LI Wine Guide

Getting around

There is no train that stops at a tasting room and no bus that connects them. Every good Long Island wine trip is really a transportation plan with wine in it, so it is worth deciding how you will move before you decide where you will taste.

Getting out east

Driving from New York City is roughly two hours to Riverhead without traffic, and considerably more on summer Friday afternoons and autumn weekends. The Long Island Expressway to Exit 73 is the standard route; leaving before mid-morning or after the evening peak saves real time.

The LIRR runs to Riverhead, Mattituck, Southold and Greenport on the North Fork, and to Bridgehampton, Southampton and Montauk on the South Fork. Service is sparse compared with the commuter branches, so build the day around the timetable rather than the reverse.

The Hampton Jitney and seasonal coaches are comfortable and drop you closer to the walkable village centres than the train does on the South Fork.

Ferries matter more here than anywhere else in the region. Two short crossings via Shelter Island link the North and South Forks, and Cross Sound Ferry connects Orient Point to New London for visitors coming from New England.

Moving between tasting rooms

Once you are east, the practical choices are your own car with a designated driver, a hired car or private driver for the day, a seasonal shuttle loop, taxis and ride-hail — which exist but thin out noticeably in the evenings and in winter — or a bike on quiet weekday roads. Ride-hail availability is the thing visitors most often get wrong: a car that arrives in four minutes in Greenport at two in the afternoon may take thirty at nine in the evening in Cutchogue. If your plan depends on hailing a ride home after dinner, have a backup.

Car-free, done properly

Take the train or the Jitney east, stay somewhere walkable — Greenport, Sag Harbor, Southampton village — and hire a driver for the tasting hours only. It costs less than a full-day tour, keeps your own pace, and removes the drive home entirely. That combination is the single best answer for a couple visiting from the city without a car.

Timing notes

Autumn weekends are the busiest days of the year on the North Fork; treat Route 25 as slower than any map suggests. Winter thins out both restaurant hours and transport options, so confirm the return leg before you commit to the last tasting of the day.