There are so many cities and I would say as far as the main ones (the big touristy ones), I haven’t been to one that I hated, maybe partly because I usually research extensively before traveling anywhere, so I don’t go to places that don’t meet the criteria I like, and when I do travel somewhere, I go to see sites that I am into (museums, historical places, nice parks, etc.). I’m into safe places, so I research the crime rate, etc., as well.
I live about an hour and a half by train from NYC, and i used to live closer, so NYC I’ve been to many, many times. It gets very packed around the holidays, but there’s nothing like it, really.
I used to live in a suburb of SF for a time when I was in elementary school, and have returned to SF several times as an adult, but the last time was when I was about 35. I loved it then but I heard there are a lot of homeless there now and I’m not planning to visit any time soon.
Philly, I’ve been to several times and it has some fun historical spots and a great zoo
Boston we go to a few times a year and it’s beautiful, fun, safe, historical, and only about two hours from where I live.
I’ve been to Orlando and Las Vegas and both were lots of fun but not really my vibe. Both were fun for brief visits, and memorable. I don’t really like crowds, and both were very crowded.
I heard Nashville and Memphis are both beautiful and fun, but have never been. A relative visited Oklahoma City and said it was beautiful.
A few years ago we went to Wisconsin, and liked it a lot.
I’ve been to Montreal, Quebec and Toronto. I really liked Quebec, although that was about 30 years ago.
Washington DC was great, and all of the Smithsonian museums are free (your tax dollars at work!). I found a great hotel in a great, safe location.
We went on a tour to Alaska and went to Fairbanks, Anchorage and a few other cities. I would say Anchorage and Fairbanks don’t have much. Palmer Alaska has a really great downtown area, kind of historic like straight out of the 1950’s, very walkable. Talkeetna and Denali are both great, but I think they’re towns and not cities.
I’ve been to Cody Wyoming which was great. A real “wild wild West” feeling. Also Helena Montana wasn’t too exciting but the Montana State Historical Society was there and I really like stuff like that.