Travel guide
Long Island Weekend Guide: Beaches, Vineyards, and the Hamptons
A quick escape from NYC — how to balance beach time, wine tasting, and a little Hamptons glamour on Long Island.
6 min readUpdated August 16, 2026
Day 1: North Fork wine country
Head east early and spend the day tasting wines in Mattituck, Cutchogue, and Greenport. Stay in a vineyard guest house or a waterfront cottage.
Day 2: The Hamptons and the beach
- Breakfast in Sag Harbor
- Beach time at Main Beach in East Hampton or Coopers Beach in Southampton
- Lobster roll lunch in Montauk
- Sunset at Montauk Point Lighthouse
Day 3: Fire Island or a lazy morning
Catch the ferry to Fire Island for a car-free beach morning, or enjoy a slow breakfast and a stroll through a harbor town before the drive back.
Planning a Long Island stay?
Read the full Long Island destination guide — neighborhoods, seasons, and booking tips — then browse example rentals.
