Top 8 Long Island Wine Tours & Tastings + Self Guided Itineraries

Long Island Wine Country is home to a stunning wine region that is just a train ride away from New York City. Yet so many of us New Yorkers will fly across the globe for wine tours in Italy or Portugal, totally unaware that there are wine tours on Long Island! No flight or passport necessary.

Local Long Island companies offer a wide range of Long Island wine tours to choose from which include biking, farm stops, limos, and more. Some are designed for wine enthusiasts, while others combine sightseeing and culinary experiences. If you are interested in exploring the small towns on Long Island while stopping by Long Island vineyards, this Long Island wineries guide is for you.


The History of Long Island Wine Country

Long Island Wine Country is a wine region that began its history in 1973. A former 66-acre potato farm in Cutchogue transformed into Long Island’s first vineyard thanks to wine pioneers Alex and Louisa Hargrave. Soon after, winemakers, grape-growers, and investors jumped on the bandwagon — and the history of Long Island Wine Country had begun.

Long Island Wine Country is divided into three regions known as American Viticultural Areas (AVAs):

  • The North Fork AVA is home to most wineries in the region; it includes the peninsula from Riverhead to Orient Point, Robins, and Shelter Islands.
  • The Hamptons (aka South Fork) AVA is located on the South Fork of Long Island.
  • The Long Island AVA launched in 2001 as a domain for wineries that wanted to use blends from different parts of Long Island.

There are 57 distinct wine producers in the area of Long Island Wine Country. And the winemakers of this area are known for their “traditional meets innovative” wine-growing practices.


How to Get to the Long Island from NYC

If you’re coming from NYC, here’s how to get to Long Island. If you’re already in Long Island, feel free to skip ahead to the next section.

  • Bus: The Hampton Jitney is a bus service that departs from multiple locations in the City to small towns on Long Island (fares start from $37). Hampton Ambassador is a more luxurious bus option with complimentary snacks and WiFi (fares start from $58).
  • Train: The Long Island Rail Road (LIRR) departs from NYC’s Penn Station to most Long Island cities. Some routes require a train switch at Jamaica station and could get crowded during the rush hours. Online ticket prices start from $22.25.
  • Car: Long Island traffic could get heavy, but driving is still one of the most convenient ways to get to the area. Check if you want to rent a car in New York City and return to Long Island: few companies offer such service.

Long Island Wine Tours

There are many fun Long Island wine tours to choose from: family-oriented, bike wine tours, sustainable-centered tours, etc. We rounded up the most unique and trusted winery tours to explore in this region:

1. Long Island Winery Tour

Enjoy a full or half-day of wine and cider tastings with this guided tour. This company will pick you up from your hotel at your preferred time and guide you through some wineries including Osprey’s Dominion Vineyards and Duck Walk Vineyard.

  • Osprey’s Dominion Vineyards specialize in vinifera grapes grown on 90 acres. The vineyards are surrounded by the Lond Island Sounds and Peconic Bay, two most-beloved places for kayaking on Long Island.
  • Duck Walk Vineyards is one of the most famous family-owned vineyards and wineries in the area. Known for its spacious patio and variety of special events, it’s a winery you’d want to visit again and again as it always offers a different experience.

Why: Choose this private 5-hour wine tour for bachelorette parties so you can enjoy the winery scene with your friends at your own pace.

Book here: Click to check prices

2. Mattituck Guided Farm & Vineyard Bike Tour

If you love Long Island wine tours for their scenery, consider this non-traditional bike tour to local farms and wineries. On this adventure, you will be picked up from your hotel for a scenic bike ride through Mattituck. Here, historic buildings coexist with natural views of the Great Peconic Bay and the farms this area is known for.

Throughout this guided tour, you’ll have the opportunity to explore a handpicked selection of North Fork wineries. Stop by the beach, explore local farms along the way, and enjoy complimentary vinegar and olive oil tastings.

Don’t be shy if you are not a seasoned biker. As reported by travelers, a car will follow the tour in case of emergencies. You can hold your personal belongings, picnic blankets, and provisions there. 

Why: Chose this tour if you appreciate the beautiful scenery and are not afraid to break a sweat.

Book here: click to check prices.

