>>244359I have a very similar dream. Almost identical. Just getting a sailboat, and living in it as long as I can. Always staying out of cold weather and always doing and going wherever I want. Once I'm real good at sailing I'd take my family every once in a while for a year-long adventure around the world with them. I'd also try to get known in the internet in certain image boards (such as this one) and take random people for adventures and across oceans for free.
As for the money, besides the starting amount to purchase the boat, living onboard is incredibly cheap. Just slap on some solar panels, and done. The only thing that's left is food, which I plan to purchase with money from selling photographs or any small internet website.
But it's more than a dream now, to me. I'm halfway through getting the money. My goal is 50k. 25k for the boat, the rest for starting out: classes, gear, housing until I get the boat, etc.
Who knows. Maybe you and me will meet someday, and we can go on /out/ adventures with your tortoise. n-no homo