I came upon the following
on Yahoo Answers:
What's the cheapest sailboat that will get me from Oregon to
Noone really tried to answer the question and the answer period seems
to be over.
I'm not really going to answer it either, but I think similar thoughts. A couple years ago I read about Tania Aebi's voyage around the world and some wheels started turning. I lived in Kumamoto in 1992, so even though I am poor and cheap and have sailed exactly once, I spend some geek-time thinking about cruising to Japan.
Understand, then, that this answer is based on cheap research rather than experience.
The first thing to realize is that sailboats are designed for a variety of purposes. Some are blue water cruisers meant to live in and cross oceans. Most, however, are basically weekend party boats. The difference is in how rugged the materials and components are, and in design elements of the boat and its interior.
There are ways to beef up a weekend boat and make it more suitable for ocean travel and it is not uncommon to hear of people sailing to Hawaii from California that way. But you can also find horror stories of such boats falling apart piece by piece in bad weather.
When people live aboard their boat and travel from place to place it's called cruising. It became something of a fad in the 60s and 70s and there are a bunch of good books available used from that era. Those thirty year old boats are also still around and are now comparatively inexpensive. It is not uncommon to find Ericson 30s on Yachtworld for 10–15 thousand. Unfortunately they probably require another twenty thousand or more to bring them back up to a level of maintenance to withstand heavy storms.
Still, thirty thousand is not so different from ten. Certainly you don't need a million as one answerer replied.
It also seems to be true that cautious scheduling prevents a lot of problems. If you're in a hurry and make a beeline for your next destination then you leave yourself open to hitting bad weather. There seem to be ways of studying charts of weather patterns and timing your trip so you statistically avoid most of the dangers the ocean can throw at you.
Then there's the knowledge you require. You can take classes on sailboat handling, coastal and celestial navigation, anchoring, engine maintenance, etc. but they are expensive.
You also need money to buy food, water, and fuel for the trip, and not only how much you expect to use, but enough to cover the worst case.
If you're thinking long term, there may be a cheaper, and more organic approach. Learn to sail in a small boat like a sailing dinghy. Explore the local lakes and rivers. Move up to a larger but still small boat (18 feet, perhaps?) with an outboard motor and explore the coast, maybe do The Great Loop. Then you'll have much of the knowledge and experience to intelligently make the hop to a full size, off-shore capable boat and hit the Caribbean, Mexico, and then the vastness of the world. Knowledge and experience allow you to make do with simpler equipment.
There are lots of books by live-aboard cruisers. Some live expensively
but others live remarkably cheaply. Lin and Larry Pardey are probably the best
known. The have a number of books about their lifestyle in Seraffyn.
They have a chapter in
Seraffyn's Oriental Adventure
where they visit Tokyo Bay.
Also check out Annie Hill's
Voyaging on a Small Income.
Peter Aston self published a book called
Seto Summer where he and his
wife sailed to Kyushu from Australia.
Definitely check out
Sensible Cruising: The Thoreau Approach by Don
Casey and Lew Hackler. A beautiful book introducing the cruising
lifestyle and urging against the long what-if game I'm playing.
Upgrading Your Small Sailboat for Cruising by Paul and Marya Butler
shows how to address issues in a small sailboat to make it sturdier
and weather resistant.
There's a movie from the 60s called
Alone Across the Pacific
where Ken'ichi Horie sails a small boat from Japan to San Francisco.
It matches the original question quite well but in the opposite
direction. He wasn't especially well prepared but he made it.