Unfortunately, buying a boat is expensive, and I have no knowledge of sailing.
So I've found something that is the same concept, but might work even better: bicycle touring. A world class touring bike (a Surly Long Haul Trucker) can be had for $1200. Much cheaper than a sailboat. A good tent can be had for ~$300.
I've made a deal with myself that I have 2011 to either get back into school, get an interesting, fulfilling job, or have founded a site that is producing enough money for me to work on it fulltime. If I don't accomplish this, I'm selling everything, loading the dog into a trailer, and riding across the country.
You'd be surprised. Where I'm currently at (Montreal) there's a lot of 40-year old ~21 foot sailboats going for $3-4k. Me and a buddy planned to buy something this summer, but he spent his share of the money on travel. I was too lazy to learn to sail and don't like carpentry and other crap that goes into maintaining a boat, so I decided not to get a boat by myself.
Even when you factor in repairs, harbor fees and the possibility of having to write the boat off after 1-2 years because it's spending all its time in the water (most of the boats we looked at were dry docked for most of their existence), it's still cheaper than rent.
About touring bikes, it really doesn't matter what you tour on. I've known people who've toured on Wal-Mart bikes (not a good idea), 70s 5-speed bikes, track bikes (also not a good idea), double-stack welded tallbikes, etc. There was even a guy riding a BMX backwards across the USA for charity.
I have a bunch of friends that swear by the LHT, but I like to tour on late 80s-early 90s rigid-fork steel mountain bikes (all the rigid-fork mountain bikes made today are suspension-corrected, which makes them useless for just about anything). On mountain bikes the rear rack sits lower and handling gets smoother as the rear is loaded, which isn't always the case with road-type frames. This means you can go with rear panniers only, which is great because front panniers really mess up handling. As a plus 26" wheels and tires can be found almost anywhere, and are usually stronger than 700s.
If it's the cost of a boat that concerns you, take a look at this Instructable series, wherein the author details how he got a free yacht and set about repairing and improving it:
Unfortunately, buying a boat is expensive, and I have no knowledge of sailing.
So I've found something that is the same concept, but might work even better: bicycle touring. A world class touring bike (a Surly Long Haul Trucker) can be had for $1200. Much cheaper than a sailboat. A good tent can be had for ~$300.
I've made a deal with myself that I have 2011 to either get back into school, get an interesting, fulfilling job, or have founded a site that is producing enough money for me to work on it fulltime. If I don't accomplish this, I'm selling everything, loading the dog into a trailer, and riding across the country.