Well I live about 400 miles from my boat, and I have spent time in several locations over the years for vacation
cruising. From my location, several coastal cities in 5 states are within the 7 hour driving range. There are lots of options, and while you may not want to move every year, it is certainly doable. I'd identify a place to start, make it a base, with good transportation, reasonable dockage, all the resources you need for fitting out, and good crusing grounds.
Since you are talking summer cruising, farther north might be better and out of the storm tracks - well, for the most part.
The NC sounds and Chesapeake are pretty hard to beat. I'd find some places that have nice amenities for the kids
, like a pool. From experience, kids don't always like our idea of cruising. If you want your kids to keep joining you then make it fun for them. Not hard to do, and everyone gets what they want. One year I sailed up to the chesapeake offshore
and the family
drove up to meet me. We stayed on the boat and went to Busch gardens, the water
park, Colonial Williamsburg, ate ice cream etc, AND flapped around on a steamy, windless bay some too
Two weeks is not a lot of time to use your boat, but I get you want to dial it in before cruising. Pick a place to start, then research
your next destination
after the first year. If it is far enough south, you could get some good winter sailing in too. Sometimes we have very mild weather
, sometimes not, but usually changes every few days anyway. Just went cruising with my wife and one of the teens this week, and it was windy and cold. We had a blast anyway, just didn't cover a lot of miles. Didn't see any other boats out much.
Have fun, and keep in mind the several thousand dollars it will cost to own and maintain, even more if you won't have time to handle projects yourself. You can recon some locations while you're boat shopping