Thanks for all the input guys, I really appreciate it!
Sounds like 3 cities in 10 days is too much, if I had to pick 2 I'd probably go with London and Rome. I'm assuming that both places have some interesting world war museums/places of interests, could you recommend some? Same goes with Roman sights and medieval museums/sights/anything like that
As far as what I've enjoyed when traveling so far, I honestly haven't done much. Costa Rica once 20ish years ago with my Spanish language class, Hawaii 5ish times because that's where my wife is from. Vegas a bunch for poker, and Seattle a few times because I'm only 4 hours away. My favorite thing on any of those trips was probably Hawaii and seeing pearl harbor. Sitting on the beach isn't really my thing, but going to museums and seeing old boats or walking in an old submarine is FUN!!!!
My other big question would be "when" should we go? Our anniversary is August 25th, but we can travel whenever America's public school is out. I say that because we have a 4 year old, and our daughter is going to stay with grandma while we're gone and she's a public school teacher. So we were thinking about traveling the end of August because it's summer time for school so it works well for the grandparents, and that way we'd be in Europe on our actual wedding anniversary. However if that's a bad time of year, and say June or whenever is better to go, we'd rather choose a "good time to go" over the exact anniversary date.
Thanks again guys, really appreciating the feedback
(and don't hold back, I'm a travel n00b, so anything that sounds like a dumb idea, feel free to bash me
lol)