Port is little known in the U.S., and those who do know it figure it to be sweet, sticky wine preferred by old ladies with cats or harrumphing English gentlemen.
Port, in fact, is wine -- legitimate, drink it like anything else wine. That we don't drink more of it in the States is a function of its price, for most port is expensive, and that we don't know nearly enough about it. (A concise port primer is here; for our purposes, it's enough to know that port is made like wine, but that fermentation is stopped to retain the sweetness and brandy is added to raise the alcohol level.)
The Sandeman (about $30, sample) is a good place to start to deal with both of those dilemmas. At $30, it's not as expensive as its big brother, the 20-year-old, which runs about $45. In addition, it offers classic port flavors like raisins and vanilla, with a wonderfully long pecan finish and a fine balance between the sweetness and its other characteristics. It's not sweet for sweet's sake, like a soft drink, but sweet in the way that a well-made dessert is.
Which makes sense, because port is first and foremost a dessert wine. There are suggested dessert pairings, including cheeses, but port is almost better on its own, served slighty chilled.