Portland
View of downtown Portland
Danita Delimont—Getty Images/Gallo Images
The state of Oregon has a major perk for the penny-wise: there's no sales tax, which means that plaid flannel shirt will cost you a lot less than it does at home. Stay at the The Benson Hotel (about $151 a night), built in 1913 and still one of Portland’s grande dames. For a great view of the city, get to the happy hour early at Portland City Grill and nab a window-side seat; it’s on the 30th floor of one of the tallest buildings in town. Your order: $6.95 shrimp and grits; $5 garlic fries; and a $6 glass of white wine.