Re: how much experience do I need
Welcome to Sailnet, Randsail. You'll probably get responses to your question ranging from "are you firkin crazy? There's no way a $15,000 boat would make that trip" to "no problemo, dude, just take it easy and watch the weather". The bottom line is whether or not you can do a trip like that depends on you, the boat you choose, how much time you spend learning about the boat, boat handling, navigation, provisioning and provisions management, weather, etc. before you head off on the voyage.
Odds are, based just on the question you have asked, you don't have enough experience to know what the hazards are that you will face or how to mitigate or address them when you meet up with them, and for $15,000 you need to be very careful in the boat you select to get one that is both a seaworthy design and is in good enough shape to make the trip.
Take some time to read through the archives on this site, as your question, or ones very similar to it, have been asked and answered a hundred times. There's is a lot of experience and wisdom you can tap into here.....just be patient and be ready to sort out for yopurself what makes sense and what doesn't.
And - there's no better way to learn than sactually ailing, so find a way to get on other people's boats and get some experience on the water. Hang out at a marina and ask people if they need crew, find a sailing club and join it, etc.
Sailing isn't rocket surgery, and it won't take long for you to learn the basics and figure out what you need for a boat and gear to make the trip you're talking about.
S/V Everlasting Moon
1981 Endeavour 32
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Be joyful though you have considered all the facts.
- Wendell Berry