blended with a touch of nature and local culture.

While it’s not a tour for those seeking a deep dive into history or full accessibility, the combination of stunning vistas, wildlife encounters, and quality wines makes it a worthwhile choice for most visitors. Whether celebrating a special occasion or simply craving a different perspective on St. Augustine, this cruise offers a delightful, authentic experience.

In sum, this tour is best for adults who appreciate good wine, serene water views, and the chance to relax while learning about the area’s wildlife and landmarks. It’s a fun, friendly outing that balances entertainment and scenery—making it a standout activity in the historic city.