Long Island’s North Fork has become a top destination for wine enthusiasts, thanks to its impressive array of vineyards and charming tasting rooms. Whether you’re interested in a relaxed bike ride through scenic backroads, a full-day exploration of multiple wineries, or a private chauffeur-driven tour—all with a focus on local varietals—Long Island offers more than just good wine. These tours provide a taste of the region’s rich viticultural history, stunning landscapes, and the chance to meet passionate wine makers.
In this guide, you’ll find detailed descriptions of four top-rated wine experiences. From a guided bike tour that combines exercise and wine tasting, to a comprehensive private day trip from New York City, each offers something different. We highlight what makes each tour special—including reviews from past travelers, practical details on what’s included, and who each experience is best suited for. Whether you’re a casual wine lover, a dedicated oenophile, or celebrating a special occasion, this guide helps you choose the right Long Island wine tour for your tastes and schedule.
Quick Overview
This list features a variety of tours, including a scenic bike tour perfect for active travelers, an all-day private tour ideal for those who want to explore multiple wineries without the hassle of planning, a group-oriented winery tour that offers a more structured experience, and a luxury half-day private experience tailored for those seeking personalized service. With prices ranging from $100 to over $600, there’s an option to suit a range of budgets and interests.
1. Private Guided Wine Country Bike Tour in Mattituck
The Private Guided Wine Country Bike Tour in Mattituck is a fantastic choice for those who want to combine activity with wine tasting. Priced at $199.00 per person, this roughly 4.5-hour tour takes you along scenic backroads of the North Fork, with options for routes between 12 and 19 miles. The tour is customizable, allowing you to choose a route that fits your pace and stamina.
What sets this experience apart is the chance to enjoy the outdoors while sampling herb-infused oils and fine vinegars at a charming shop in New Suffolk, with lovely views of Peconic Bay. The guides are seasoned and knowledgeable, making the ride both relaxing and educational. Past guests love the intimate setting and the mix of cycling and tasting, with one reviewer noting that the tour was “a perfect blend of exercise and wine.” The bike ride is suitable for most fitness levels, but you should be comfortable on a bike for several hours.
Bottom Line: This tour is best for active travelers who want a personalized, small-group experience that combines scenic views, local flavors, and gentle exercise. While it’s on the pricier side, the customized routes and relaxed pace make it quite a value for a unique day on the North Fork.
2. Full Day Private Long Island Wine Tours from New York City
This Full Day Private Long Island Wine Tour from NYC offers a comprehensive experience for $189.00 per person, lasting around 8 hours. It’s ideal for those who want to leave the planning and driving to the experts while they indulge in the region’s top wineries. The itinerary includes a visit to the Bridge Lane Tasting Room, which is known for its award-winning wines and lively atmosphere.
Guests rave about the relaxed environment and the opportunity to enjoy music, outdoor games, and wine tastings. The tasting room’s reputation for friendly service and a laid-back vibe makes it a popular choice. The tour provides time for photos and additional wine purchases, making it perfect for those who want a blend of relaxation and exploration. The driver is praised for being entertaining and attentive, which enhances the overall experience.
Bottom Line: Perfect for couples or small groups seeking a worry-free, full-day outing that combines multiple wineries with a personal touch. The value is high considering the length and inclusions, but it’s best suited for those who want a guided, hassle-free experience rather than a DIY tour.
3. Long Island Winery Tour
The Long Island Winery Tour is a flexible private option starting at $100.00 per person for 4 to 6 hours. It takes you to several well-known vineyards, including Osprey’s Dominion Vineyards and Duck Walk Vineyards. This tour offers a choice: you can enjoy guided tastings or rent the vehicle to explore on your own and purchase tastings directly at the wineries.
Guests appreciate the mix of wine tasting and scenic views, especially the opportunity to sit on lawns overlooking sprawling vineyards. Past reviews note that the wineries are friendly, and the driver, like “Keith,” is often highlighted as a fun and helpful guide. The flexibility of booking on your own or with tasting options makes this tour adaptable for different budgets and preferences.
Bottom Line: This tour is ideal for travelers who want a customizable experience at a reasonable price. It’s best for those comfortable with self-guided wine tasting or looking for a private driver to handle logistics. It may lack the structured itinerary of larger tours but offers more personal freedom.
4. Half-Day Private Long Island Wine Tour Experience
For those seeking a personalized, intimate experience, the Half-Day Private Long Island Wine Tour Experience is a great pick. Priced at $603.86 per person, it offers a 5-hour chauffeur-driven journey to two top wineries: Osprey’s Dominion and Duck Walk North. This private tour is tailored entirely to your schedule and preferences, starting from your hotel or preferred location.
The experience promises a luxurious, relaxed atmosphere, perfect for celebrating a special occasion or indulging in a personalized wine journey. Past guests highlight the attentive service and exclusive visits, with the flexibility to customize which wineries to visit and how long to stay. Since it’s private and personal, this tour caters best to those wanting full control over their day and a more upscale experience.
Bottom Line: This tour suits travelers with a higher budget who prioritize privacy, tailored itineraries, and a premium experience. It’s less about quantity and more about quality, making it ideal for couples or special celebrations.
How to Choose Your Perfect Long Island Wine Tour
When picking the right tour, start by considering your budget and how much time you have. If you want a full day of tasting and exploring, the private day trip from NYC offers the most comprehensive experience. For those who prefer active fun, the bike tour combines scenic views with gentle exercise, perfect for outdoorsy types. The flexible winery tour is great if you want a more customized or budget-friendly private experience, while the luxury half-day is ideal for celebrating something special with a personal touch.
Think about your fitness level, taste for guided versus self-guided options, and whether you prefer a structured itinerary or more freedom. Booking early is wise, especially in peak seasons (spring and fall), when vineyards are lively with harvest festivals and events.
Final Thoughts
Whether you’re biking past fields of vines, sampling award-winning wines in a lively tasting room, or enjoying a private chauffeur-driven day, Long Island offers memorable ways to experience its wine scene. For active travelers, the bike tour in Mattituck stands out as a unique, fun way to see the countryside. If you prefer a full-day adventure with minimal fuss, the private guided day tour from NYC delivers a rich and relaxed experience. For those seeking privacy and personalized service, the luxury private half-day makes a perfect celebration.
No matter your style, booking early ensures you get the experience you want, especially during peak season. With such a variety of options, Long Island’s wine country is ready to deliver a delightful sip of its best vintages—cheers to planning your perfect trip!