Departure

$$ 130 H

525 SW Morrison St; 503-802-5370
If Pioneer Courthouse Square is Portland’s living room, Departure, at 15 stories high, is its exquisitely positioned penthouse. Sleek, intimate tables, couches, and a see-through railing frame an awe-inspiring view of the city. But don’t let the LA-chic scene fool you. Chef Gregory Gourdet’s Asian fusion cuisine is surprisingly unpretentious: from the pork belly (with pickled cherries and ginger) to wok-fired golden curry. With most dishes under $15, this could become your home away from home.

Radio Room

$$ 80 H ^

1101 NE Alberta St; 503-287-2346
Not only is the young crowd at this hipster hideout a good-looking bunch, but the view over artsy Alberta Street also guarantees some outlandish visual stimuli. Get there early to stake out your people-watching perch on the small rooftop or post up around the fire pit in the courtyard below. When it’s hot, cool down with something from the noir-themed cocktail menu before moving on to the meat-heavy main dishes.

Noble Rot Wine Bar

$$$ 17
1111 E Burnside St, Fourth Floor; 503-233-1999
Don’t spend another date night crammed into a “romantic” cubbyhole with candlelight singing your eyebrows. Noble Rot’s spectacular fourth-floor patio (OK, so technically not rooftop, but it is roofless) pairs innovative local cuisine and a thoughtful wine list with a breathtaking view of the downtown skyline—a trifecta that’s guaranteed to add a little amour to your evening.

On Deck Sports Bar

$ 136 H ^

910 NW 14th Ave; 503-227-7020
Despite the, erm, frat-tastic population this Pearl District hot spot attracts, On Deck’s bright, sprawling deck—the largest rooftop in Portland—is enough to keep you coming back. The food selection spans the narrow culinary spectrum between sliders and burgers, but they’re executed well and the drinks are all refreshing. Plus, with 26 televisions inside, you’ll never have to wonder about the latest soccer scores.

Laurelwood Public House & Brewery

$$ 42

5115 NE Sandy Blvd; 503-282-0622
Even stalwart Laurelwood fans can miss this hidden gem. Climb the stairs from the back parking lot to the rooftop, where cognoscenti enjoy a full bar, umbrellas, and the same selection of great beers and comfort food as downstairs. There are no views to speak of from up here, but when you’re staring down the business end of a pint of Workhorse IPA with sunlight on your face, who cares? —MP