I agree with Ripple. On LI Sound, you can run nearly year round or indeed year round. With one of our previous boats, we did run year round on the Sound for many years. The off season was some of the nicest times as there were no crowds! (LOL!) You do need to be self sufficient and extremely cognizant of safety issues. We always use Mustang Suits. Once we finish rebuilding and modifying the C-Dory, we will trailer it but one of the reasons for that is to be able to use the boat in the winter on nice days. Around here, it is either blowing like stink or flat calm. We simply skip the stinky days. We will be adding a Wallas for heat. Further north, you might have more issues with freezing, especially if you are in an area that is brackish which will freeze a lot easier than full salt water that frezes at slightly below 30 degrees. Even if you do not extend your seasons massively, you will certainly get more than 6 months of boating. Just be careful as April and early May, when the days are warm are times when a lot of people get into serious trouble as the water takes a long time to warm up and can easily be fatal if you go overboard.