3. Long Island Wine Tour from Manhattan

If you are not planning on spending an entire day or weekend in Long Island, consider this guided tour to Long Island wineries that starts from NYC. This round-trip adventure is perfect for larger groups who want to avoid driving. Professional drivers will take care of driving you from Manhattan to the North Fork of Long Island and back.

During this full-day trip, you will enjoy a fun day of exploring North Fork vineyards, a gourmet picnic lunch catered by Perfect Picnic, and 13 tastings at three famous Long Island wineries: Raphael Winery, Lenz Winery, and Osprey’s Dominion Vineyards.

Why: This tour is perfect for larger groups who want to return to New York City right after the trip. We love easy day trips from NYC!

Book here: Click to check prices.

4. The Hamptons and Long Island Wineries Private Tour

Always wanted to visit the Hamptons but never had a chance to do so? This 12-hour private tour is perfect if you get your crew together to explore this exclusive location. You’ll see so much!

First, you’ll head out east on a comfortable minivan from your accommodation in Manhattan. No train ride! No driving! You’ll start your journey from the town of Southampton, with its celebrity-filled restaurants, fashion boutiques, and beachfront mansions area known as a “Billionaire Lane.”

After enjoying a wine tasting in Southampton, move towards a former whaling city of Sag Harbor. There, have lunch at one of the harbor-viewing cafes and get ready to hit the Cross Sound Ferry to Orient in the North Fork of Long Island. Enjoy the farm stands and handpicked North Fork wineries. You’ll see three iconic parts of Suffolk, Long Island in one day! Amazing!

Why: Create a memorable experience for the team of your best friends on this private smaller group tour to the Hamptons + North Fork. 

Book here: Check the price for up to 6 people.

5. Mattituck Bike Wine Country and Fruit Orchard Tour

Enjoy a full day of fresh air and spectacular views with this biking and tasting tour around Mattituck. The length of the entire trip is about 13.5 miles at a comfortable pace. 

Throughout this North Fork wineries tour, you’ll make multiple stops to enjoy the area’s best local vineyards and wineries and indulge in decadent food pairings. One of the most exciting parts of this wine tour is visiting a fruit orchard. You can stretch and walk around or even pick your own fruit there.

A midday picnic lunch is also on the schedule. It’s a Mexican-style feast with homemade pies, jam, fruits, veggies, and signature cider. Enjoy a relaxing nap on your picnic blanket — because “wine not” — and head to The Crushed Olive for an oil-tasting experience.

Why: Get a variety of outdoor fun with this bike-centered North Fork wineries tour: wineries, oil tasting, fruit picking, and picnic.

Book here: Click to check prices.

6. Gold Star Limousine Winery Tour

If you are on a mission to find the most luxurious Long Island wine tours, renting a stretch limousine or even a Rolls Royce might be up your alley. Gold Star Limousine is a company specializing in private winery tours in Long Island that are so popular for special celebrations. 

Whether you are heading out “East” with a smaller group of friends for a bachelorette party or a big company for a birthday celebration, you’ll have the best time in your “party limo.”

One of the most convenient things about this tour is to include any wineries you want in your itinerary, whether on the South Fork or North Fork of Long Island.

Why: Plan your perfect wine experience with a luxury transportation service and a self-curated list of wineries to visit.

Book: prices upon request.

7. Long Island Winery Limo

In need of a romantic wine tour for two? Planning a family reunion on Long Island Winery Limo offers specialized tours to various regions and towns in New York City and Long Island. They will arrange such travel experiences for you. You just need to show up and have fun!

Some of the popular tours with this winery limo provider are affordable limo wine packages to Riverhead and bachelorette wine tours. The company’s fleet includes SUVs, stretch limousines, shuttle buses, and vans.

Why: Various limousine tours for different budgets.

Book: price depends on the wine tour packages you pick and the tour duration.

8. New Vine Wine Tours

Want to go wine and dine type of tour? New Vine Wine Tours specializes in experiences that combine wine tastings with meals at gourmet restaurants. Provide your pickup location, the number of people joining, preferred kind of vehicle, and the company will assist with picking wineries and breweries for your adventure.

Another unique offering by New Vine Wine Tours is personalized cakes, apparel, and drinkware. In other words, if you come up with the name for your trip, you can print it on your T-shirts, mugs, and hats. It’s an entertaining add-on if you are traveling with a larger group of friends.

