6 Most Highly Rated Wine Tours In Long Island

The 6 Best Wine Tours in Long Island

Long Island isn’t just about beaches and seafood; it’s also a surprisingly diverse wine region that offers a variety of ways to experience its viticultural charm. The North Fork in particular has become a favorite for wine lovers seeking a laid-back, authentic experience away from crowded tourist spots. With rolling vineyards, boutique wineries, and scenic rural roads, it’s a perfect place to explore by bike, private car, or on guided tours.

We’ve put together this list based on reviews, ratings, value, and unique experiences—from a private guided bike tour that combines exercise and tastings, to a full-day private experience that takes you through multiple vineyards and local sights. Each offers something different, whether it’s the intimacy of a small-group tour or the flexibility of a customizable itinerary.

In this guide, you’ll find detailed descriptions of each tour, including what makes them stand out, the kind of experience you can expect, and practical tips to help you pick the best option for your plans. Whether you’re after a leisurely tasting, a scenic bike ride, or an in-depth exploration of the North Fork, this list has you covered.

Quick Overview

The best wine tours in Long Island range from half-day, private, and customizable experiences to full-day adventures. Some focus on active exploration, like the private guided bike tour, while others deliver a comprehensive itinerary covering multiple vineyards, local attractions, and culinary stops. Prices vary from around $100 for a simple day trip to over $600 for a luxury private experience, with options for tasting all types of wines—from crisp whites to bold reds.

Most tours include visits to renowned wineries like Pindar Vineyards and Osprey’s Dominion, with some adding on stops at oyster farms, botanical gardens, or artisanal shops. Whether you want a relaxed, guided experience or a more active, self-curated exploration, these tours offer a taste of Long Island’s rich wine scene in ways that highlight its scenic beauty and local craftsmanship.

1. Private Guided Wine Country Bike Tour in Mattituck

This Private Guided Wine Country Bike Tour combines physical activity with some of the region’s best boutique wineries. Over approximately 4.5 hours, your seasoned guide will lead you along winding backroads, close to the Peconic Bay, with options to customize routes of 12, 14.5, 16, or 19 miles. The tour includes stops at hidden gems like New Suffolk’s Crushed Olive store for infused oils and vinegars, as well as exclusive vineyards that are not open to the general public.

What makes this tour stand out is its flexibility and intimate experience. The private vineyard visits can be tailored based on your preferences—discussions about boutique vineyards happen after booking, ensuring a personalized experience. The ride is relaxed, perfect for those who want to combine sightseeing, tasting, and some light exercise. Stops at Wickham’s Fruit Farm for local jams and honey add a farm-fresh touch, making this a well-rounded day.

Guests appreciate the knowledgeable guides and the opportunity to explore North Fork at a leisurely pace. At $199 per person, the value lies in the bespoke experience, the scenic views, and the opportunity to sample at a handful of carefully selected vineyards and farm stands.

Bottom Line: An active, customizable tour ideal for those who enjoy cycling and want insider access to boutique vineyards.

2. Full Day Private Long Island Wine Tours from New York City

This Full Day Private Long Island Wine Tour offers a comprehensive taste of the region’s best wineries and local attractions. With a dedicated guide, you’ll begin at the Bridge Lane Tasting Room, known for its award-winning wines and relaxed vibe, enjoying 4 tastings accompanied by music and outdoor games. Afterward, the tour visits Pindar Vineyards, the North Fork’s oldest and largest winery, where you sample 5 different wines.

What makes this experience special is its balance of wine tasting and exploration, with time to purchase bottles and enjoy the scenic surroundings. The focus is on quality and variety, with visits designed to showcase the region’s best, from small-batch vineyards to larger, established estates. The tour lasts about 8 hours, making it ideal for those seeking an immersive experience without feeling rushed.

Reviewers praise the driver and guide for being personable and knowledgeable, with comments like, “The wineries they chose were perfect!” At $189 per person, it’s a good value considering the curated itinerary and the inclusion of tastings at top vineyards.

Bottom Line: Perfect for visitors who want a guided, full-day experience with a mix of historic and boutique wineries.

3. Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

This Long Island Wine Tour North Fork Sights, Bites & Flights is a crafted, full-day experience that combines vineyard visits with local attractions and culinary experiences. It’s designed by passionate locals who know the best spots—like a secret speakeasy in Jamesport and favorite bakery for breakfast or lunch. The itinerary includes stops at multiple vineyards, oyster farms, botanical gardens, and charming towns.

