7. Vancouver, Canada
PRO: According to the locals, you can kayak and snowboard in the same day, since both outdoor activities are mere minutes from the city center.
CON: They spell it "city centre", no one actually does either of the aforementioned outdoor activities in the same day, and, well... it's Canada.
ALT: If you could fly directly to Whistler, we'd say Whistler. As it stands, you've actually got to fly into Vancouver to get to Whistler. Sorry.