Play: The greenest city with one of the best street food and beer scenes also happens to be the most dog-friendly. With 33 dog parks and more dog-friendly pubs and restaurants than anywhere in the world, Portland is a pup's paradise. Join locals in the meadows and woods at Thousand Acres Dog Park, dog paddle around Sauvie Island, or skip town for a day to hike the 9.6-mile Cape Lookout North trail along the coast.
Stay: Dogs stay for free at Hotel Monaco (from $185), which also offers complimentary bikes, nightly wine receptions, and a gluten-free bar on the hypoallergenic floor. Dogs receive food and water bowls, a dog bed, treats, and cleanup bags.
Eat: While you can assume just about every restaurant patio will welcome dogs, a few standout spots include Mother's Bistro (four minutes from Hotel Monaco), Lucky Labrador Brewing — order the Dog Day IPA — and Lardo, where the Pork Meatball Banh Mi with Dirty Fries will make you howl; it's that good.