There is much discussion regarding pairing drinks with cigars. Here's my humble opinion on the subject; please note these are my personal views - the goal of this post is also to hear about your own favorite pairings.
Water - A must if nothing else. Helps cleanse the palate and keeps the mouth from getting too dry. My go-to beverage when I try a cigar for the first time.
Aged Rum - you haven't truly enjoyed a cigar until you've smoked one accompanied by some Zaya (drink it neat).
Other Booze - Sweet liqours like Bailey's and Kahlua work well. Dark liquors like whiskey, bourbon and cognac pair together as well. Light liquors and fruity liquors usually strike the palate wrong when accompanying a cigar.
Port - Tawnies yes. Rubies no. A good tawny has that oakiness and leathery rich body that pairs great with a stronger bodied cigar. My fave is Osborne's Tawny (cheap too!).
Coffee - Another great pairing. Any coffee goes good with a cigar, just be mindful to match the body of your coffee with that of your cigar. My fave has to be Larry's Beans (try the Mountain Sumatra).
Beer - Some folks like beer with cigars. I haven't found one that goes well with any cigar. Some like dark beer like porters and stouts as the richness and chocolatey-ness compliment the cigar flavor profile. But that's not the problem I have with beer and cigars, it's the hops. Hops have a bitterness/sourness to them that imparts those tastes onto the cigar. So a good cigar may taste sour when paired with beer.
Wine - My personal opinion is that wine does not pair with cigars. Period. Cigar Aficionado uses wine tasting cues to help describe flavors they get in cigars, but that is where the compatibility ends. Fruit and tobacco wreck the palate when combined for me.
Soda - This is a weird one. Regular cola soft drinks can be too sugary and distract from the flavors of the cigar. But for some strange reason, diet cola sodas work for me. Must be the aspartame. That said, folks have different reactions to aspartame, so this is just a recommendation based on my taste buds. Oh and of course fruity sodas like Mountain Dew and Sunkist don't work.
Apple Juice - this is a great palate cleanser. Seriously! Great for multiple smoke events.
What are your go-to pairings?