What are the downsides vs. a sailboat?
A. I would rate an exploration of the planet by sailboat an 8 to 9 on the scales of adventure, fulfillment, accomplishment, intellectual challenge, romance and discovery. Comparatively, a bike is about a 5-6 on that scale and I would rate one of these overland expedition vehicles about a 1-3, so that deficit is an important difference to me. From the financial perspective, you can insure a sailboat against all risks for any amount anywhere it is in the world, but that type of coverage for a land vehicle is not readily available. Lastly, the wind, while not actually free when you are paying to keep a sailboat maintained, is not sourced from politically unstable regions, tin-pot dictators or terrorist financing religious fundamentalists.