Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience Long Island wine with a private, 4-hour tour including tastings at Osprey and Duck Walk wineries, live music, and flexible pickup options for $295.

The Long Island Winery Tour offers a 4-hour private journey through the lush vineyards of the North Fork, with inclusive tastings at Osprey Winery and Duck Walk Winery. Priced at $295 per person, this tour combines scenic views, expert guidance, and the chance to savor some of the region’s most renowned wines. With a pickup service from any location on Long Island and private transportation, it caters to those seeking a relaxed, personalized wine adventure.
A notable strength of this tour is its flexibility; you can bring your own lunch or purchase one for an extra fee, and the tour features live music on weekends that enhances the atmosphere. The small group setting ensures an intimate experience, making it ideal for families, friends, or couples wanting to enjoy the North Fork’s vineyards in comfort. While the price is higher than some group tours, the private aspect and inclusion of tastings and transportation justify the cost for many wine enthusiasts.
You can check availability for your dates here:

The North Fork is famous for its breathtaking vineyards and sprawling green landscapes. This tour takes you through some of the most picturesque parts of Long Island, where rows of lush vineyards stretch across rolling hills. The scenery provides a tranquil backdrop for wine tasting and photo opportunities, allowing visitors to fully appreciate the region’s charming rural environment.
Both Osprey Winery and Duck Walk Winery are renowned for their long-standing reputations. These stops highlight Long Island’s reputation for crafted wines, showcasing the area’s famous varietals and regional charm. Travelers can expect to enjoy their tastings while gazing over beautiful vineyard views, making the experience both flavorful and visually pleasing.

Unlike larger, group-focused tours, this private experience offers personalized attention from a professional, suited driver who speaks English. The private transportation ensures a smooth, comfortable journey without the rush or noise of large groups. The flexibility in scheduling and the ability to customize the tour—such as opting for just one winery—adds to the appeal.
The live music on weekends elevates the ambiance, creating a casual, fun vibe while sampling wines. The small group size guarantees a more intimate and relaxed environment, perfect for family outings or small celebrations. The pickup service extends across Long Island, though travelers in Nassau County should allow extra time for travel to the wineries.
The stops at Osprey Winery and Duck Walk Winery are scheduled to include 3-5 tastings at each location. Visitors can expect to sample a variety of wines crafted on-site, gaining insights into the regional wine-making process. These wineries are well-regarded for their diverse wine selections and scenic vineyard settings.
At either winery, the tasting experiences are designed to be relaxed and enjoyable, with the option to learn about different varietals and wine-making techniques. The tastings are included in the tour price, providing good value for the quality and variety offered.
More Great Tours NearbyOne of the tour’s practical advantages is the option to bring your own lunch, which can be enjoyed during the tour or at the winery. Alternatively, an additional fee can be paid if you wish to buy lunch at the winery or nearby. This flexibility allows for a personalized experience, whether you prefer a picnic-style meal or a catered option.
Since the tour lasts 4 hours, this gives ample time to sip wines, enjoy live music, and soak in the vineyard views without feeling rushed. The ability to customize the experience makes it suitable for a variety of preferences, from casual wine lovers to those seeking a more indulgent day.
The pickup service is available anywhere on Long Island, making it convenient for visitors staying in different parts of the region. For locations further west in Nassau County, expect additional travel time to reach the wineries, which is a consideration for planning your day.
The 4-hour duration is ideal for a leisurely afternoon. The tour is wheelchair accessible, ensuring that guests with mobility needs can enjoy the experience comfortably. The private group setting ensures a calm environment, free from the noise and hustle of larger tours.
At $295 per person, the tour is priced for those looking for a more exclusive, personalized experience. The cost includes taxes, wine tastings, live music, and private transportation. However, driver gratuity is not included, which guests may wish to add at the end of the tour.
While more expensive than some group tours, the private nature, quality of wineries, and flexibility offered provide good value for visitors wanting a tailored, relaxed wine tour. This experience is best suited for small groups seeking comfort, exclusivity, and a scenic vineyard visit.
The Long Island Winery Tour is operated by Winston Wine Tours, a provider known for servicing over 500+ wine tours across the region. Their professional, suited driver and English-speaking guides ensure a smooth and enjoyable experience.
The option to reserve now and pay later offers flexibility for planning, and the full refund policy—cancel up to 24 hours in advance—adds peace of mind. Their commitment to personalized service makes this tour a reliable choice for wine lovers wanting an intimate, top-quality experience.
The Long Island Winery Tour provides a luxurious, flexible experience for those wanting a private day on the North Fork. With a focus on scenic views, quality tastings, and personalized service, it appeals to small groups, couples, or families who value comfort and exclusivity.
While the price point may be higher than some group options, the inclusion of tastings, private transport, and live music on weekends** make it a compelling choice. It’s especially suitable for visitors who want to avoid large crowds and enjoy a tailored wine adventure with stunning vineyard scenery.
What is included in the tour?
The tour includes wine tastings at two wineries, live music on weekends, private transportation, and a professional, suited driver. Taxes are also covered.
Can I customize the number of wineries visited?
Yes, there is a value option that features only one winery if preferred.
Is lunch included in the tour?
No, lunch is not included but you are welcome to bring your own or buy lunch at an additional cost during the tour.
How long is the tour?
The tour lasts 4 hours, providing plenty of time for tastings, sightseeing, and relaxation.
Is the tour accessible for wheelchairs?
Yes, the tour is wheelchair accessible.
What is the price for this experience?
The cost is $295 per person, with taxes included, but driver gratuity is not included.
What days is live music available?
Live music is available on weekends, adding a lively touch to the vineyard visits.
Where does the tour pick up from?
The tour offers pickup from any address in Long Island, but additional travel time applies for Nassau County locations.
Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.
Who operates this tour?
The tour is provided by Winston Wine Tours, known for their extensive experience in organizing wine experiences.