To be comfortable I would look for something with very low draft, two motors, and enough freeboard to take some 6 footers.
My boat is awesome at 3 foot or less - it rides like a cadillac. Unfortunately too much stress worrying about it getting worse.... which it invariably will at times.
I plan on buying a more seaworthy boat before I make more trips, not because mine can't do it, but because I really don't want to have to worry so much about the weather and etc.
Bluewater Yachts, maybe some sort of catamaran trawler, I'm looking and probably will be for the next five years before I settle on something.
Check this one out, it is diesel solar hybrid that can cruise at 6 knots on sunshine alone. It will cruise at 5 nm/gal at 15 knots when you use the diesel generators to drive its electric motors. No rudders and you drive with a joy stick......neat>
http://dsehybrid.com/dc9loser39157.5951967593