With preparation
I would say that both Hunters could do the trip, with the right modifications and preparations. The 37 is a much heavier boat, about 6000 lbs or so, I believe, and has a cutter rig and keel stepped mast. It also has a separate aft cabin, which could be handy if you have guests. Statistics also show that a bigger boat handles bigger conditions better. Of the Hunters of this generation, I have always felt that the 37 was the one intended to "go places". Having said that, I, myself, have extensively cruised my Hunter 33 over the past 19 years, mostly coastal stuff but some offshore and quite a bit of tough stuff.I am planning to head out into the Pacific next year, myself. BUT, I have modified it to make it more suitable for this use, and much more comfortable. It is a great boat for two people, and, arguably has the better offshore layout.....good sea berths, great head in the perfect location, good nav station, a spot in the companionway under a dodger that is almost like inside steering. The 37, due to its heavier displacement, will more easily carry a heavy load. Both boats are the objects of passionate affection by many of their owners, some of whom comment regularly on this site. In the "boats" section, you will find each model, extensively reviewed and critiqued and photographed.The Westsail 32 is a classic cruising boat, heavy as the dickens, but a better sailing boat than it is often given credit for being. It will go anywhere, and it will carry a bigger load, but it will probably not be anywhere the fun in the sailing department as the Hunters. And, unless you are ONLY going to be making passages, enjoyable sailing should count for something, in my opinion. There is a lot of daysailing involved in cruising. The Cape Dory is somewhere between the two types, and is generally well thought of, although I have no personal experience with it. No matter which boat you choose, get it surveyed rigorously, since any of these boats will have quite a bit of age on them. You may wind up spending a lot if basic systems, rig, sails, engine, etc. are past their useful life. And finally, the crew, its experience, endurance, capability, and compatibility will have a far greater influence on the outcome of your adventure than the choice of any of these four boats. John Cherubini II, the designer's highly knowledgeable son, often comments on this site. Hopefully, he will have something to say.Good Luck.