You can make it to VA Beach from Hamden in a long day on the road - as long as you take the fastest route and don't get jammed up trying to get around NYC and Philly. Take the Merritt Pkwy to 287, cross the Tappan Zee, then the Garden State Pkwy to the NJ Tpk. It's 435 miles, you will want to take US-13 down the Delmarva and across the bay bridge/tunnel. If you have an EZ-Pass, bring it.

I have eaten at the Duck Inn in VA Beach - it's a very good seafood restaurant.

VA Beach to Orlando is a bit of a stretch in 1 day even via fastest route. It's over 750 miles. You might want to think about breaking that up, maybe get off the beaten path a bit.

A good rule of thumb is at least $100 per person per day.