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San Francisco: Espresso Milkshake at St. Francis Fountain
Chances are you're at the St. Francis Fountain for weekend brunch and you need a coffee, but looking around at the old-timey decor is making you crave a milkshake. Resolve this quandary by ordering the Espresso Shake ($5 small; $7 large).
The mixture of Mitchell's vanilla ice cream and a fresh shot of espresso made from Peerless beans boasts rich coffee flavor with just a hint of bitterness in the background. This isn't a treat for kids, and since they use real java, you still get your requisite hit of morning caffeine.
The candy-striped paper straws are a classic touch, though they don't always stand up to the slurping required to consume this medium-thick shake—ask for a few extra so you don't miss a beat when the first couple collapse.