1) Portland, OR
-Mild winters (if you can handle the rain)
-Mild summers (warm, but no humidity!!).
-Great microbrews beer
-A nice city to look at (thanks to strict zoning and land use laws)
-Big but not too big. Traffic is a factor but is not insane (like in Seattle)
2) Toronto
-Probably the most multicultural city in North America besides NYC
-Lots to see and do
-Good public transportation
-Clean and low crime rate for a city that size
-Reasonable winters for Canada (thanks to Lake Ontario)
3) Vancouver, BC
-Beautiful scenary
-1.5 hours from Whistler
-Good climate (see Portland)
4) Miami Beach
-South Beach / Ocean Drive - need I say more?
-65F is considered cold
5) San Francisco
-Nice weather
-Great restaurants
-Golden Gate Park
-The Castro District.