If you want to ever escape the wealth and shopping of the Hamptons, your best option is Shelter Island. It is just a ferry ride away of about 10minutes maximum from Sag Harbour (or you can go from the North fork of the a Hamptons) and you find yourself in a completely different area.
From my understanding the island prides itself from keeping away from the mega wealth of the Hamptons, with very little development in terms of shops- 1 supermarket, post office, library, school, garden centres and farmers shops- but no retail boutique stores and most tourist shops and restaurant closing over the winter period.
The area can really be summed up by this rode sign on Shelter Island
The houses range from small American style houses to modern homes hidden in between the trees. But most of the larger houses are vacant until the summer months. The population increases by 4 times from June to September.
But don’t get me wrong, this is a stunning island to visit. The harbours are full of boats for sailing and paddle boarding. The beaches are sandy and perfect to chill out on. And the number of people are limited to the ferries that cross each day. But the best thing is that without a car, bikes can be rented- just take into account that you may have to be super fit to get around by bike as everything is rather spread out.
Whilst on shelter island a must is to visit Mashomack nature reserve as well as drive down to Rams Head. The later is really to see the incredible houses!