I enjoy every city
Each one has a unique feeling.
-Bruma: I just love snow! I live in a hot country so I'd never seen snow, so Bruma is my dream. Cozy and warm houses made of wood... Aaaah, I want to live in Bruma :3
-Anvil: The whole Golden Coast is wonderful, the yellow blending with the blue of the sea and sky is beautiful and breath-taking. The castle, the harbor side, the ships, the lighthouse, love it!
-Chorrol: It has a nice feeling of a peaceful town, full of happy citizens. It feels bigger than any other city. I love stopping by The Oak and Crosier and have a good time.
-Skingrad: A mysterious city, with a different atmosphere. The big tall buildings, the secrets in the town, the count. It is a beautifully crafted town, the West Weald's red and green foliage spices up the place.
-Bravil: Depressing city, but that's not a bad thing. It is full of odd people and quests. It has an anarchist feeling.
-Leyawiin: I rarely explored Leyawiin in my playthroughs, maybe 'cus I hate swamps, but it doesn't mean I hate Leyawiin. It's kinda cool, but I wish I had explored it further.
-Kvatch: I loved battling through the scorched and destroyed city. It was very scary and epic. I wish we had the option to restore it (without mods).
-Cheydinhal: Weird, scary, dark and sad city to visit. It is a colorless and cold city. The Dark Brotherhood makes it even more creepy. I don't like the folk who lives there. But I like it for giving me this impression.
-Imperial City: Maybe the least I like, but it is still a great city. It could have been better though. It is massive, but most of it is empty. I really enjoyed walking through the Waterfront.