4. Instead of the Hamptons, try Shelter Island
The summer playground of wealthy New Yorkers, The Hamptons swells in population in summer with both extended holidayers and daytrippers. The solution? Make like an in-the-know New Yorker and opt for Shelter Island instead. A five-minute ferry trip from nearby North Haven, Shelter Island has managed to sidestep the pretentious character, crowds, traffic and prices of the Hamptons (although locals have voiced their concerns about it turning that way — which is exactly why you should go soon). If you’re looking for a ‘sceney’ brunch filled with Instagram models you’re on the wrong island, but if you’re looking for a relaxed, lingering breakfast with ocean views, you’ll find it at local organic market and cafe Marie Eiffel Market. With only a couple of thousand people living there, it does come with a set of small-town challenges (there’s no hospital, for example, and if you get caught speeding, your name goes in the local paper) but for a taste of the quintessential life in upstate New York it doesn’t get any better — and you’ll save yourself a pretty penny too.