Lots of good advice already,
a couple other thoughts...
St Michaels is AWESOME, if you end up there during the week you could probably find enough room to anchor in front of the Inn at Perry Cabin, if you like crabs eat at the Crab Claw. You will be close to the Wye, if you can do it head up into Dividing Creek, trust me...its beautiful.
If you make the trek up to Baltimore you may be best served taking a slip at Harbor East, but if you want a free dock-age there is an area in Fells Point opposite the Broadway Parking garage, where the tugs dock, although no power or water, and it does get a bit crazy at night, but never felt not safe. The other option is the public dock at the Inner Harbor, where the Pride of Baltimore and the Clipper City dock. They have power and water and you're right downtown, again, I have never felt un safe...but?
If you head over to Rockhall area, definitely head up into Swan Creek, after you get through the inlet bear to port after the last green can, weekends can get crowded but a weeknight you should be fine with plenty of room and depth. Haven Harbor Marina is very nice, although I've never stayed so I'm not sure about cost but the facilities are fantastic. A trip into the town of Rockhall could be interesting, but not much going on, again, if you're fond of crabs Waterman's in Rockhall is worth it. They do have free dockage for patrons. We usually anchor in Swan Creek and dingy into Rockhall if we want crabs.
Annapolis, not going to add much more than what has been said except the moorings come with showers & laundry, and at night the rocking subsides. For me, its pretty spectacular to be downtown on the boat. You could try for a slip or the bulkhead off "ego alley" if you wanna show off the boat and don't mind spectator after spectator. Last time there it was 20 degrees and winds in the 40's (remember that gale last December 27 2009?)Burrrrr Oh yea, and Joss Sushi is just up the street
If you have never been up the Chester this would be a must! I would highly 2nd Grays Inn Creek and would add Langford Creek and/or the Corsica. Fun river to sail as well
So in summary, just a thought or two:
- HHS to St Mikes
- St Mikes to Wye (short day, gives time to explore the Wye if you have a dingy)
- Wye to Chester
- Chester to Rockhall/Swan Creek
- Swan/Rockhall to Baltimore
- Baltimore to Annapolis
- Annapolis to Rhode or West Rivers
- West/Rhode to HHS
PS. If you really wanna push one day skip something and head up to Worton or Still Pond. You can go "inside" Worton for more protection with good depth but gets crowded on weekends. Still Pond is wonderful, a family of Bald Eagles are in the area and much shoreline to explore...if you draw less than 5' you could try to get into Still Pond Creek, you will be hugging the shore after the inlet, which can have some current, but once inside you will be rewarded...I promise. (Shh, we don't like to tell to many about this spot
) If you choose not to go in with the big boat, check out the creek in the dink.