Luxury holidays in Southold

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When to go

Long Island impresses year-round, but the summer has the most going on and its beaches are a welcome escape from New York City’s grind.

Planes
The closest international airports are LaGuardia and JFK (both in New York City), and Newark in New Jersey; all three are around a two-hour drive from Southold. If you’re flying domestically, Long Island MacArthur Airport is a shorter one-hour drive.
Trains
The Long Island Railroad runs from Penn Station in Manhattan all the way up to the edge of the North Fork, with stops in Southold and Greenport.
Automobiles
Once you’ve clambered out of NYC’s chaos, a set of wheels will serve you well in Southold, especially if you’re planning on cruising along the coast or hitting the Hamptons for a day-trip.