Time your trip
Ross you have to time your trip to coincide with the tides. I've made the trip in two different boats, a 31' and my current 36', neither had/have any issues making headway on the bay. Yes you lose speed when against the tide but I've never encountered anyone sitting still as a result. If you time it right any speed you lose you'll more than make up when the tide turns. Don't forget you can run into nasty tides on the Chessy too. As far as anchoring to wait it out, just keep going. Slow is still better than zero.