Re: Cape Dory 30 - How slow is "slow?"
For the uses you describe the boat is a very good one. What you have in the CD is a good solid boat with nice lines and reasonable accommodations for what you propose.
Being slow also means being stable, and there is after all a reason they put motors on these things. The reason they call 'em slow is perhaps they are a tad bit under canvased - and safer that way.
The Chessie is noted for light air, you'll notice most of the folks that are actually going somewhere are motoring when the wind just doesn't cooperate. No big deal.
Lessons learned are opportunities earned.