I will disagree (as I've doen in the past) with Jeff's assessment of the suitability of the Dana for the Chesapeake. We sailed ours happily for years. We visited loads of places, sailed and anchored comfortably, with most of the amenities of much larger boats. I was never disappointed with its sailing ability -- and our immediate prior boat was pure racer (Melges 24). There are very few boats in that size range which could carry the payload we loaded in it and still sail so admirably.
That said, the Cape Dory 26 is a smaller boat in every respect except length over all. Like most of the models in the CD range, they are on the narrower side. And this model lacks an inboard diesel, which for many folks begins to mark the threshold between more capable/serious cruisers.
If you pursue the Cape Dory route, I would encourage you to bump up a bit and look at the CD 27 or 28s, with inboard diesel engines (even the later CD25D might be an option). These are closer to the Dana in size.
Going up a bit more, one of my favorite models in the line
-up is the CD30 Mark II, which was a bit of a departure in that it was designed by Clive Dent rather then Carl Alberg. It's proportionally beamier than its brethren and has a bit more modern appearance, with a very room interior for its size. Here's an example:
1988 Cape Dory 30 MKII Sail Boat For Sale - www.yachtworld.com