I have done the October Shelter Island to NYC run quite a few times in both good and bad weather. Usually takes 2 days with a stop in port Jefferson for the night. Most recently we did it the weekend before last , was glorious weather but no wind. We usually have to motor most of the way as the fall winds in the LI Sound are usually from the west. This past trip was in my friends Tartan 34 we ended up in City Island.one year, right after 9/11 we went to the Brooklyn Marina. Quit a trip with the Trade Center still smoking!