Long Island

New York · LONG ISLAND

10 Long Island Tours That Pour Their Weight

Pick from these 10 and the day plans itself. Every entry carries its cost, its length and one plain reason to choose it.

Mattituck New York Guided Farm and Wine Country Bike Tour

Mattituck New York Guided Farm and Wine Country Bike Tour - Pedaling through Mattituck’s farm country

1.Mattituck New York Guided Farm and Wine Country Bike Tour

★★★★★★★★★★5.0 · from $139Our pick

Explore Mattituck by bike on a five-hour North Fork tour with wineries, a beach tasting, farm stands, refreshments, and free photos.

“Had a wonderful day biking with East End Bike Tours. Mike and Nicole were both outstanding! The bike ride was fun, the wineries both wonderful and the picnic lunch and olive oil tasting were outstanding. I would highly recommend doing a bike tour with them.”

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Mattituck Bike Wine Country and Fruit Orchard Tour

Mattituck Bike Wine Country and Fruit Orchard Tour - Riding toward Peconic Bay and The Crushed Olive

2.Mattituck Bike Wine Country and Fruit Orchard Tour

★★★★★★★★★★5.0 · from $141

Cycle 13.5 miles through Mattituck wine country, visit Peconic Bay, taste olive oil, shop farm stands, and enjoy support from a guide.

“This was a superbly organised tour with very qualified and competent guide tours. Safety was always paramount as was our comfort. The buffet lunch was amazingly tasty and included many vegetarian options. The rest was all super hRead more”

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Guided Farm and Wine Country Bike Tour in Mattituck NY

Guided Farm and Wine Country Bike Tour in Mattituck NY - Starting at 10:00 in Mattituck

Private Guided Wine Country Bike Tour in Mattituck

Private Guided Wine Country Bike Tour in Mattituck - New Suffolk and the Peconic Bay pause

Long Island Winery Tour

Long Island Winery Tour - Osprey’s Dominion: wine, lawn, and live music

5.Long Island Winery Tour

★★★★★★★★★★4.5 · 5 to 6 hours (approx.) · from $295

Review of Long Island Winery Tour with private pickup, tastings, live music, scenic vineyards, driver tips, pricing, and booking advice.

“Amazing journey. Anna our driver was a lot of fun and entertaining The wineries they chose were perfect! My sister had a great birthday celebration and we will definitely tell all our local friends”

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

Long Island Wine Tour North Fork Sights Bites Flights Half Day AM - Mattituck: start with wine, flowers, beaches, or bees

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

★★★★★★★★★★5.0 · 4 to 5 hours (approx.) · from $339

Explore Long Island’s North Fork with private pickup, oysters, wine, small plates, Greenport history, chocolates, and local stops.

“Working with Eric was seamless from start to finish. He’s professional, friendly, and truly looks out for his guests. Eric meticulously planned an incredible oyster farm tour where we learned the process firsthand and enjoyed the freshest farm-to-table oysters. It was the highlight that set the tone for a perfect day. He made my friend’s bachelorette weekend an absolute hit, made me look like a fabulous hero, and even helped capture great group photos throughout the day. As a passionate local and true North Fork insider, Eric curated the best of the region with beautiful wineries, hidden gems, local bites, and special surprises like Bobby Flay’s world-famous meatballs. From flowers…”

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Private Luxury Wine Tours of Long Island Pindar Winery

Private Luxury Wine Tours of Long Island Pindar Winery - Two hours at Pindar Vineyards

7.Private Luxury Wine Tours of Long Island Pindar Winery

★★★★★★★★★★5.0 · 6 to 7 hours (approx.) · from $180

Explore Long Island wine country on a private six-hour tour with Pindar, Raphael, Lenz, tastings, transport, and a careful driver.

“Our trip was absolutely refreshing and unforgettable. From the moment we set off, everything was perfectly organized smooth transport, warm hospitality, and a well-planned itinerary that balanced relaxation with adventure.”

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

Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day - Mattituck offers the widest choice

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

★★★★★★★★★★5.0 · 7 to 8 hours (approx.) · from $559

Spend a full day tasting North Fork wine, beer, oysters, chocolate, local bites, and Greenport history with private pickup and guide Eric.

“I don't have enough great things to say about this tour. From the first bite of homemade honey vanilla ice cream at the first farm stand through the stunning sunset with bubbly, we felt like princesses every moment of the day. On top of that, the tour itself was fascinating. Long Island has so much history and Eric puts a lot of work into ensuring he shares accurate, interesting information throughout the day. Ten out of ten stars. Highly recommend!”

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Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

Long Island Wine Tour North Fork Sights Bites Flights Half Day PM - New Suffolk pairs oysters with chocolate

9.Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

★★★★★★★★★★5.0 · 4 to 5 hours (approx.) · from $339

Explore Long Island’s North Fork with private pickup, wine, oysters, chocolate, small plates, Greenport history, and flexible stops.

“We absolutely loved the whole experience. The guide was knowledgeable, flexible and professional. We learned facts and history trivia that we couldn’t have known, and were able to go to place we couldn’t have thought of. We appreciated his good suggestions on stores and restaurants, which were very accurate as we found out later. Definitely recommend it to any friends.”

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Full Day Private Long Island Wine Tours from New York City

Full Day Private Long Island Wine Tours from New York City - Pindar Vineyards, five tastes and a bigger name

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

★★★★★★★★★★5.0 · 8 hours (approx.)

Escape New York City for a private Long Island wine day with tastings at Bridge Lane and Pindar, plus a dedicated chauffeur.

“A great experience, highly recommend! The sprinter van used was SO COOL on the inside, with Bluetooth hookup, AC, drink holders, etc. We had an absolute blast and enjoyed the ease of having our reservations made on our behalf. We LOVED our chauffeur, Mike-he was an absolute doll and so sweet! Great activity for our friends bachelorette”

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Long Island Wine Tours15Winery Visits & Tastings24Bike & Wine Tours6