411 SW 3rd Ave, 228-5686
Not only is Huber's Portland's oldest restaurant, they also make a legendary Spanish Coffee. Spanish Coffees in general are a natural choice for the drizzly winter months, boasting a lovely marriage of coffee liquor and rum that work together to warm your soul. Widely regarded as Portland's best, Huber's Spanish Coffee is one you should actively seek out. Presented appropriately hot and crafted in an impressive flaming display of booze, glass, and fire, this $8 cocktail most definitely qualifies as perfect. (For a cold, frothy adaptation on the traditional coffee beverage, also try Holocene's [1001 SE Morrison] amazing Scorched Earth made with fresh espresso, Bailey's, crème de cacao, Kalhua, and 151, shaken and served up.)
816 & 820 N Russell, 460-0820
It's not the season for mojitos, but the 820 lounge's version, called the "O," is too good not to mention. Made with orange infused vodka, plus the traditional lime, mint, and soda, the O is like a beautiful explosion of citrusy freshness. The only drawback is that the O is so easy to suck down that you'll be on your third in a half hour or less. If you want to mix things up, other amazing drinks include the Tribeca, made with melon puree and Jim Beam, and the chocolate hazelnut martini, which is dense and rich and an ideal substitute for dessert.
1239 SW Broadway, 222-9070
When asked to pour their signature drink, the barkeep at Higgins replied, "We don't really have one. We're sort of old fashioned that way." To which I replied, "Sounds good. How 'bout a Knob Creek Old Fashioned?" The drink he then crafted for me sang like a choir of angels. Reminiscent of a time gone by, the seldom-requested Old Fashioned is essentially the proto-Manhattan, employing a muddled ensemble of bourbon, bitters, orange, cherry, and soda. When made correctly this masterpiece will quickly climb your "things to drink before I die" chart. At $6.50, this cocktail, served with Higgins' spectacular seasonal sweet chili hazelnuts, is easily the valedictorian of its class.
403 SW Stark, 525-0033
If you've never enjoyed the poetic combination of alcohol and cucumber, wait no longer. Thin slices of cucumber act like cool slivers of ice, and combine beautifully with the taste of lemon or lime. To discover exactly what I'm talking about, head down to Madame Butterfly and order up their cucumber margarita. Their recipe was invented in house, and combines Sauza Blanco tequila with triple sec, muddled limes, sugary simple syrup, and of course cucumbers, shaken and served on the rocks with a salted rim. Amazing.
4024 N Interstate, 287-5335
As dark as space itself and well within walking or Max-ing distance of your NoPo crib, the Alibi has the market cornered on one-drink vacations. Choose carefully, as you will become a staggering passenger to your own unfolding tiki-decorated destiny. My favorite, the classic Hurricane, is made with enough rum to cripple Jamaica and just enough orange and pineapple juice to facilitate easy drinkin'. Regardless, this tropical concoction will blow you away.