If any wine suffers from an identity crisis, it’s port. People have somehow gotten the idea that this rich, sweet fortified wine only keeps company with heavy desserts, cigars and boorish men in expensive ties. But port delivers complex tastes worthy of any curious palate—and most any occasion. And as its growing presence in restaurants and wine shops testifies, port is being rediscovered as a pleasure in itself.

Though it comes in a number of variations—the two primary ones being ruby and tawny—the signature wine of Portugal’s Douro Valley region is always the same at its core: a rich, full-bodied red wine to which neutral grape spirits (brandy) have been added during the fermenting process. The spirits arrest fermentation while the wine is still sweet and intensely fruity, boosting the alcohol level.

Ruby port, briefly fermented in barrels or steel tanks before bottling, retains strong fruit characteristics, smacking of jam and cherry cough drops (in a good way). Tawny port, by contrast, is aged at least six years in oak casks, causing it to lose much of its overt fruitiness and encouraging the development of more subtle flavors—as well as imparting the golden brown color for which it is named.

In the best years, when ripeness and flavor characteristics are particularly pronounced, port producers "declare" the vintage within two years of the harvest. The resulting wines are bottled unfiltered after a short stint in barrels, producing intense fruit flavors and tremendous tannins. (Ever steep your black tea for too long? That bitter flavor, which makes your mouth feel as if it is going to implode, is high tannin.) These tightly wound beasts need many years in the bottle to become the complex, integrated elixir that is vintage port.

While good port from a memorable vintage is not uncommon on wine lists, its price usually keeps mere mortals from tasting it. Portlanders are blessed with rare access to vintage port, however. Jim and Craig Plainfield, owners of Plainfield’s Mayur, have been buying port and Madeira (fortified wine from the island of the same name) since 1977, when they opened their upscale Indian restaurant—and everything on their list of fortified wines is available by the ounce. "When we started falling in love with port, you could buy the best vintages—1955, 1963—for nothing, $10 a bottle. And we did," says Craig Plainfield.

Elsewhere, it is virtually unheard-of to serve such a rarity as Plainfield’s 1958 Delaforce Vintage Port for $24 per ounce. What does this Dionysian delicacy taste like? Imagine a sour cherry enveloped in melted dark chocolate and infused with the burnt-sugar heat you taste in good bourbon.

Tawny port has an entirely different complexion. The most distinctive tawnies are usually a blend of barrels from different vintages. If the average age of the blend is 10 years, it’s legal to call the wine 10-year-old tawny—and so on for the 20-, 30- and 40-year-old appellations. Tawny ports develop sweeter, mellower flavors, slowly shedding the bright, red-fruit characteristics. Drier and lower-toned, tawny is like the sultry backup singer to vintage port’s lead guitar. Think roasted walnuts covered in caramel toffee.

Because they are ready to drink at release and need no additional aging, tawny ports are more approachable, both in style and price, than vintage ports. But if you want to really taste tawny port at its best—and its most challenging—try the older varieties, which push the tasting experience into unexpected zones where flavors of truffle and aged cheese reveal themselves.

Even the most extreme partisan of port would argue that the sweet wine’s rightful place is at the end of the meal. However, its trifecta of strength, sweetness and complexity makes it more than a great pair with dessert. Port is its own finale, a wine worthy of singular attention. So don’t worry about deciding between the cheesecake and the chocolate torte, the gulab jamun and the kheer. Just ask for the port list.