Great Cities - Not so visited

Some people recommended Oakland, California. As a Oaklander, I'd recommend staying in downtown Oakland at night as some areas can be dodgy. Everywhere else is OK in daytime.

I wonder if Point Reyes Station and National park has made it into the guidebooks yet. It is a bit north of SF and there are some wonderful hikes there.

Given my limited travel experience, I can definitely second a few of the suggestions on this list, as well as add a few of my own. Seeing as I am a Canuck I am a little biased to my own country first:

-Montreal and Quebec City are must sees
-Toronto (home city, again biased)....but to really experience the wide variety of cultures (most multicultural city in the world, so they say)you have to stay more than a few days
-Niagara on the lake
-Muskoka/Northern Ontario...one of my favourite places, though not a city

Of the cities in the U.S. Ive been to:
-Charleston, S.C-beautiful city
-St. Augustine, FL

Europe and beyond:
-Edinburgh-although pretty touristy I lived there for a few months and loved it....probably the most stunning city Ive been to
-Scottish Highlands-again not a city in particular but many ppl miss it on a trip to the UK and its probably the nicest part
-Brugge/Bruges, Belgium
-Bayeux, France-went for a dday tour and actually thought the town was very underrated
-Cadiz, Spain-someone mentioned it earlier and I totally agree...I didnt expect much other than a nice sunny place and wished I had stayed longer
-Essaouira, Morocco-great little surfing town on the coast
-Kusadasi/Selcuk, Turkey-beautiful area with tons of history, people were extremely friendly too
-Istanbul, Turkey
-Barcelona, Spain

Last two are very touristy but they are friggin cool cities so what can I say. Hopefully Ill add to my list eventually but for now thats all Ive got.