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The downtown Oakland bar boasts an array of fresh and unique cocktails. Its namesake beverage, the Penelope, is made from a mix of tequila, fresh beets, apples, pear, and lime.

Hold a glass up high as Skip Henderson and Starboard Watch, a pirate band, belts out old sea shanties. It’s just your average Thursday night at Quinn’s. The lighthouse dates back to 1890. The deck seats eighty, and the pub on the second floor has eight beers on tap and more than fifty bottled beers to choose from. The atmosphere is casual — patrons are permitted to toss peanut shells on the floor. The restaurant downstairs is more formal, but guests can order off the full menu wherever they are.

This well-ventilated and red-lit bar features lots of glamour mirrors, Japanese lanterns, and vintage mannequins. Eclectic nightly DJs spin golden oldies, hip-hop, new wave, swing, electronica, punk, metal, and just about anything else.

Once a favorite hangout for Oaktown pimps of the Fillmore Slim variety — according to urban legend, that is — the Ruby Room is a faux dive across the street from Lake Merritt where DJs spin a wall-to-wall soundtrack of punk, glam rock, and kitschy hip-hop classics. Characterized by its low ceilings, thick nicotine vapors, and scarlet glow, it’s one of the best places in Oakland to chat up sassy indie kids while drinking stiff, cheap drinks like whiskey sours.

Sex shop featuring lingerie, toys, and videos, plus a theater.

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