not far...but
I wish I could be of more help, but since I suffer from the affliction of a very time demanding job, I don't get to go as far as I'd like.
The wife and I try to make at least two New London, CT to Block Island trips per season, and another two to Shelter Island. Of course there's a lot of daysailing thrown into the mix as well.
If I had the time, I'd like to venture North as far as Maine, or heading South, go for Florida and the Keys. I went to school in Maine and there's some absolutely gorgeous sailing country up there.
I have great confidence in the integrity of my boat, a 1979 H33. She may be old, but she holds her age well. Although the boat hasn't seen any real bluewater, the captain has (including charter and delivery work).