Who says you need a big boat for a big adventure? Self-sufficient sailors have long turned to sturdy little crafts for passages in challenging waters from lakes to oceans. Not only are small boats simpler with fewer systems to maintain, they are also typically more affordable to buy and refit.

Some of our favorite great little boats, all of which have proved themselves many times over, are available on the used boat market. If you’re fortunate enough to find one in good shape, you probably won’t be the only sailor interested. Whether you’re looking to trailersail across the country, cross an inland sea or even sail around the world, these five boats can take you there.