George the bay is one of the best sailing places in the US. You can find a great marina, you will want a genoa which you did not really use on SF Bay and a good light air chute. If you are going to race your boat then you need a full suit of light air sails. There is much better overnight/weekend cruising on the Chesapeake than on the SF bay. Very different sailing but still both are great.. and yes I have been on both. Depending on where you end up, let that drive where you look for a marina but there are very posh to very basic in the larger towns.