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Do you have experience in extreme weather, going to Asia you'll probably encounter 50 foot high waves, super rough seas, have enough food supplies, fresh water for emergencies. I'd do a lot of research and try to contact anyone that has already done what you want to do. You may want to google sea sailing for stories nabout the adventure.
There are sailboats that are designed for the open seas. You stick to those brands.
You'll need a larger boat for long journeys. It's no longer possible to live on fish that you catch. You'll catch a lot of mackerel (yuck) and the seas are pretty much fished out by the huge factory fishing ships. You'll need space to carry supplies.
Docking fees are enormous. It is going to take a lot of a cash to arrive in port and tie your boat up for the night.
Yes, you sleep and put the boat onto an autopilot navigation system.
There are pirates off the coast in some of the oriental countries, and also in some places in the Caribbean. You are not allowed to have a gun on board when you arrive in some of those countries, so self defense is an important issue to get worked out before you leave.
You need much in the way of knowledge and wisdom when it comes to undertaking such a dream as mother nature can quickly take care of the unprepared novice out on the open sea,
Start by joining a local sailing school and learn the basics,perhaps buying a small sailboat like this http://4.bp.blogspot.com/--VVQbmiF1E...S9+17.6.13.jpg
As your knowledge progresses you can up the level of boat till you are competent enough to take on the challenge of long distance open ocean sailing on a sail boat of 40-50ft.
With good nautical schooling and much dedication you may be in a position to undertake your dream in 5 years.
I suggest that you look for others that do it, and offer to pay them so you can accompany them on a sailing. You would learn valuable experience from them.
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