While a bit unorthodox for a yippie, the suits have it right on this one; Sailing is fun and a very revolutionary way to live and travel. Once a boat gets "old" the yuppies, being disgusting spendthrifts, have to upgrade so they aren't shown-up by the Jones'. Most yuppies run the sails for looks and are under power at all times. Save a dinosaur and use the motor only when you have to.
Buying and Preparation
A 27 foot ocean-capable craft can be acquired for very cheap by visiting the docks regularly and asking about any abandoned boats being sold to recover mooring fees. Look for auctions in the paper and inquire at boat repair shops. Always go browsing with an experienced skipper who can assess weak spots in the rigging and hull, sail quality, and engine wear before buying.
With a little cleanup you have a house, an intercontinental get away vehicle, and an almost free way to get up and down the coast. For free mooring, look for a small sound or cove near a public park where the water is in another jurisdiction, drop an old engine block with a chain and float, this is your new anchorage. Leave no valuables in your boat, the only security is that thieves must cross a bit of water. Never leave the launch aboard if you use this storage method and even more importantly do not leave your launch at the beach or thieves will have easy access to your sailboat and free launch. If the sailboat doesn't have a launch a canoe will work quite nicely, also it is easier to paddle than a Zodiac.
It is worthwhile to spend a few months getting familiar with your boating skills. A boat is not a car you are at the mercy of the wind, current, and inertia. A power motor is a good idea for docking. Accidents with boats can lead to a sinking or severe damage especially in a boatyard, some places will land you in jail if you damage another boat and are uninsured. Look into a university sailing team or post an offer to crew for free to locals out for a joy ride.
All of the advice in this article is great for a cheap abode and for the fun of it. However one should never enter into the world of sailing lightly. The old saying that I've heard is that "The Sea is like a woman; Know how to handle her and she will love you. Because if you don't know how to handle her, she will wreck you."
This is true and with this said it should be seriously recommended to anyone who is considering taking up the sailing/boating route that they enroll themselves in as many safe boating and seamanship courses as possible. Here you will gain much needed knowledge on how to handle the sea and it's challenges. Some of the best instruction in seamanship is offered by the U.S. Power Squadron and U.S. Coast Guard Auxiliary. All of their classes are approved by the Coast Guard for training purposes. One I'm sure would agree that it's better to never have to call the Coast Guard or any other law enforcement than to have to perhaps explain your stash on board. Therefore with this premise alone it's important to learn good seamanship and how to handle your boat. Also the classes offered by the USPS and USCGAUX are usually low cost and rarely over $100 each. Also other agencies such as your state's Bureau of Marine Resources may offer some boating classes for free. In addition to this one may find some classes online for free such as the one offered in basic boating skills by Boat U.S. which is on their website. Boating is not like car driving and there are numerous more rules that one should be aware of in order to safely operate a boat. Also one should consider investing in the Boater's Bible, also known by it's official name, The Chapman School of Seamanship Manual of Basic Seamanship. This book contains all that one needs to know for safe boating skills from things as simple as how to tie an anchor on to what international signal flags mean. It is an indispensable tool to boaters.
Look for ads of people who want a crew for an ocean crossing to Europe, South America, or Hawaii trip. Get to know those that want you for crew a little before agreeing to accompany them on such a trip. There are stories of the free riders being treated like slaves in exchange for their food while the yuppie owners sat around smoking (and not sharing) their doob.
The skipper is one of the top reasons to choose or reject a boat. If she is a philosopher queen the voyage may be hard but her leadership will keep arguments from going too far and working arrangements fair. The captain is the heart and the head of the boat, defy her at your own and the crews peril.
If you like math or are paranoid that the aliens are going to steal the GPS satellites, learn to use a sextant. A sextant, while sounding sexy, just measures the angle between the sun, moon star, or planet and the horizon. When combined with a stellar movement book and an exact clock you can compute your location on earth to within a few nautical miles.
If you have a stash hide it well, the US Coast Guard feels the right to patrol the high seas and search any vessel it wishes. Flying the pot leaf flag is a sure way to get boarded, try running the Jolly Rodger like American imperial aircraft carriers instead.
Stowing Away and Cargo Cruises
Old books mentioned cheap passage on cargo vessels. Our research seems to indicate that said travel is still slow, but can now cost as much as $3000 to get to Europe or Asia from the North American coast. You might investigate getting a job on a cargo ship, but few have American or Anglo crews, and some require you to have some form of merchant seaman registration. Stowing away on most modern vessels is not such a bright idea either. With most ships being either auto, container, or tanker there is a very small crew but this also means few places to hide with any shelter and nowhere to get food or water during the several week voyage. Some human smugglers pack a group of refugees into a shipping container with a toilet bucket, some water, and food; there was also a report of terrorists making hidden rooms in the rear of containers although this seems uncomfortable as well and still expensive.
