trying to plan my off time

Anyone have the problem of deciding on whether to go on for two, maybe four more weeks but then it becomes a problem of what time frames fall into your off time? For instance, yes summer is great for on time but then there is the fall season and or Christmas. Of course you wanna look good for Christmas pictures and everything since your summer tan is gone and tank tops and shorts might be a little cold.
If I go for 3 months it will leave my off season through Christmas or actually just starting. Would you all just let it go for the full 3 months or maybe cut it back a few weeks so you can start earlier?
July Aug and Sept on then I will be off Oct Nov and Dec.
Not that big of a deal, I just wanna know other peoples opinions. Whether I am the only one who thinks about that or what? Maybe start my next cycle prematurely by two weeks??