RE: Rappahanock River vs York River I would recommend the Rappahanock as well, it's a much bigger river with more to see (Carter Creek, Corrotoman River, Urbanna), better options for eating, more marinas, etc.
I've been from West Point down the river to Glouster Point and back a few times on the York and it might be one of the most boring rivers I've been on in my life. There's really nothing there of interest (to me anyways) until you get to the mouth of the river.
Check out the Deltaville area for Marinas on the Rappahannock. Probably five or six big ones with drystack available. We usually launch at Norview, which is one of the nicer marinas. With a 23' boat, I will venture a guess that you'll want to get out in the bay to fish on occasion? If so, Tappahannock will be pretty far up river for that. If you do want to stay up in the rivers, the Tappahannock area is probably nicer for skiing and messing around with the kids.
It's worth your while to drive down to Deltaville and check it out, and when you're done there, shoot over and check out the north side of the Piankitank as well...also a neat river. We're also from Richmond and Deltaville is exactly 1.5 hours from driveway to ramp towing the boat...not too bad. Good luck!
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