We sail through the end of Sept for sure, it's the best month here. Everything is still open, there is enough activity to not feel abandon, but crazy crowds are gone. By Oct, sailing is hit or miss. With our cockpit enclosure, we can comfortably sail, but who wants to dinghy ashore in a 60 deg windy drizzle, for example? Many seasonal places are rolling up the carpets in Oct and it's just a bit of a buzz kill.
If we get out at all in Oct, it's usually just a day sail or we stay at anchor and cook dinner aboard. I will say its super peaceful, as most anchorages are empty, zero, nada. We haul around Nov 1, so by this weekend, we're beginning the winterization process. Sails and engine are always last. However, when the ice maker, fresh water and heat are decommissioned, I start questioning my commitment.
Truthfully, it's not so bad to take a small break. We spend four days aboard for six straight months and get fairly compulsive about leaving the dock, staying at anchor and not agreeing to other invitations all summer. We invite a lot of people to join us and they do! At that level, it gets exhausting. I also have several winter projects that just can't get done while we're so active in season. However, after about 6 to 8 weeks on the hard, I'm dying to get back in and still have several months to go.
Btw, if you buy seasonal insurance, meaning you have a required layup period, that most commonly starts on Nov 1 here. I negotiate to Dec 1. Dreaming.
. And they know it.