Becoming a whiskey snob just made me wish I could abide cigar smoking.

How do you get to sleep? I’ve tried tea at various times as a substitute for an evening alcoholic beverage but the caffeine hinders my sleep. I already drink too much coffee before 10am, so adding more caffeine later in the evening has been a problem when I’ve tried it.

Kukicha (though it still has some caffeine), hojicha, rooibos, various other tisanes. Though, the caffeine content of anything that isn't red tea / puerh doesn't effect me much, and there are a lot of good decaf options.

I would also assume multiple brewings will see caffeine levels drop off sharply.

I suffer from chronic insomnia, and I certainly didn't notice the afternoons and evenings spent on a pot of good oolong to be any worse than the same with herbal or rooibos.

There are some naturally caffeine free tisanes - I'd suggest rooibos or honeybush.