Montauk is not a good sailor's destination
, IMHO. I've been there once by boat and would not go there again unless we needed a port for shelter or other reason. It is very sport-fishing oriented. We got a slip at Montauk Yacht Club which is supposed to be upscale but the rest rooms were dirty and service
was lacking. The docks were exposed to a chop from Lake Montauk and it was not peaceful. It's all about sport fishing
You can anchor
in Lake Montauk but dinghy
access is limited. If we ever go back we would be more comfortable at anchor, rather than over-paying for mediocre facilities.
Better destinations in that area are Three Mile Harbor (very quiet, but there are restaurants at some marinas), Orient Harbor (even quieter, no commercial
facilities), Shelter Island's 3 harbors, Greenport, and Sag Harbor. All of these are fairly quiet destinations except Greenport and Sag Harbor which are towns with a variety of shopping
As a sailor you will likely find great sailing conditions in Gardeners Bay and these harbors are each a few miles/hours from each other, making for nice day sails
as you hop between them. You could spend a week in that area and be very happy.