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There are many categories to choose from: vintage port, single quinta vintage port, late bottled vintage port, vintage character (a.k.a. vintage reserve), tawny port colheita, tawny port, ruby port, and there is even white port. Ports can run from nearly dry to very sweet.
Vintage ports and single quinta vintage ports require years of bottle aging; so, they will probably not be of interest to you. My 1994 vintage ports (a great year) will be ready for drinking somewhere between '08-'12. They are also expensive: the current top releases go for $50-$90/bottle. Mature vintage ports, that are ready for drinking, from the '80s and early '90s are hard to find at retail and are just as expensive if not more so. Single quinta vintage ports come about when not all of the vineyards rise to the quality level necessary to declare a general vintage year. They can be good values; but, still require bottle aging. Late bottled vintage (LBV on label) port is aged twice as long in cask before being bottled and is often ready for drinking on release. Vintage character/vintage reserve port is similar to LBV except it's a blend of multiple vintages. Prices are a fraction of that for vintage port and they can be a good introduction to the taste of vintage port. Quality levels; however, can vary widely. It's best to get informed recommendations. I haven't tried any lately.
Tawny ports are completely aged in cask before being bottled and are ready for drinking when you buy them. Tawnies are blended from ports of multiple vintages [excepting the scarce colheitas which are vintage dated tawnies]. They have a different character from vintage ports. Tawnies may be labeled with the number of years they've spent in cask before being bottled (e.g. 10 yo, 20 yo, 30 yo ... etc.). They become increasingly more expensive with longevity; though, more than 20 yo generally doesn't yield much more for the money. As for the tawnies I'm drinking, I have just one bottle left of Niepoort Tawny Port Colheita 1983 which is outstanding; but, just about impossible to find anymore (it was originally about $30/btl.). Fortunately, I found a tawny port that I like just as much; yet, it doesnt come from Portugal at all! It's Hardy's Tawny Port South Australia Whiskers Blake NV. It's a very sweet tawny, aged for about seven years in cask, with layers of flavors that unfold as it warms in the mouth. This stuff to me is like honey to a bear. It's readily available in my area and costs about $13/btl.
Ruby ports come from simple, fruity, and light wines without great concentration. This is the cheapest category. The French like them as an aperitif. I prefer standard wines to this category of port.
White ports are fermented towards dryness and intended to be an aperitif. They are often mixed with tonic water, ice, and a slice of lemon. I'll settle for a wine cooler.
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