Wine Tasting Cruise in St. Augustine

If you’re looking for a laid-back way to enjoy St. Augustine’s waterfront, this Wine Tasting Cruise might just be what you need. Even though we haven’t personally taken this particular tour, the glowing reviews and detailed descriptions paint a clear picture of what’s in store. It combines a relaxed boat ride with generous wine samples and some pretty stunning scenery — a combo that many travelers seem to love.

What really catches our attention about this experience? First, the opportunity to see the city and its landmarks from the water, offering a fresh perspective you won’t get from land-based tours. Second, the wine tasting aspect is quite appealing, especially with six different wines rotating throughout the cruise. That said, a point to keep in mind is the relatively short duration of just 90 minutes, which might feel a bit rushed if you’re a true wine enthusiast or want a leisurely pace. This would suit anyone who enjoys scenic views, a bit of wildlife spotting, and a casual, friendly atmosphere—perfect for couples, friends, or anyone looking to unwind on the water.

Key Points

• Beautiful Water Views: Get a fresh perspective on St. Augustine’s skyline and landmarks from the water.
• Multiple Wines: Sample six different wines, with explanations to help you appreciate what makes each one special.
• Wildlife Spotting: Keep an eye out for dolphins, spoonbills, and other local wildlife along the waterway.
• Relaxed Atmosphere: The boat is cozy, shaded, and fully equipped with a bar, making for a comfortable experience.
• Great Value: For $49 per person, you get a lively, guided tour, wine tastings, and scenic views—most say it’s well worth the price.
• Ideal for Adults: Guests must be 21+ with ID; it’s a wine-focused experience, so no kids allowed.

The Itinerary in Detail

Once you arrive at the meeting point, the process is straightforward. There’s a quick safety briefing from the crew, who are described as friendly, knowledgeable, and attentive—adding to the laid-back vibe. The boarding point is at 107 Yacht Club Dr, a convenient spot with free parking nearby, which is always a plus when planning your day.

Cruising the Historic Bayfront

Your hour-and-a-half cruise kicks off by heading along the bayfront of St. Augustine, offering views that include the famous Castillo de San Marcos. This star-shaped fort is a highlight you’ll see from the water, along with the iconic Bridge of Lions. Several reviews mention how special it is to see these landmarks from the water, offering a new angle that’s both scenic and informative.

The Great Cross & Waterway Charm

One of the highlights is viewing the Great Cross from the water—an impressive sight that adds a spiritual and historical touch to the cruise. The route also provides a pirate’s-eye view of the skyline, bringing a fun, adventurous element to your ride. The captain and crew often include interesting commentary about the city, landmarks, and wildlife—making it a more engaging experience than a simple boat ride.

Wine Tasting & Onboard Bar

Here’s where this tour really shines—sampling six rotating wines. The crew describes each wine’s unique qualities, and many reviews highlight how knowledgeable and personable the guides are. Whether you’re a seasoned wine lover or just someone who enjoys a casual sip, the selection is generally appreciated, with reviewers noting that the wines are “very good,” and “the selection was very good.” Two wines from nearby San Sebastian Winery are included, which adds a local touch.

Wildlife & Waterway Sightings

Dolphins are frequently spotted during the cruise, a highlight for many guests. One review mentions, “we saw dolphins multiple times,” which adds a magical element to the experience. The crew even pauses the wine tasting here and there to watch dolphins or other wildlife—showing they truly care about the environment and passenger experience. Birdwatchers will likely enjoy spotting spoonbills or ospreys, making this a fun outing even for nature lovers.

The Crew & Atmosphere

Multiple reviews praise the crew’s friendliness, knowledge, and sense of humor. Someone even called the crew “exceptional” and “funny,” which suggests the tour isn’t stiff or overly formal. Instead, it’s a relaxed environment perfect for chatting, taking photos, and enjoying the scenery.

What to Expect: The Experience from Start to Finish

Meeting & Boarding

Starting at the Yacht Club Dr location, you’ll arrive about 15 minutes early for check-in, which is recommended to ensure a smooth start. Parking is free, and the location is near public transportation, making it accessible. Once on board, expect a safety briefing and a friendly introduction from your guides.

