Is there a difference between boats for

[Greenhand]

There is no telling what kind of 5 year old boat will be available ten years from now. Something really wonderful might come about in boat design in the meantime.

Focus on sailing for now. Think about whether you will get to do that best by buying a smallish boat and sailing it near home frequently, or joining a sailing club, or chartering every chance you get.

Go to boat shows and make friends so that you see what is out there. Honestly, defaulting to Catalina and Hunter is kind of like taking the first hit of Google and thinking that is the definitive answer.

[gerson]

The ideal boat in today standarts shall be a Halberg Rassy or similar
Hallberg-Rassy - Sturdy construction, superb craftsmanship and signature seaworthiness
Those coastal cruisers as Hunters and Catalinas shall not be compared with true blue water vessels

[cwyckham]

You've obviously gathered by now that a Catalina or Hunter aren't the right boats for a high latitude adventure, though they can do just fine on the Coconut Milk Run.

Unlike others, I don't think it's silly to be thinking about the end game right now. It helps fire the dream to have a picture of the right boat on your desktop. Obsessing about the details right now helps keep you fired up, even if the details might change a bit in the next decade or two.

In my view, the Boreal 44 is a great boat for this mission. Also, John over at Attainable Adventure Cruising is designing a boat for exactly this that, if he can get it into production, will be a game changer. His site is amazing, especially for high latitude stuff, though you do have to pay for most content. At $20 a year, I've found it well worthwhile.

In the meantime, learn to sail, buy a small starter boat, and consider joining a racing crew.

[GrahamHO]

Also consider flying to Auckland New Zealand; about 15 hours flying time from Chicago. There are plenty of very good boats to look at here. At the the moment .65 cents US buys NZ$1. Quite a number of people sail here from the US and some sell their boats here and fly home. Lots of good cruising locally. Then you are positioned to sail back home via the Pacific if you want. You could round Cape Horn from here or back via Panama. I'm sure you can check out NZ yacht brokers from your armchair. You won't find all the US production yachts, I see referred to, here. The further south you go in NZ usually the more substantial the boats found though most are in Auckland and good ones too. Many of the worlds SuperYachts come here to be serviced as there is great deal of marine services available in Auckland and of course at .65 c = NZ$1. Also our seasons are opposite the north. I'm not sure about any import duty you might have to pay back in the US, though you could just sail the seven seas.