If you are confined to two weeks, then forego the longer trips as that simply is just not enough time...hold that for later.
Phily, Hershey, Williamsburg could be one.
Another could be NYC and the Adirondacks and there are some nice parks in NY state (the facilities are a bit wanting though...old and crusty)...like Watkins Glen State Park, Letchworth (although that is pretty far west).
Key west...well some people really like it. I say spend two days tops there and spend the rest of the time in the Keys. Key West is rather a carnival like atmosphere IMHO.
Have fun!
Some places we would like to go to: Key West, Upper Michigan,
Upstate New York (Adirondacks), New York City (not a destination. maybe a day or two), Philadelphia area (not a destination, but wife wants to look around a day or so), Hershey PA (still not a destination), Williamsburg, DC, Colorado, Yellowstone...and more.
We could do a two week trip or two one week trips. I can't make any reservations anywhere until December, when I will be able to pick my vacation time for next year. Time would have to be either during the summer or one week of it during spring break.
Yellowstone would a stretch. It would have to be a 2 week trip and it would be the destination. That would give us a week of travel back and forth and about a week out there. Colorado would basically be the same thing, but more doable. All the others we could handle with a long week trip. 8-9 days. Any ideas or recommendations?