...She is a history buff (Hamilton got her hooked), so I was thinking maybe Boston or Philadelphia. My family hardly ever traveled growing up, so most trips are a first for me too. She is not the outdoors/nature type, but we all enjoy a good trolley ride or day at the science museum. DS11 has special needs and is a trooper about doing the intellectual stuff, so a good amusement park for him sometime during the trip is always appreciated.
Really looking to plan something a week long in summer 2021. Maybe two cities not too far apart, anywhere Southwest flies (companion passes!) Probably also a long-weekend winter trip to someplace snowy...
Funny, I was going to suggest Boston! You could maybe combine it with a NH vacation - a few days at each place. In Boston, you'd have the history and museums, and harbor/ocean, it's pretty much a walkable city with good public transportation, and in NH you'd have the mountains and lakes with a nice amusement park (Canobie Lake Park). Plenty of fresh seafood everywhere. A nice combination!
https://www.discovernewengland.org/
Me too - Boston sounds right up your family's alley! (We usually fly Southwest out of Providence, but I'm pretty sure they do Boston as well.)
And look into one of these:
https://www.citypass.com/boston
I would recommend the Science Museum and Aquarium, and if you like art, there is the MFA (which I love), Isabella Stewart Gardner Museum (a little more manageable size), or ICA (for more modern stuff).
The universities have some nice museums aw well - the glass models at the Harvard Museum of Natural History are amazing! And my son always liked the MIT Museum too.
There is tons of history, and don't forget the smaller places! Over the years, we've done the Freedom Trail, State House, Mapparium, and John F. Kennedy Museum, plus you can drive to Plimoth Plantation and out to Lexington and Concord if you'd like. The Adams Nat'l Historic site is also available in Quincy, which is accessible by "T" (MBTA - our not-always-underground subway) from Boston.
The nearest amusement parks are Canobie Lake (already mentioned), Six Flags (near Springfield - about 2 hours from Boston), and Lake Compounce (a smidge further, in CT, but with a really cool coaster built into the side of a mountain!)
I don't know if your kids are into zoos, but we have lots of those too. Franklin Park is excellent, and right in Boston. Roger Williams (in Providence) is wonderful, and Southwick's (in Mendon) is a hidden gem!
If I were to take a city vacation for history, I'd fly into either Philly or Boston, visit for a few days the take the Acela to the other, spend a few days and then fly home from there.
Good idea if you want to combine!