As others have said, the sail to
Hawaii is a downwind sleigh ride. Not much of a challenge other than getting the most speed out of the boat if you are
racing. Easily done in 15-20 days without pushing the boat or crew.
The return is not so much fun as it's longer and often means Some windward
work sailing north to get around the high. It doesn't need to be hard on the
wind sailing however. In fact if you do point as high as possible you may very well end up sailing into the dead air in the center of the high and either be becalmed till they find your bones in the middle of the
North Pacific Garbage Patch or
power for days to get out of it.
If you crack off a bit to a close reach sailing will be way more comfortable, faster, drier and quite possibly have good winds all the way to your
west coast destination. It will still not be painless but relatively smooth sailing as the
wind clocks from East around to NE on the outskirts of the high.
Bad
weather can happen at any time of year but reltatively unlikely in the summer time.
The tankage of the Cat 30 is adequate for a
single person and the boat is more than capable of carrying provisions for over 30 days. A couple of
water filled gerry jugs along with a few with
diesel will greatly extend the possible time at sea or accomodate another person on board for the voyage.
I'm not paricularly fond of Catalina's build quality but they will survive most of the conditions that you would encounter on the sail to and from the Islands. Complete novices in unlikely
boats have done the circuit while experienced crews and well found boats have found the return sail more than they could handle. A lot of the abandonments seem to be from exhaustion after unexpectedly long bouts of bad weather and/or
equipment failure that could occur on any boat.
As neophytecruiser says, sail north out of the gate for a few days especially when the prevailing NE winds are honking and you'll get an idea if you and the boat are ready to follow the pineapple expressway return.