Re: 2019 Sailing Season on the Chesapeake
Highly recommend April vs March. Good probability of 60deg days and fair weather, even early April. March on the Bay is pretty ugly; it really does become an entirely different body of water across the span of just a week or 2. I did Deltaville-Annapolis the 1st weekend of April this year, and had a great delivery. If you can afford any flexibility, definitely bias towards April.
I've also done Colonial Beach-Annapolis- that's 2 days, so make it 3 for you? 5 seems excessive, weather notwithstanding.
My day 1 is 30nm CB to Pt Lookout or Jutland creek. Ride the ebb all the way down. Wouldn't bother with the time to go up to St Mary's, esp if just for a sleepstop. You're coming from ~Alexandria so add a day, play the current both days otherwise you have no choice but to fight it for at least part.
Day 2 65nm Pt Lookout-Annapolis. Underway before sunrise, arrive at sunset. Peeling off at Deale shortens that by almost 4H, so you can arrive for early cocktails. Stopping at Solomons only makes sense if you have to hit your destination mid-day vs late afternoon.