Simply put, what are your three favourite cities which you have visited? Why?
Washington, DC. It's a surprisingly chic, urbane, and multicultural city with tons of hidden eateries and a fantastic feel. It includes lots of priceless vistas and plenty of romantic nooks too. Nevermind the politicians and low skyline, I was taken with this city almost instantly. Lots of architectural character. You can have rowhouse, high-rise, or suburban living. Just over the river in Alexandria and Arlington, Virginia it felt just as tight and polished as in DC. Plenty of history here, too. Get a vista from above and much of the cityscape flirts with you, partially hidden behind mature trees. Plus the beach is not a terribly far drive away, nor is some sailing and a fantastic golf course in the Potomac.
Chicago, IL. Another very urbane city. Granted the Loop feels deserted after dark, this is still a bustling city with a great transit system and some really great neighborhoods (Wicker Park, Logan Square, Near North). It's a hub of architecture (Burnham + Root, Frank Lloyd Wright, among others), has tons of charming brick buildings and plenty of old-growth trees. Inner-ring suburbs take the most advantage of this. Grant Park, situated in the heart of the downtown waterfront, is attractively nesled between the built environment and the water, offering a relatively short trek to many of the city's attractions. I also love the city's gritty feel.
SF Bay Area, CA. OK, this is because it's home, where I was born and raised. The region itself was born of the gold rush, San Francisco quickly growing into one of the most dense cities in the nation. But it offers more than that. It was raised during the era of the suburb. Everything from urban to suburban living, to hilltop ranches are available in the area. It's surrounded by hills, so while the smog is bad during the summer, the vistas can be equally good, as are the driving roads. It may be arguably the most ethnically diverse metro area in the US, and there is no shortage of...just about anything you could want. Silicon Valley keeps it young and restless, meanwhile ToD's are popping up next to expanded and more integrated modes of public transit.