Cruising & Sightseeing

The boat is a 45-foot pontoon called the Osprey, designed to comfortably hold around 38 guests plus crew. It’s fully enclosed with windows you can roll up or down, and it’s shaded—crucial for Florida’s sun. The cruise takes you past key landmarks, giving you ample opportunities for photos and just soaking in the views.

Wine Tasting & Commentary

As you cruise, the crew guides you through each of the six wines, explaining their origins, flavor profiles, and what makes them special. If you’re like many reviewers, you’ll appreciate their expert commentary, humor, and friendly approach. You’re encouraged to sample at your own pace and ask questions, making this feel more like a gathering of friends than a formal tasting.

Wildlife & Nature Moments

Throughout the cruise, the crew’s wildlife commentary enhances the experience. Dolphins often make an appearance, and the guides are quick to point them out and share interesting facts. Some guests mention that the crew even slowed down the boat to allow for wildlife viewing or to pick up litter from the water—showing genuine care for the environment.

End of the Tour

The cruise loops back to your starting point, and most guests report feeling relaxed, happy, and a little more connected to the local landscape. You can then explore the nearby area or grab a bite, knowing you had a fun and scenic water adventure.

Analyzing the Value

At $49 per person, this tour delivers what most reviews suggest is excellent value. For that price, you get a guided boat ride, six wines (including some local options), and wildlife sightings—all packaged into a well-organized, friendly experience. Some might find the wine quality “mediocre but good for the price,” but most reviewers are happy with what they received, especially considering the scenic setting and guided experience.

Given the positive reviews—many guests rated it a perfect 5 out of 5—it’s clear this tour is consistently enjoyable. The fact that most book about 24 days in advance indicates it’s popular among both travelers and locals alike.

Who Will Love This Tour?

This experience is best suited for adults who enjoy scenic water views and wine. It’s perfect for couples looking for a romantic outing, groups of friends wanting a fun social activity, or anyone interested in a relaxed, informative cruise with wildlife spotting. If you’re seeking a longer, more in-depth wine tour or a family-friendly experience, this may not be the right fit, as it’s geared specifically toward adults 21+.

The Sum Up

The Wine Tasting Cruise in St. Augustine offers a delightful way to combine sightseeing, wildlife watching, and wine tasting into one enjoyable activity. The knowledgeable guides, stunning views, and good-quality wines make it a popular choice among travelers, especially those wanting a relaxed, friendly atmosphere. While it’s a fairly short experience, most guests say it’s worth the price for the memories, scenery, and fun vibes.

If you’re looking for an easy, enjoyable way to explore the city’s waterfront from a different angle—plus sip some local wines—this cruise ticks many boxes. It’s best suited for those who appreciate a casual, social experience with a touch of wildlife and scenic beauty. Just remember to book ahead, arrive on time, and bring your camera and sun protection.

FAQ

Are there restrooms on board the Wine Tasting Cruise in St. Augustine?
Yes, the boat is equipped with restroom facilities, making it convenient for guests during the cruise.

Is there parking near the departure point?
Absolutely, there is free parking available at the meeting location, which is a real plus for planning your day.

How early should I arrive?
It’s best to arrive about 15 minutes before your scheduled departure to check in and listen to the safety briefing.

What kind of boat is used for the cruise?
The cruise is on a 45-foot pontoon boat called the Osprey, which is fully enclosed, shaded, and has comfortable seating.

Can I bring snacks or drinks?
Yes, you’re welcome to bring your own snacks or non-alcoholic beverages. No outside alcohol is permitted, but there is a bar onboard for those 21 and over.

What if the weather is bad?
If there’s a small craft advisory or lightning, the tour will be canceled, and you’ll be offered a re-schedule or full refund. The experience is weather-dependent for safety reasons.

All in all, this water-based wine tasting tour combines the best of scenic views, wildlife, and good wines, making it a relaxing and memorable experience for grown-ups looking to enjoy some of St. Augustine’s natural beauty from the water.