To dream that you are sailing represents how your life is going and how you are able to handle life's problems. You are in control of your life. The dream may be metaphor that things are "smooth sailing." If you are sailing through the rough seas, then it means that you will overcome life's difficulties. If you are sailing against the wind, then it indicates that you are experiencing some struggles in your waking life.

To dream of sailing on calm waters, foretells easy access to blissful joys, and immunity from poverty and whatever brings misery. To sail on a small vessel, denotes that your desires will not excel your power of possessing them. See Ocean and Sea.