I have sailed on and through LIS for 21 yrs. There are some "interesting" places to see and anchor
I would say that it is now the Land of NO. Most things you want to do you CAN'T or you have to pay someone to do it... Some places... Like in Fisher's Island charge for water
... and many places will not let you take on water
unless you spend on fuel
. Transient moorings are quite expensive and anchoring
areas are far off the landing.. so you'll have a long row or need a good motor
. Some areas now have no anchoring
at all and you MUST use a mooring
. I believe Huntington Harbor is one place. But you can anchor
in the prettier Northport. Many places won't take your rubbish and some you need to pay for it!
LIS is very very crowded with pleasure and working boats... and you will note that stink pots love to give you a wake and will always speed up and cross your bow at every opportunity.
The CT shore is more difficult to enter with lots of light pollution, shoals, ledges and rocks, but with chartplotters this is no problem. LI shore's harbors are pretty easy to make.
The latest craze out east is the cigarrette boats which make so much noise
you hear them long before and after they shoot by. The only thing good about them is they don't leave much of a wake, but they are more disturbing than all the PWC
which seem to be everywhere making noise
LIS is not Maine
. But there are some lovely spots.