The North Fork of Long Island is New York’s premier wine region, with dozens of wineries along Route 25 and Route 48 between Riverhead and Orient. The region’s modern wine industry began in 1973, when Alex and Louisa Hargrave planted a vineyard in Cutchogue. It’s about two hours from Manhattan without traffic, and a chauffeured wine tour is the safest and most relaxing way to enjoy it — no designated driver, no parking, and a chauffeur who can keep the day on schedule.

At a glance
Distance from Midtown About 75–95 miles
Typical drive About 2 hours off-peak
Main roads Route 25 (Main Road) and Route 48 (Sound Avenue/North Road)
Famous grapes Merlot, Cabernet Franc, Chardonnay, Sauvignon Blanc
Best seasons Late spring to fall; harvest in September–October

Planning a winery day

  • Visit three or four wineries, not more — tastings take time.
  • Reserve ahead. Many wineries require reservations, especially on weekends.
  • Check group policies. Some wineries limit group sizes or don’t accept arrivals by limousine or party bus; a discreet SUV or Sprinter with a reservation is usually welcome.
  • Eat lunch at a farm stand, deli or restaurant in Greenport or Mattituck.

Beyond wine

  • Greenport: a maritime village with restaurants, shops and a vintage carousel.
  • Farm stands: fresh produce, pies and flowers.
  • Orient Point: quiet beaches and the ferry to New London, Connecticut.
  • Shelter Island: a short ferry ride from Greenport.

Why book a driver

Tasting wine and driving don’t mix. A chauffeur handles navigation, parking and timing, and a Sprinter keeps a group together. Read wine-tasting day tips for another option closer to home.

Book

See our hourly service and group transportation for wine tours.