So what’s the best way to climb your mast? Depends on your boat, your age and the money in your wallet. Any way you come at it, climbing a sailboat mast is going to be a compromise and there isn’t going to be any one choice that’s right for every situation or person. As for me, I think I like the climbing harness and a block and tackle the best… since I have a pretty shallow draft wallet. Just remember to be really careful and err on the side of too much safety than not enough when you climb your sailboat mast.