The Deal: $5 beer, $6 wine, $7 martinis, $12 endless starters. The cocktails are well-crafted, albeit weak. Food options are hit-or miss. The Dungeness crab-white cheddar sandwich is divine, but the asparagus salad is a measly excuse for even a garnish. To be satisfied, you must order three of them for yourself.
The Digs: Granted, the Fairmont Olympic isn't the first place that comes to mind for happy hour--who wants to risk spilling a drink on imported Italian décor and plush carpeting? Plenty of rich people, apparently. Business travelers, newlyweds, socialites, and even their teacup Yorkies gather in the lobby for happy hour, making it the most entertaining source of eavesdropping in the city.
Fried calamari and popcorn shrimp with basil-sriracha sauce
The Verdict: Your level of shamelessness determines the success of this happy hour. If you can ask for three orders of sliders, two asparagus salads, some calamari and popcorn shrimp, plus a martini for yourself without batting an eye, you will make out like a bandit. If acting this way in such a swanky atmosphere embarrasses you, save your $12 and simply order a martini and nibble on potato chips - they're free and come in a pretty silver bowl.