Long Island isn’t just about beaches and seafood; it’s a serious wine destination with a growing reputation for quality vineyards and memorable experiences. The region’s climate, soil, and varied terrain allow for a range of wine styles, from crisp Chardonnays to bold Merlots. Whether you’re a wine novice or a connoisseur, the Long Island wine tours listed here offer something for all.
What makes them stand out? Some focus on biking through scenic vineyards with Mattituck New York Guided Farm and Wine Country Bike Tour, while others combine luxury transport and exclusive tastings, like Pindar Winery’s private tours.
We love how the region offers both active outdoor adventures and luxury relaxations, making it easy to tailor your experience.
Long Island wine tours aren’t just about tasting. Many include farms, beaches, orchards, and historic towns, all within a few miles of each other. Whether you prefer a full-day exploration or a half-day cycling trip, the options are plentiful. Below, we highlight 11 of the best tours, each with its own style and appeal.
- 1. Mattituck New York Guided Farm and Wine Country Bike Tour
- 2. Mattituck Bike Wine Country and Fruit Orchard Tour
- 3. Guided Farm and Wine Country Bike Tour in Mattituck NY
- 4. Private Luxury Wine Tours of Long Island Pindar Winery
- 5. Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
- 6. Full Day Private Long Island Wine Tours from New York City
- 7. Long Island Wine Tour North Fork Sights, Bites & Flights Half-Day PM
- 8. Long Island Wine Tour North Fork Sights, Bites & Flights Half-Day AM
- 9. Long Island Winery Tour
- 10. Half-Day Private Long Island Wine Tour Experience
- 11. Half Day Private North Fork Bike Tour Thru Wine Cntry in Matituck
- How to Choose Your Perfect Long Island Wine Tour
- Final Thoughts
1. Mattituck New York Guided Farm and Wine Country Bike Tour
This guided bike tour offers a relaxed way to explore the North Fork’s farms, beaches, and wineries. For around $140, you’ll enjoy a roughly 5.5-hour trip with helmet use, single or tandem bikes, and professional photos. The itinerary includes visits to 2 vineyards, a beach herb-infused oil and vinegar tastings, and a stop at an old farm stand famous for fruits, pies, and jams.
Tour guides like Mike and Nicole are known for their friendly, informative style, with reviews consistently praising the well-planned, fun-filled day. Guests often mention the beautiful scenery and delicious lunch.
This tour is ideal if you enjoy outdoor activity and want a personalized experience in a small group. The combination of tastings, beaches, and farms makes it varied and engaging. The photos included are a bonus, helping you relive the day.
Bottom line: Perfect for active travelers who want a guided, scenic, and tasty day without the hassle of planning.
2. Mattituck Bike Wine Country and Fruit Orchard Tour
For those who prefer a less strenuous but still scenic experience, this 5-hour bike tour covers about 13.5 miles on flat terrain. It combines vineyard visits, orchard pickings, and farm stops. Highlights include infused olive oil and vinegar tastings, a long-established farm with homemade pies and jams, and a walk through a fruit orchard.
Support vehicles are available for purchases, easing the worry about carrying wine or produce. Guides take professional photos along the way, capturing your memories.
Guests rave about the organized nature of the tour, support, and delicious tastings. The lunch options are flexible, and the overall experience emphasizes local flavors and scenic views. It’s suited for those who want a leisurely ride with multiple tasting opportunities.
Bottom line: Great for foodies and wine lovers who want to combine cycling with farm-to-table experiences.
3. Guided Farm and Wine Country Bike Tour in Mattituck NY
This guided bike tour runs about 5.5 hours, focusing on boutique vineyards, farms, and a beach. Starting with a fitting and options for E-Bikes, the ride then stops at a small vineyard with butterfly gardens and outdoor patios. The tour often features live music, depending on the day. It includes vineyard tastings, visits to farm stands with local produce, and olive oil and vinegar tastings.
The reviews highlight friendly guides and a well-paced tour. It’s ideal if you want to blend wine tasting with local sights and small boutique vineyards. The diversity of stops and the casual atmosphere make this a good choice for relaxed explorers.
Bottom line: Suitable for those who appreciate a personal touch, local charm, and live music while cycling through Long Island’s beautiful landscape.
4. Private Luxury Wine Tours of Long Island Pindar Winery
At number 4, the Pindar Winery private tour offers a customized, intimate experience perfect for special occasions or luxury travelers. Starting with a transfer from Hicksville LIRR Station, you’ll indulge in a guided tasting of Pindar’s signature wines amid scenic 500-acre vineyards.
The tour lasts about 6-7 hours, including stops at Raphael Winery and Lenz Winery, where you enjoy more tastings and insider insights.
Guests love the personalized service, and the scenic landscapes make for memorable photos. The optional lunch at the winery adds a relaxed and luxurious touch. It’s best suited for those who want a private, tailored experience with a focus on high-end wines and scenic beauty.
Bottom line: Ideal for romantic getaways, anniversary celebrations, or VIP treatment in Long Island’s wine country.
5. Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
This full-day tour is tailor-made for curious explorers who want local insights and a comprehensive itinerary. It includes visits to Jamesport’s hidden gems, Mattituck’s wineries, a tour of an oyster farm, and shopping in Southold and Greenport. You’ll sample wines, oysters, chocolates, and small plates, with plenty of time for walking, tasting, and browsing.
