De,
One of the reasons people are asking for more information is that without it, it's pretty much impossible to give good, specific advise. Based on my 35,000+nm of cruising, I know what I like, but I'm not you. What works best for you may be entirely different. I'm 60 years old and cruise double handed with my wife. We've taken our boats to the S. Pacific and back twice plus various other shorter cruises and deliveries.

Were I planning your trip, one of the first things would do is to pick up a copy of Jimmy Cornell's "World Cruising Routes" as an aid to planning your route. Just hugging the western S. American coast is going up wind and against the current the whole way.

As far as the boat goes, I like either a full keel or an almost full keel with a fully skeg hung rudder and the prop in an aperature like my Kelly Peterson 44. The hull should be a pure displacement, non-planing one and wind vane steering is a must unless you have a large crew. Note that wind vane steering generally does not work well on planing boats or fast cats.

I like cutter rigs with 3 reefs in the mainsail and a reef in the hanked on staysail. Others have reccommended a hank on jib, but I prefer a roller reefed one and use the reefed staysail instead of a storm jib. Without the ability to fly a reefed staysail, the ability to hank on a storm jib is a requirement in the high latitudes you are talking about. The big thing the roller reefed jib brings is that it removes the need to go to the pointy end of the boat in rough weather. My previous boat, was a Tayana 37 and I loved it, but I hated going all the way out to the end of the bowsprit to change jibs in bad weather. Holding on with one hand while I was plunged hip deep in green water and trying to change jibs with the other is something I hope never to do again. I do like the staysail to be hank on though. That way when you reef it, it brings the center of force down close to the deck, reducing the heeling force. Being in the center of the foredeck, it is possible to work far more safely than out on the bowsprit.

For someone else,. the complete opposite boat, like an Open 60, would be the ideal boat, but for you it's just impossible to say without more information.

Regards,
Dan Best