Why: This tour is for those who prefer a tour with lovely little touches like personalized gifts for the group.

Book: price upon request.


3 Self-Guided Wine Tasting Long Island Wine Tour Itineraries

If you don’t see a tour that fits all your needs, here are some examples of self-guided wine tasting tours in Long Island that you can do yourself!

1. Northville + Mattituck Wine Tour (Self-Guided Itinerary)

Start your exploration of North Fork wineries by visiting family-owned Macari Vineyards. This mom-and-pop winery is famous for a unique private barrel cellar for parties of up to eight guests.

A must-visit during lunchtime is Rose Hill Vineyards, set on 28 acres of sustainably-grown vines. This chic winery features a historic 125-year-old barn and requires a reservation via Resy (limited to 90 minutes).

Finish the day at the sustainably farmed and family-owned Palmer Vineyards. Walk-ins are welcome but keep in mind that the place is usually packed for their Fresh Peconic Bay Oysters Weekend special.

2. The Hamptons’ Best Wineries (Self-Guided Itinerary)

There are three world-famous wineries to visit in the Hamptons: 

  • Wölffer Estate Vineyard is famous for its rose and cider with signature floral branding. This Sagaponack vineyard was founded in 1988 and is located on a gorgeous 55-acre territory.
  • Channing Daughters Winery is a chic winery in Bridgehampton that offers an artisanal selection of whites and reds.
  • Duck Walk Vineyard is based near a newly renovated Parrish Art Museum. The winery features a massive outdoor tasting room and a wide range of award-winning wines.

3. Cutchogue + Greenport Wineries Tour (Self-Guided Itinerary)

This area of Long Island is known for the Greenport wineries marked by resolute mom-and-pop charm. From the first vineyard in the area to the highest-ranked sustainable wineries, these North Fork wineries are the most fun to visit:

  • Kontokosta Winery is one of the rare waterfront wineries in Long Island. Enjoy the beautiful scenery of the Long Island Sound while sipping great wine from this family-operated vineyard.
  • One Woman Wines & Vineyards is a female-founded local business that emphasizes sustainable wine practices. Their wines are maintained with the highest standards recognized by the Long Island Sustainable Winegrowers Association.
  • Borghese Vineyard is a truly historical place to visit as it’s Long Island’s oldest vineyard established in 1973. Enjoy the award-winning blends from the pioneers of the wine industry or schedule a property tour with the winery owner himself.

How to Plan Your Own Long Island Wine Tour

Various travel companies will create your itinerary, assist with transportation, and recommend the best Long Island vineyards to visit. But if you don’t find something that aligns with your preferences, you can also plan the Long Island wine tour yourself. Here’s how.

  1. Google Maps is the best tool for planning new travel adventures. Pick the area you’d like to visit in Long Island (in North Fork or the Hamptons). Then zoom through the list of wineries on that region of the map and save via “pins” the wineries as “want to visit” places. Save that as a folder of “Long Island wineries” for the trip.
  2. Plan activities along the way. Typically, travelers visit at least three wineries in one day with a few recreational stops off the main road. For example, plan on spending an hour or so at one of the beaches in Montauk after a tasting at the famous Wölffer Estate Vineyard (in summer, they have live music every weekend). Or take a brewery tour at Montauk Brewing Company – this is one of our favorite things to do in Montauk!
  3. Hire a driver. Safety is everyone’s priority, and driving after a few glasses of wine is illegal. Hire a driver or pick a dedicated sober driver in your group.
  4. Walk-ins are welcome. You don’t need to schedule your wine tastings in advance: just walk in and pay for the tasting upon arrival. Be aware of the tasting room opening hours and the days select wineries are closed for private events.

Our Other Long Island Travel Guides


About the Author: Katya Bychova

Katya Bychkova is an avid traveler and writer based in New York City. Katya loves to spend her summers in the Hamptons and winters in the Caribbean while aiming to travel every month. Her travel adventures fuel her cravings for culture; warm-climate countries make perfect backgrounds for her Instagram. No matter where Katya goes, New York is the state that truly has her heart. She writes about beauty and lifestyle at the Style Sprinter blog.

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