Begin at the Bookstore Bar, a small librarylike nook in the Alexis Hotel. It’s pretty empty early in the evening, which makes it the perfect place to grab a book off the wall or watch people hurry down First Avenue while you sip on your scotch. If it wasn’t for the bellhops outside, you’d never know it was a hotel bar.

Not even the Pike Street Hillclimb can take away from the appeal of Zig Zag big open booths are perfect for conversation fueled by their selection of impressively inventive cocktails. Even if you are drinking solo, the chatty waitresses will make you feel right at home.

Drink upstairs, dance (to pretty generic hip-hop) downstairs, and when you leave the Alibi Room you can marvel at the (let’s face it) disgusting gum wall just outside.

The bar at Il Bistro, just around the corner from the gum wall, is a cocktail landmark, and the happy hour—ravioli, shrimp in red sauce, calamari—is one of the best in town.

Stepping into White Horse Trading Co is like a trip to a small English town without the pesky plane ride. They only have a small selection of British ales, but drinking anything else while staring at a wall full of Anglophile kitsch wouldn’t be right. A word of warning: Avoid the bathroom; it doesn’t so much have a door as half a partition. Your modesty will thank you.

The Pink Door’s romantic candlelit atmosphere gets a little freaky late night—trapeze artists, dancers, and fortune tellers turn the classy joint into sexy alcohol-fueled circus.

NEXT: First Hill