My in-laws have a time share in Williamsburg. We have been quite a few times but only twice with the kids. We spent one week there the summer before last and two weeks there this past summer. It is a fun place. We drove to VA beach the summer before last. We didn't have any issues finding parking, but we went during the week. I got to say the drive there was a pain (so much rush hour traffic) so you might want to leave later than we did. We did have to park in a paid lot across the street from the beach. I don't recall how much we paid for parking, but I don't think it was outrageous. My advice would be to go on a weekday after rush-hour. I think that helped us with the parking issue tremendously. I think it is possible to spend an entire day there if you like the beach. We only stayed about four hours. My in-laws were with us, including my DH's grandfather, who was 95 at the time. We also had our 2 year old daughter with us. While they had fun, they weren't interested in staying the entire day. We got there around 10:00 and left around 2:00.
I don't have any information about Yorktown Beach as we haven't ever been there.
I don't think you would really be able to do CW and Jamestown in the same day. There is too much to see and do at both places. In fact, I would recommend a few days at CW (if you have the time) and one day at Jamestown. We can do BG in one day. However, the last two years they have offered a pass that if you paid regular admission price for one day (no discounts), you could get in the rest of the summer (until Labor Day) for free. We did that the last two trips. DH and I took our oldest daughter once on each trip, and concentrated on the things she could do. Then we did a least one date night on each of our last two trips to ride the roller-coasters. The last trip, we did a few date nights because were there for two weeks. Another thing, you might consider at BG if you have little kids is the Elmo character lunch. MY DD loved that. The food wasn't that great, but the show was fantastic. She also really enjoyed playing in the splash areas at BG so make sure to build in time for that. Really, it depends on who fast you want to tour at BG. You could probably do it in one day if you needed to, but you could go at a much slower relaxing pace if you did two days.
Not sure about ice cream and pizza, but I agree with the above poster about Duck Doughnuts...we got them on our last trip for breakfast....so yummy. We did have ice cream at Coldstone, but that really isn't that special. We also really like the restaurant Food for Thought. It was wonderful. We also liked Bakers' Crust, which is also a restaurant. We always make sure to visit the Yankee Candle Store. My oldest daughter was just talking about that store last weekend. They have a few make your own candle type interactive experiences, a candy store, and a Christmas section, including Santa. It is way more than just your typical Yankee Candle store. We generally do dinner at a Tavern, which is expensive but fun. Water Country is also fun. My in-laws love the Cheese Shop, which is a little sandwich shop in CW. It is good but pricy.
Sometimes we will go over to the Williamsburg Winery. They have a nice little restaurant there, which we usually do for lunch (sandwiches and salads), but we haven't taken a tour there since our kids came along.
