Rock Hall has grown so much ( as have many other quaint locations on the bay ) but still has a lot of charm.
As to the OP question, I think 8 hours is more than enough but it is weather
dependent. On memorial day weekend Saturday we sailed from the "R10" mark just South of the channel split to inside White Rocks at Rock creek in one hour. I'd think dock
if we were going to Canton would have totaled under 3 hours. We were averaging 7.4 knots that day with a broken block on our main. So I think that's a good estimate.
8 hours on a decent day will put you in St Michaels if the winds a favorable.
The trick is come some time July or August the "Maryland 3H Summer" will kick in and you motor
a lot. 3H is Hazy, Hot Humid.
We have a few more things to do but soon enough we will be going to the following great anchorages
Dobbins Island ( on the Magothy and gets CROWDED)
White Hall Bay - a little tricky but a 20 minute RIB
ride to Annapolis
and even less to the best crab place on the bay.