The family (wife and two kids - 4 and 5) and I plan to move our boat purchased last year from Tolchester down to Hampton (Southall Landing Marina). The boat draws 4'3" of water.
Here is our planned route:
1. Tolchester-Rock Hall
2. Rock Hall-Kent Narrows-Tilghman Island
3. Tighlman Island-Taylor's Island
4. Taylor's Island-Soloman's Island
5. Soloman's Island-Hoopersville (Honga River)
6. Hoopersville-Smith Island
7. Smith Island-Reedville
8. Reedville-Fishing Bay
9. Fishing Bay-Salt Ponds (Southall Landing)
Gosh your route looks perfect if all you want to do is move the boat. But if you want to experience some of the beauty of The Bay I would make some changes.
1st Day, Tolchester to Rock Hall seems like a very short trip. If you are looking to just get your feet wet then OK. If not and you can leave early in the day you could make Naptown.
2nd Day, Naptown to St Mikes. Kids will love it lots of history and fun place to visit. The only drawback if you will do a fair amount of back tracking when you leave.
3rd day, St Mikes to Taylors Island A nice long sail with not much room to play.
4th day, Taylors Island to Solomons Island. Also a nice place for any repairs you find you need (a major sailing center).
Your trip Solomons to Honga River seems to be a wasted day. You will be making little of no southing. I would think you could make Chrisfield.
5th day, Solomons to Chrisfield. Plenty to there and a good rest spot.
6th day, I like Smith Island but I would skip Smith and made it Chrisfield to Tangier. This place is like no other on earth! They speak a different language, well, a different version of our language. Enjoy yourself there...
7th day, Tangier to Deltaville. Another major boating center if you need repairs.
8th day, Deltaville to Mobjack Bay. Spend the night on anchor.
9th day, Mobjack Bay to home.
You need to plan in some lay days, days to stop and smell the roses, days to have some ashore fun.