We’ve anchored in West Neck harbor under 15-20 knot clear conditions, near the beach at the southern end. Sand bottom very good (excellent?) holding. No surprises it’s just as you’d expect from the charts. We were the only boat there, there’s just beach and private homes, a small local marina at the north side.
If you like quiet this is outstanding. If you want shoreside action, just pull anchor head a mile or two south to Sag Harbor and there’s a summerstock theatre right by the dinghy dock, and everything else you need. Fantastic “old school Main Street” hardware store, supermarket, restaurants ranging from simple delis to gourmet and chic restaurants and shops frequented by the rich and famous, and wannabes of “The Hamptons”.
On the east side of Shelter I is Coecles Harbor — also quiet and beautiful, with one full service high quality marina. You can anchor on the south side, just inside the entrance to the Harbor. Or go further in to the marina. Watch the channel carefully because if you leave the channel you will go aground there. Also sandy bottom.
Dering Harbor is on the north side of Shelter island, it’s very crowded with moorings from shelter Island yacht club, which is a bit snooty in my humble opinion. It might be tough to find a place to anchor there.At the south end of the harbor is basic marina run out of the island’s only gas station accross the street. You can get a transient mooring from that marina or the club. There’s a nice little town there with a few nice restaurants and shops but you can walk the whole thing in about five minutes. Or you can walk to the nearby ferry as to Greenport which is a much larger town with more restaurants shopping supermarkets.