Originally Posted by emcentar
I do like the Cape Dory classic lines, would any of the smaller ones be better suited to the Chesapeake? I'm shopping in the 26'-30' range.
I like classic lines too, but that doesn't mean that boats with classic lines are necessarily the best boats for my uses.
Think about how you'll use it and pick boats that excel in those conditions, not in how they look.
In my case I care about sailing performance in light winds and do coastal sailing -- scenarios that a full keel boat doesn't do well in. I think my Pearson 28-2 is a little ugly (it's got a huge freeboard and is beamy), but the combination of interior layout and sailing performance make it one of the better choices for me.
If budget is a concern I'd also recommend looking at boats that are a little bit smaller. A 25-27' boat (often with an outboard) will have sails that are half as much as a 30' boat, a motor that is 1/4 as much (if it is an outboard), simpler systems, and be much less money to maintain. Moorage will be about $100 cheaper per month (at least here in Seattle). They are still good sizes for coastal cruising with a couple.