Hi--we are a family of 4 with kids 9 and 10 and are thinking of doing a 2 week trip in Virginia for 2 weeks in August. We would be renting a place on chincoteague island for the 2nd week, in late august. we live in nyc and would be in search of an itinerary for the first week. We're interested in visiting colonial williamsburg/jamestown area for a couple of days but can't figure out what else makes sense as an itinerary for that first week that would hit some really fun places we and our kids would enjoy and that would not involve excessive driving. So I guess I have 2 questions--do we just head from colonial williamsburg to chincoteague via Norfolk or is there somewhere special stop on the way for a day or 2? And on the way to colonial williamsburg area from NYC what would be an itinerary that would be good--not DC as we have been there a couple times already. Viriginia is very confusing to me due to all the water ways and limitations on direct travel!
Family Itinerary NYC to Colonial Willamsburg
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You said you've done DC, have you done Philadelphia? Baltimore?
Another idea would be to pair your beach stay with a mountain stay. Wintergreen outside of Charlottesville, VA has a lot of activities for kids.
www.wintergreenresort.com
You could easily spend more than two days in Williamsburg. Your kids are at a great age to enjoy the Jamestown Settlement and Yorktown Victory Center.
http://www.historyisfun.org/
Add time at Busch Gardens and Water Country and you'll start filling a week.
http://www.watercountryusa.com/wc/
http://seaworldparks.com/en/buschgardens-williamsburg
Your kids would also enjoy the Virginia Living Museum, 1/2 hour outside of Williamsburg.
www.thevlm.org
Are you planning on returning to NY via the eastern shore route and the ferry?
Birdie has excellent suggestions, as always.
With a trip like that, pretty much the entire Mid-Atlantic is your oyster. If it were me, I'd head south down 95 to CW. If I were looking for somewhere to stop (and you don't need to, it's a pretty easy day's drive) I'd probably pick Richmond, which is an attractive city with a lot of history a Thomas Jefferson designed statehouse. Or you could spend a day or two in Philadelphia, which is roughly on your way, and full of interesting vaguely historical things to do with kids in the summer.
CW and environs can easily absorb 4 or 5 days, and you can get a combo ticket with the amusement parks. Assuming that Chincoteague is on your way back, eastern shore and the ferry is absolutely the best way to go. OC, Maryland can be a day trip from Chincoteague too, if you like. You could spend a night on the Jersey Shore on your way back too, if you liked.