Thanks for all of the great suggestions, guys! I've tried a few of the suggested Scotches but never the Highland Park 18. So I'm leaning towards that one since I'm already a big fan of the 12.
I don't think I've tried a single one of the cigars you guys have suggested and I'd like to try all of them. I was already considering a high-end Padron, since I've always been tempted by those. So, 1926 or 1964 if I go that route? Davidoff are tempting too.