Portland, Oregon

Now that Portlandia is the hipster-indie-comedy hit of the decade, Portland jokes are pretty easy to come by. But the truth is, if Portland wasn't more or less awesome, it wouldn't be so easy to send up. This Pacific Northwest city sits at a confluence of rivers, and not on an ocean or lake, so it's a little bit of a break from the theme, but it's still got that nautical adventure vibe. With the perfect blend of outdoor ruggedness and urban style, Portland is the ideal getaway spot for people who are, well, cool. While there, be sure to imbibe both the locally brewed beer and locally cultivated wine.