A Philoshopical Question
A year ago, I went through about the same conundrum as you. I had a few years till retirement, and my ultimate goal was/is to "sail the world". But first, I would need to become a better sailor in (somewhat) protected waters before I could/should venture too far from shore. What vessel would be most appropriate under those circumstances?
After reading many posts on this and other sailing forums, our best course (pardon the pun) of action was to get a decent coastal cruiser with which we could learn to sail better and enjoy on the Chesapeake. If and when we take the plunge (oops, another pun) to go far from shore we would sell the coastal cruiser and buy a suitable offshore vessel.
Thusfar, we are enjoying the Bay in our Hunter 34''. It seems to be a very good boat for coastal cruising. We have much more to learn, so we''ll probably keep it for a couple of years. At some point we''ll decide if we still want to "sail the world" and if so, sell the Hunter 34'' and get something more seaworthy.
I hope our decision making process sheds some light on yours. In any event,
~ Happy sails to you ~ _/) ~