Cigars and a glass of tawny is one of my favorite combos. The Taylor Fladgate and Grahams is what i usually have, although I haven't bought it forever. I really like it in the summer out on the deck. I usually go for the 10 year or longer. You can really taste the difference.
In any case I've had plenty of cheap port that was just as enjoyable, but i can't remember the names as i usually just buy what might be on sale at the time. Whatever you do, go Tawny, rather than red IMO. I really don't care for the reds..just too fruity. Tawny tends to be a dryer flavor.