Luxury holidays in Southold

Southold may sit just a short boat ride from its hot-shot southern neighbour, the Hamptons, but this humble – yet utterly charming – holidaying spot seems a world away. Flanked to the east by Greenport and to the west by Peconic, come summer this small town fills with weekenders unsheathing boats from their winter hibernation, city-escapers desperately seeking some beachside basking, and oenophiles touring family-run wineries. Things quiet down during the colder months, but Southold still has a warm cosy feel, as locals crowd ice-skating rinks and bring cheer with their annual WinterFest.
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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.

Getting there

  • 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.