Sailing North from Chesapeake - advice from Dad

Sailing into Baltimore Harbor can be pretty exciting for someone who has never done it, also Annapolis , ego ally, Chart House, Davis Pub equally exciting. But Annapolis should be fairly quiet during the week, no crowds except at lunch time at the market means there will be moorings available. A cruise up Spa Creek, under the bridge and up to the park covers a lot of waterfront as would Back Creek up beyond Jabins and around the corner That would cover two days and nights. I would not go further South, instead go North a third night in one of the creeks on the eastern shore and definitely a stop at the Chesapeake City Basin and the crab house that’s 4 nights transit the Canal and do the Delaware with a night at the Cohansey that’s 5 All pretty short runs with lots to see and a combo of motoring and sailing.. You could also do the Chester River up to Chestertown.. Depends on weather; winds & seas

You may want to pick just one city Annapolis/Baltimore. Get your paper charts out and look the area over.. Delaware City is a one day run from anywhere North of Annapolis assuming you will end up there to haul the boat ?

Think about wind direction, temperatures. Distance is not a problem unless you go South of Annapolis then you have to really watch wind direction which determine how easy it will be to get back up to the C&D Don't ignore the Delaware for a sail
"with the current" which can be pretty daunting on the ebb when you want to go back up to Delaware City time for the tide & current book East on the ebb , West on the flood back to C&D and Delaware City

Sails to nowhere are always the best, no time tables, just using the wind and tidal currents as in days of old