Every time I read a thread like this I just envision my wallet opening up and dollar bills (or 20's, in reality) just flying out. I haven't had a port in ages, but when I smoked cigars I drank quite a bit. Port is a great pairing with many Nicaraguan cigars, which often have a nice, red wine character to them.
I recall Fonseca and Sandeman being the ones I drank most often (possibly because they were the ones I had easiest access too, it's been a long time so I can't be too sure).