Where to Sail in NY
Yes sorry....you will need a taxi....and probably for most towns and marina''s. (Norwalk you might be able to walk to some??...there might be others?)
As for taxi''s in Stamford...they are lined up at the train station and easy to call. I have used them a number of times.
As for places to sail(and the original question)...I think Long Island Sound is one of the premier places to sail/cruise...much better and more places that the south side of LI. In the western part You have *wonderful* places to sail like Stamford, Greenwich, Oyster Bay, Huntington, Northport, Norwalk Islands, etc Milford, Bridgport, Pt. Jeff, Pt Washing. And they are all an easy sail with pretty and protected harbors. Sailing has been fine most of the past few years...Yeah...you will get those days (sometimes in august) when the wind is low in some parts of the day. Obviuosly Newport is windier, but its also many hours away from NYCity. But the relative location and protected harbours makes western LI sound great
The more east you go the more wind it seems you get....the places you can go are New Haven, Essex CT, The Conn River, Mystic, , Montuak, Block Island, Fisher Island The thimble islands, Orient Point, Shelet Island, etc.
ps...basically access to all these places are good...