Some great comments and suggestions so far. I'll try to add a little. Our kids grew up cruising in the mid-Bay region. Lots of trips to places like Oxford, Cacaway, St Michaels, etc. A couple highlights from their memories:
and swimming over tot he sandbar off Dobbins Island. The island is privately owned, but the knee-deep sandbar on the north end is a great place for a frisbee game
- Rhode River between Big, High and Flat Islands. High Island is actually underwater but is a fun place to beach a dink at low tide.
- The museum at St Michaels is a great place to tie up so that the kids have run of the lawn after closing time. Lots of fun evenings laying on the grass next to the boat looking at the stars.
As far as other things to do to make it fun.
- let them navigate, choose places to go etc.
- a search for the best ice cream on the bay. Comparing and discussing relative merits of each ice cream shop. Especially if there are more than 1 in a town
- drag the dinghy with the kids in it. Gives them a break from the parents and vice versa. (life jackets on of course)
- live MOB
drills/swim calls during the day. Plan these carefully to stay safe.
- drag toys. We occasionally pulled the dink, a sailing dink, a force 5, ... More important to make it a great time than to make great time.
- pick a book to read aloud during the evenings.
- take a kite and fly it off the stern
- encourage the building of forts in the cabin
. Creativity can run really wild. I never knew that much line could be strung that many places
- turn the cockpit
into a wading pool by stopping up the scuppers and pouring buckets on the kids. beware scooping up a jellyfish! (don't ask...)
By the way, the kids were the source of most of those ideas. We just had to be flexible enough to consider them!