3. CITIES 4 - 2

4. Anchorage, AK
1 - 1.29

Alaska's largest city is perfect for people who are not only a little lucky in the cash department, but who also enjoy the outdoors a great deal. Hiking, biking, and fishing are favorites, but in Anchorage you can also dogsled, canoe, pan for gold, ski, take a hot air balloon ride, or try your skill at snowmobiling.

Note: Anchorage is not for the easily chilled. We're not kidding; the threat of frozen hands, toes and tushes doesn't stop people from taking the one-hour trek to Alaska's top attraction, the Portage Glacier, where the "coolest" (get it?) take "iceberg safaris." From Anchorage you can get to six other nearby glaciers for hiking, viewing, boating, ooooohing, and aaaaahhhhhing.

Why is it so expensive? Again, because it's tough to get the tons of modern conveniences and products that Anchoragites desire all the way up to that block of ice.

3. Juneau, AK
1 - 1.33

Yes, another Alaskan town (and we refuse to explain again why stuff is expensive there). Alaska's capital city, now a "Naturalist's Paradise," is named for Joe Juneau, who found some gold in 1880 in the city's Quartz Gulch and Silverbow Basin - which led to a gold stampede when the good news spread. Back in the day, the gold mine in Juneau paid 2,000 men each $100 a month. In 63 years the Juneau Gold Belt produced close to $3 million in today's money in gold. Not too shabby.

2. Boston, MA
1 - 1.42

In Boston, you've got to pahk your cah neah the Hah-bah. But that's only if you have gas money left after you pay for everything else. Boston is, after all, 48% more expensive than most U.S. cities... and its professional's salaries don't make up the difference.

A real college town, a real trendy town, and a real laid-back town, the Bean Town is also a real expensive town. Those who can afford to do so hang their hats in the posh brownstones tucked beside Newberry Street's outdoor restaurants and trendy boutiques. But while apartments may be less costly in other areas of the city, rents are still usually among the country's highest, with one-bedrooms often topping $1000 per month.

Still, Bostonians get to enjoy seeing friendly faces, chowing down on the city's famous clam chow-dah ($5) and baked beans, and living it up in a young, liberal, fun city packed with our country's richest history and most exciting new culture.