The means by which you move forward in your life, and especially to make the best use of the resources available to you. Dreaming of a sailboat can mean that your life direction is important to consider right now.
Sailing on a sailboat that's moving along well can mean your life is moving along well, and you are feeling supported or fortunate.
Being on a sailboat that's not moving or is having trouble can mean you're feeling stranded, stalled, or possibly at a dead end somehow in your life. Think about how best to get things back "on track" or moving again.