We sailed the Dory from California through Mexico, Central America, Panama, Jamaica, Cuba on down through the windward and leeward islands down to Venezuela and back up through all the Bahamas and into Florida and up the ICW for a ways. Then I ran out of money and had to go home. I found that we were able to do the entire three year trip with very little discomfort. There is the rub. What is discomfort then as apposed to what is discomfort now is quite a bit different. Comfort level is a moving target and it seems to move with age. The older I get, the more comfort I need. That doesn't mean a larger boat because then the labor to maintain and sail it starts to subtract from the overall equation. Every one will eventually reach a level that they will either live with or leave boating all together. I think I've reached my sweet spot so the 30 footer was great then and my 38 is great now.