The guide’s insider knowledge shines here, providing a richer understanding of North Fork’s history and food culture. The tour typically lasts 7 to 8 hours and features stops for small plates, shopping, and historic walking tours of places like Greenport, along with visits to favorite wineries. It’s a curated experience designed for those interested in more than just wine—wanting to explore local food, arts, and history.

Rated highly by travelers, this tour is best suited for visitors who appreciate a deep, multi-sensory experience. It costs $559 per person, but the customized, all-in-one approach provides significant value for those wanting a comprehensive day out.

Bottom Line: An all-in-one tour for curious travelers who want to combine wine with local sights and stories.

4. Long Island Wine Tour North Fork Sights Bites Flights Half Day AM

This Half-Day North Fork Sights, Bites & Flights offers a condensed but rich experience, ideal for travelers with limited time. Over approximately 4 to 5 hours, your guide customizes the tour based on your interests, visiting wineries, oyster farms, and local shops.

Focus is on quality rather than quantity; stops include the charming Mattituck area, where you’ll enjoy tastings at select vineyards, and a tour of an oyster farm near New Suffolk. The experience continues with visits to local chocolatiers and artisanal shops, making it a perfect way to sample North Fork’s culinary delights in the morning.

Rated highly for its personalized approach, this tour is good for those wanting a focused, scenic snapshot without a full-day commitment. Costing $339 per person, it offers solid value, especially if you’re tight on time but still want a taste of North Fork’s wine and food scene.

Bottom Line: Short but sweet, ideal for travelers seeking a morning or early afternoon taste of North Fork.

5. Long Island Winery Tour

This budget-friendly Long Island Winery Tour is a flexible private option that costs only about $100 per person. It includes transportation and visits to well-known wineries like Osprey’s Dominion and Duck Walk Vineyard. You choose whether to include tastings—some wineries allow self-guided tastings or pre-arranged flights—making it adaptable to your preferences and budget.

While reviews are limited, the tour shines for those seeking a cost-effective way to explore multiple vineyards with the convenience of private transportation. The itinerary typically spans 4 to 6 hours, allowing enough time for tasting, browsing shops, and enjoying the countryside. The flexibility to pick wineries and the option to include live music or small plates make it versatile.

Those on a budget or with specific winery favorites will find this an attractive, customizable choice. The lack of fixed schedules means you can tailor your experience, making it suitable for small groups or special celebrations like birthdays.

Bottom Line: A flexible, budget-conscious tour for visitors wanting to pick their own wineries and enjoy privacy.

6. Half-Day Private Long Island Wine Tour Experience

This Half-Day Private Wine Tour is designed for travelers who want a personalized experience without committing a full day. Starting from your hotel, you’ll be driven in a private vehicle to visit two key vineyards—Osprey’s Dominion and Duck Walk—along with some local stops, like artisanal shops or a quick wine tasting.

While it’s the newest addition with no reviews yet, the tour’s focus on private transportation and curated visits makes it appealing to those seeking flexibility. The 5-hour duration makes it perfect for a relaxed morning or afternoon outing, giving you enough time to enjoy the scenery, sample wines, and explore at your own pace.

Ideal for visitors with limited time or those who prefer a more tailored experience, this tour offers a quieter, more intimate way to enjoy the North Fork wine scene.

Bottom Line: A good option for travelers wanting a personalized, brief escape into Long Island’s wine country.

How to Choose Your Long Island Wine Tour

Selecting the right wine tour depends on your schedule, budget, and interests. For active travelers or those wanting a more personalized experience, the Private Guided Bike Tour offers a unique combo of exercise and exploration. If a full-day immersion appeals, the North Fork Sights, Bites & Flights Tour provides a comprehensive taste of the area’s food, wine, and sights.

Budget-conscious travelers may prefer the Long Island Winery Tour, which offers flexibility and private transport at a lower price point. Meanwhile, those with limited time should consider the Half-Day North Fork experience, perfect for a half-day escape.

Booking early is wise, especially in peak seasons from late spring to early fall, when these tours tend to fill up quickly.

Final Thoughts

Long Island provides a variety of ways to enjoy its wine country, whether you want a relaxed tasting, an active cycling adventure, or a full-day exploration of vineyards and local attractions. For a comprehensive experience, the North Fork Sights, Bites & Flights Full-Day stands out for its curated itinerary, while the Private Guided Bike Tour offers a more intimate, active approach.

Whether you’re celebrating a special occasion or simply seeking a local flavor, these tours provide authentic insights into Long Island’s wine traditions. Be sure to book early and choose a tour that best matches your interests and time constraints—Long Island’s vineyards are waiting to be discovered.