Head south on Main Street through our charming village of Southampton, founded in 1640. Continue south on South Main Street passing through the estate section. Be sure to spot the Halsey House and garden (built in 1683). Make a right on Gin Lane passing the iconic oceanside St Andrews Dune Church and continue to the intersection of Meadow Lane and First Neck Lane. You’ll see the all-grass tennis and croquet club in front of you. Either make a left and drive alongside the beach, or make a right to loop back toward Main Street.

From Sag Harbor, travel south on the Bridgehampton-Sag Harbor Turnpike until you reach the light at NY State Route 27. Continue south on Ocean Road for approximately 1 mile and make a left on Bridge Lane. Follow Bridge Lane until the end, passing the corn fields. Make a left on Sagg Main Street, pass the old cemetery on your left and make a right hand turn onto Gibson Lane. Enjoy the magnificent farmland leading you to the ocean.

Take NY State Route 27 all the way east, passing through Wainscott, the posh village of East Hampton, and Amagansett until you reach the beach town of Montauk. Be sure to visit Ditch Plains Beach and the Montauk Lighthouse.