The exception is cruise ships and ferries. Once you sneak on board, if you can look the part and nap in the lounges by the pool, you should be able to stay out of the brig. Eat only at open buffets or leftovers you find since there is assigned seating for meals and purchases are charged directly to your room account and there's no cash or credit card purchases. A real help is to meet a cool passenger and have them smuggle food and let you crash in their room. We once read of cruise ship stowaways who were fine until it was noticed by room service crew that someone was sleeping in the beds of a made up cabin that was as yet unassigned. Do not get off of the ship at port visits until you reach your destination. Ferries are probably the easiest ships to stow away on since the trip is usually less than a day or two and we have never been asked for a ticket once aboard.
It used to be European radio waves were full of pirate stations with great music and radical politics immune from prosecution because they were in international waters. Since the signing of international sea treaties a pirate operator transmitting on unauthorized signals may be boarded even in international waters and the craft impounded by the offended nations navy or coastal police. Tehcnically, one could get a broadcasting license from a country and register the ship there, but broadcasting into another country's territory from outside their national waters could cause an international incident.
International Maritime Law
The days when people could just go off into international waters and be immune to the laws of any country are pretty much gone. Those with spare time can study the following databases on the various laws of the sea:
- International Law of the Sea Research Guide 
- International Tribunal for the Law of the Sea 
- United Nations Convention on the Law of the Sea 
One may wish to consider is to build their own boat especially if cost is an issue or finding a seaworthy boat is an issue as it can sometimes be. There are numerous books out there on this. Some of the best are those by George Buehler such as Backyard Boat Building, Howard I. Chappelle such as BoatBuilding and the History of American Small Craft, and the Sharpie Book by Reul Parker. These books all illustrate step by step how one can build a boat. A sharpie is one of the easiest boats to build and will provide the added benefit of not only being a seaworthy craft but if made of wood will lend itself to simpler maintenance anywhere in the world but also due to the hull design allows one to go inland to many places many larger boats can't go. Which can be most helpful if needing to find a good hiding location from which to plan your next move or just to satisfy the need to get away from everyone and everything. Also based on my research a good cruising sized sharpie could be built for less than $1000. The only problem might be where to build but then seeing how a group of two or three could build them one in a matter of a couple of weeks I would say that any State or National Forest or State or National Park that lies on a gentle flowing river should provide a good location on which to build. Just remember to camouflage your boatyard so that Smokey (aka Forest or Park Ranger) doesn't come looking for you and practice good woodsmanship so as to not start any forest fires or brush fires which could ruin your boat and boatyard not to mention call much undue attention to you.
For undocumented low budget travel in the Caribbean, Hawaii, or other island chains it might be possible to make your trip using an outrigger canoe. The first outrigger canoes were paddle powered but of course a sail does the work for you. You can build a heavy slow moving burnout canoe from a log like the natives did, but why not find a regular canoe to give you a jump start. Your outrigger pontoon can be a shaped piece of sealed wood or fiberglass filled with expanding foam. You will most likely want to build the cross members from a good marine treated lumber, properly glue laminating and sealing several thin boards is stronger than a few thick ones. The best mast and sail is from a used windsurfing board, you will probably also want to make a jib sail. Be sure that the spacing of your outrigger is far enough to prevent swamping in high wind, for serious sailing a second outrigger might even be included on the other side but above the water line. You will need to build a strong rudder that will not break, many people put a trampoline like tarp on the cross members connecting the so they can sleep stretched out. you might consider filling empty spaces in the canoe with expanding foam for additional emergency flotation. Stress test the cross members occasionally so they wont fail when you are in high wind. Instead of an outrigger a second canoe can be used to build a catamaran. Don't forget high energy ready to eat food, water or a reverse osmosis fresh water making pump, communication, and navigation gear as well as your emergency signal and man-overboard equipment.
A quick note: do NOT attempt to cross from one island to another until you have reliable data on what, if any, currents there are in the waters you will be crossing. Getting swept away in a sailboat can be an inconvenience; getting swept away in a canoe could very well mean never being seen again.
Below you'll find a couple of links to websites offering cheap boats to be bought. These are both in Florida which on the East and Gulf Coasts is going to be the best place to look for a boat. If you're out west check out California. It seems that both LA and San Diego are good places for finding cheap boats.
In Florida check the following:
Nationally (U.S.) check out the following:
Another tack that one could take is to set up their own charity and get someone to donate a boat to them. This would work maybe by taking advantage of some of the ideas in the Free Ministry section and then setting up a church and using it to get someone to donate a boat to you for a tax deduction. This could be a way to get a free or almost free boat in really good condition.
Good luck to all future children of Neptune and Poseidon but remember the saying that we mentioned first. Safety should always be the first rule in dealing with boats.