Probably thinking this is unusual coming from a Cheasapeake guy, but we travel to the LI Sound every year as well as points north up to Marthas Vineyard.
Making a circumnavigation of Shelter Island or visiting some of the beautiful anchorages/ towns there was one of our suprise discoveries a few years ago, and no trip now is without a visit to at least two places there
As mentioned Deering harbor is a great anchorage for Greenport a neat little town with good basic seafood restaurants. Also the town marinia is redone and a good stop for a slip
We have found anchorages in Hogneck Bay as well as Cuthogoue Harbor ( Little Peconic Bay) beautifuyl as well as serene, biut can be hot on stifing summer days
West Neck Haebor near Dickerson Creek is a noice wooded anchorage with good protection and then their is Sag Harbor. A very expensive place to say, but worth spending a few days. tremendous restaurants.. One of the best provisioning stores ( Schivones) . We have takinen a slip (4 a foot) and anchored outside the harbor ( tons of traffic) I would recommend anchoring in Smith Cove ( about a 20 minute dinghy
ride ride for a great experience.
PM me if you want the names of some of the restyarants should you choose one or all of these places.