Long Island isn’t just about beaches and lobster rolls — it’s also a serious wine region. The North Fork, in particular, boasts vineyards that rival those in California, with some over 50 years old and producing award-winning wines. Whether you’re a casual sipper or a dedicated oenophile, there’s a tour here for you. I’ve been on a few myself, like the Mattituck New York Guided Farm and Wine Country Bike Tour, which combines exercise, scenery, and great wine all in the same trip. It’s a fun, relaxed way to see the countryside, with stops at wineries, beaches, and farm stands. Plus, the photos are included, so you can relive the day later.
For those wanting a more comprehensive look at the region, some tours combine visits to vineyards, orchards, oyster farms, and charming towns. The Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day offers a full day of sightseeing that includes eateries, shops, and even a maritime museum. Whether you prefer a half-day jaunt or a full-day exploration, Long Island’s wine scene is lively, authentic, and worth exploring.
1. Mattituck New York Guided Farm and Wine Country Bike Tour
At number 1, this guided farm and vineyard bike tour offers a blend of physical activity and wine tasting that’s hard to beat. For $139.99 per person, you’ll spend about five and a half hours biking through the beautiful North Fork countryside. The tour includes visits to two vineyards, a beach stop with herb-infused oil and vinegar tastings, and a historic farm stand — one of the original in the area over 50 years old. The bikes are single or tandem, with helmets provided, and professional photos are included to capture your day.
Guests praise this tour for its relaxed pace and personal attention. “The weather was perfect, and the guides made it all so fun,” one reviewer says. The small group size makes it ideal for anyone who wants to explore at a leisurely pace without feeling rushed. You’ll also enjoy tastings of vinegar and olive oil, plus water and refreshments throughout. The combination of scenic views, educational stops, and friendly guides makes this a top pick for active travelers and wine lovers alike.
Bottom line: If you want a unique, physically engaging way to discover Long Island’s wine and farm culture, this tour hits all the right notes.
2. Mattituck Bike Wine Country and Fruit Orchard Tour
At number 2, this bike tour offers a slightly longer, more comprehensive experience for $141.99. Expect about five hours of riding across 13.5 miles of flat terrain, with frequent stops at vineyards, farms, and a fruit orchard. The guide will take you to a vineyard for tastings, support vehicle transports any purchases, and you can even pick your own fruit at the orchard.
This tour is perfect for those who want a taste of everything — wine, fresh produce, and a scenic ride. The guide takes photos during the day, which you can download afterward. Reviews highlight the organization and the tasty lunch options, with one saying, “The infused olive oil and vinegar tastings overlooking Peconic Bay were wonderful.”
Bottom line: This tour is best suited for travelers interested in a diverse, leisurely exploration of North Fork’s farm and wine scene, with plenty of photo opportunities.
3. Guided Farm and Wine Country Bike Tour in Mattituck NY
This guided bike tour costs about $132.99 and lasts roughly five and a half hours. It features stops at boutique and medium-sized vineyards, some with live music depending on the date, plus visits to a beach, farm stands, and a vineyard with a butterfly garden. The tours include herb-infused olive oil and vinegar tastings, with options for single or tandem bikes, helmets included, and sometimes even e-bikes if pre-arranged.
Guests love the personal touch and the diversity of stops, from vineyards to local farms. “The guides are friendly, and the lunch was fantastic,” one reviewer notes. This tour appeals to those who enjoy a mix of wine, music, and nature, with a relaxed, social vibe.
Bottom line: Ideal for lovers of boutique wineries and outdoor fun, with a flexible itinerary that can include live music and local treats.
4. Private Luxury Wine Tours of Long Island Pindar Winery
Number 4 on our list is a private day tour focused on luxury and customization. For $180 per person, spend 6 to 7 hours discovering Pindar Vineyards, one of Long Island’s most scenic and expansive wineries. The tour includes a guided tasting of their premium wines, like Sauvignon Blanc, with behind-the-scenes insights into their production.
This tour is perfect for small groups or couples seeking exclusivity. The optional lunch and the scenic vineyard views make it a relaxing yet informative experience. Reviews highlight the scenic setting and the personalized service. It’s best suited for travelers who want a private, indulgent day rather than a group adventure.
Bottom line: A superb choice for wine aficionados looking for a tailored, intimate experience with expert guidance.
5. Full Day Private Long Island Wine Tours from New York City
Position five features a full-day private tour for $189 per person, covering the entire East End. You’ll visit notable wineries like Bridge Lane and Pindar, with tasting sessions and time to explore at your own pace. The tour lasts about eight hours, making it ideal for those who want to see the highlights without rushing.
