Smaller "Big" Cities

The cities you have listed are very popular cities in our country but at the same time those cities have so many choices, bait & switches that you just never know.. Say you were to visit a semi big city, yet still small enough that the variety is there but its not over loaded with options & different rates..
Take Milwaukee, my hometown for an example.. It's a big enough city to find activities such as art museums, water shows, rock climbing & beautiful site seeing. The providers that come along with a smaller city can actually be easier to find what your looking for. Everyone knows what they want & like, so doing a simple search could help your search vs. searching in a huge metro city & having many issues like, parking, donations for time (( every city has a different "going rate"))  
That being said, IMHO if I were newer to this & travel a lot, I would start with the smaller cities.  
I do hope your travels goes safely for you & I wish you happy hunting.

Be naughty & stay safe.

Xo  
Lynn Fairview

...so when I went to DC in May, I had a fantastic time!

I prefer going places that are easy to navigate and bike/public transit friendly. That's not everywhere..  

I had a great time in Cleveland (full disclosure: I'm originally from there). A lot has changed there since I left in 2005, and it was a welcome breath of fresh air.

I'm planning on Madison (which I've already been to and very much enjoy), and I'd like to explore Milwaukee and Minneapolis/St. Paul. I've got a list, so to speak.

Now, I don't know where I'd go as a hobbyist to seek nice providers.. Chicago, New York, Vegas, and LA are definitely full of ladies to choose from