Best known for celebrity sightings and posh stores, the east end of Long Island's South Fork is a surprisingly family-friendly destination with lots of perks for parents. Younger kids will love the area's focus on marine life, boats, and ice cream. Art, surf culture, and shopping will lure in the older kids. The biggest reason to come, however, is the incredibly soft and beautiful beaches. Everything else is icing on the cake.
The crowds descend on the Hamptons and Montauk from Memorial Day to Labor Day, with the peak season running mid-June to the end of August (the ocean water reaches its average peak of 70 degrees from mid-July to the end of August). Pumpkin-pickers and wine enthusiasts visit until the end of October, and then the town is more or less returned to its year-round residents. The advantage of enduring heavy traffic and peak season hotel rates along Route 27, the South Fork's main thoroughfare, is that activities and attractions are open all week. The shoulder months of May, September, and October are less crowded, but many attractions have limited hours during this period.
The best weather for sunny beach fun and cool evening strolls: June to August (average low and high temperatures for these months are 59 and 79). September is also lovely, averaging 55 to 73 degrees. July is, on average, the driest month. Get more weather info.
The Hamptons and Montauk are accessible by car, train, plane, and bus from all points west. MacArthur Airport (ISP), in Islip, Long Island, is the closest airport (about a one-hour drive without traffic). From there, you can rent a car and drive east. From Manhattan (and JFK and LaGuardia airports), it's about a two-hour drive to the Hamptons without traffic. It can take up to four hours during the Hamptons summer "rush hour" (heading east on Friday and west on Sunday between 4 p.m. and 7 p.m.). From Manhattan, you can also catch the Long Island Railroad or a popular Hampton Jitney bus east.
It is imperative to rent a car, especially for reaching those permit-only beaches (although taxis are available). You can rent a car from national rental chains at JFK International, LaGuardia, and MacArthur Airport. Hertz has a location in East Hampton, or try local agencies Pam in East Hampton or A-Car Auto Rental in Montauk. Reserve early!