Guests appreciate the flexible itinerary and the personalized service, with some mentioning how the wineries are carefully selected to ensure quality and variety. The tour includes tastings, a relaxed lunch, and plenty of time for photos.
Bottom line: Best suited for visitors coming from NYC who want a comprehensive, private experience without the hassle of planning.
6. Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
Our number 6 offers a full-day tour for $559, covering a wide range of sights beyond just wineries. It includes stops at Jamesport, Mattituck, New Suffolk, Southold, and Greenport, with visits to oyster farms, shops, and cultural sites. This is perfect for those who want an in-depth look at the North Fork’s culinary and scenic offerings.
Clients love the personal planning and insider knowledge, which helps turn this into a seamless, memorable experience. The itinerary is flexible, with options to include or skip certain stops to match your interests.
Bottom line: Ideal for travelers with a full day to explore multiple facets of Long Island’s North Fork — wine, food, and local culture.
7. Long Island Wine Tour North Fork Sights Bites Flights Half Day PM
Number 7 is a half-day afternoon tour for $339, focusing on the same core experiences as the full-day but condensed into 4-5 hours. It covers stops in Mattituck, New Suffolk, Southold, and Greenport, with a mix of wine tastings, oyster farms, and boutique shopping.
This option is perfect if you want a taste of North Fork without committing the whole day. Reviewers mention the personalized craft of the tour, which can be tailored to your preferences.
Bottom line: Great for travelers short on time but eager to experience the region’s best sights, flavors, and scenery.
8. Long Island Wine Tour North Fork Sights Bites Flights Half Day AM
The morning version of the previous tour, this half-day for $339 is similarly popular. Starting earlier, it offers the same diversity, with stops at wineries, oyster farms, and Greenport, perfect for those wanting the most out of their morning.
Travelers enjoy the flexible itinerary and the chance to fit the tour into a busy schedule.
Bottom line: Excellent for early risers who want a quick but rich introduction to North Fork’s wine and culinary offerings.
$339.00 per person
9. Long Island Winery Tour
Number 9 is a simple, budget-friendly winery-only option for around $100. It lasts 4-6 hours and includes visits to Osprey’s Dominion and Duck Walk Vineyards. The focus is on tasting the region’s best wines in a private setting with a driver handling transportation.
Reviewers find this tour a good value, especially for those who want to focus solely on the wines and enjoy a relaxed day. The tour offers options for tastings or self-guided visits, which suits varying levels of wine enthusiasm.
Bottom line: Perfect for those on a budget or short on time but eager to sample some top Long Island wines.
10. Half-Day Private Long Island Wine Tour Experience
Number 10 is a highly customizable private tour at $603.86 per person, with a focus on personalized service. It includes visits to two wineries, like Osprey’s Dominion and Duck Walk, with your chosen start time. This is a premium experience suited for couples or small groups wanting exclusivity.
Guests value the tailored itinerary and flexible timing. It’s ideal for special occasions where privacy and customization matter most.
Bottom line: Great for travelers seeking a private, tailor-made wine adventure that fits your schedule.
$603.86 per person
11. Half Day Private North Fork Bike Tour Thru Wine Cntry in Matituck
Our final entry is a private bike tour for up to 6 people at $834. It offers a 3-hour, scenic ride through North Fork’s vineyards, with stops at a charming beach, farm stand, and boutique vineyard.
This is perfect for groups who want a private, active experience. The guide can customize the route from 14 to 19 miles, combining outdoor activity with wine tasting and local flavor.
Bottom line: Excellent for small parties or groups who prefer a private biking adventure with flexible stops.
$834.00 per group (up to 6)
How to Choose Your Perfect Long Island Wine Tour
When choosing among these options, consider your budget, how much time you want to spend, and whether you prefer a relaxed, guided experience or a private, customizable adventure. For instance, if you love biking and want a mix of scenery and wine, the Mattituck Guided Farm and Wine Country Bike Tour is hard to beat. If privacy and luxury are your priorities, the Private Pindar Winery Tour offers a more intimate look.
For those with limited time but a desire for variety, the Half-Day North Fork Sights, Bites & Flights provides a broad taste of the region’s culture, food, and wine. Planning ahead, especially during harvest season or weekends, is recommended — many tours fill up fast.
To sum it up, Long Island’s wine scene offers a range of experiences—from active bike rides to private luxury tastings. If you’re after a lively, social day, the full-day private tours give you the flexibility to customize your adventure. For a more laid-back, scenic option, the guided bike tours are perfect. No matter your style, booking early will ensure you get the best spots—Long Island wine tours are popular year-round, especially during harvest time and fall foliage season. Cheers to discovering the region’s best vintages and hidden gems!