Guests appreciate the thoughtful curation of stops and the informative guides who share stories and background. The tour is premium priced at $559 but offers a luxurious, hands-on experience combining culinary delights with wine tasting.
Bottom line: Best suited for food and wine enthusiasts who want a full day immersed in North Fork culture.
6. Full Day Private Long Island Wine Tours from New York City
This private tour offers customizable visits to Pindar Vineyards, Raphael Winery, and more, with a private driver. In about 8 hours, you can enjoy 4-5 tastings, depending on your preferences. It begins with a transfer from NYC, making it perfect for wineries and wine-curious travelers who prefer door-to-door service.
On the day, you’ll enjoy guided tastings and the chance to purchase bottles directly from the wineries. Guests mention the excellent driver, and the flexibility to tailor the day to your taste makes it very appealing.
Bottom line: Excellent for time-pressed visitors seeking a luxury, hassle-free experience with customizable stops.
7. Long Island Wine Tour North Fork Sights, Bites & Flights Half-Day PM
This half-day afternoon tour covers wineries, oyster farms, and Greenport. The curated itinerary is similar to the full-day version but condensed, focusing on local flavor and history. Highlights include visiting a boutique vineyard with outdoor patios and sampling infused oils and vinegars. The walking tour of Greenport offers a touch of local culture with shopping and maritime history.
Guests mention the well-organized nature and delicious tastings, making it a great choice for afternoon explorers. The $339 price includes transportation, tastings, and guidance.
Bottom line: Perfect for those who want a taste of North Fork in the afternoon with a focused, curated experience.
8. Long Island Wine Tour North Fork Sights, Bites & Flights Half-Day AM
Similar to the PM version, this morning tour is ideal for early risers interested in more active sightseeing. It includes stops at the same key locations: Mattituck, oyster farm, Southold, and Greenport. The shorter duration makes it suitable for travelers with tight schedules or those who want to combine a wine tour with other activities.
Guests appreciate the flexibility and local insights from guides. The price remains the same as the PM tour, offering good value for half a day.
Bottom line: Designed for early-day explorers who want a compact, engaging North Fork experience.
9. Long Island Winery Tour
This budget-friendly private tour focuses on visiting key wineries like Osprey’s Dominion and Duck Walk, with tastings included. For around $100, you get an emphasis on the wine experience with comfortable transportation. It suits smaller groups or casual visitors who want a casual, flexible day.
Reviews note that the wineries are beautiful, and the driver is friendly. Since tastings aren’t included at all wineries, you might want to budget for additional purchases.
Bottom line: Great for value-conscious travelers who want a straightforward winery visit.
10. Half-Day Private Long Island Wine Tour Experience
For those who prefer silence and privacy, this private tour offers a personalized 5-hour experience. Starting from your hotel, you’ll visit two wineries—including Osprey’s Dominion with live music—and enjoy personalized tastings. This option emphasizes customization and luxury, at a premium price of over $600 per person.
Guests appreciate the flexibility and personal attention. The high cost reflects the private chauffeur and tailored itinerary.
Bottom line: Best suited for special occasions and luxury seekers willing to spend for a very private, bespoke experience.
11. Half Day Private North Fork Bike Tour Thru Wine Cntry in Matituck
This private bike tour is ideal for up to 6 people, offering a 3-hour ride through the charming North Fork, including stops at a boutique vineyard, local farm stand, and a quiet beach. The up to 19 miles of riding on mostly flat terrain makes it suitable for moderate fitness levels. The tour features herb-infused oils, vinegar tastings, and wine tastings.
The private group format makes it very adaptable. Reviews are sparse but indicate excellent guides and personalized attention.
Bottom line: Perfect for small groups who want an intimate, active excursion blending wine, food, and scenery.
How to Choose Your Perfect Long Island Wine Tour
Picking the right tour depends on your budget, interests, and fitness level. If you love outdoor activity, the bike tours like Mattituck New York Guided Farm and Wine Country Bike Tour are hard to beat. For a luxurious, private experience, the Pindar Winery private tour offers exclusivity and scenic beauty.
Those with limited time might prefer the half-day tours that condense the highlights, while full-day adventures provide a more comprehensive taste of the region.
Consider whether you want guided tastings, or prefer to explore more independently. It’s wise to book early, especially for private and full-day tours, as they tend to fill quickly during peak season.
Final Thoughts
Long Island’s wine scene offers a surprising variety of ways to enjoy its vineyards, farms, and coastal towns. Whether you’re pedaling through scenic vineyards on a bike tour, enjoying a private tasting at a boutique winery, or exploring local farms and beaches on a full-day adventure, there’s an experience suited to your style.
Among the standout options are the balanced, informative bike tours and the luxury private tours for those seeking an upscale escape.
For active travelers, the Mattituck Guided Bike and Farm Tour is a favorite, blending scenery with tastings. If you prefer a more relaxed, premium experience, the Pindar Winery private tour will not disappoint. To get the most out of your visit, book early and decide what fits your interests and budget best. Cheers to discovering Long Island’s excellent wines and charming towns!