1- When we dream of sailing, we are highlighting how we feel we are handling our lives. We can cither work with the currents or against them.
If we are sailing in a yacht there is more of a sense of immediacy than if we were sailing in a liner.
The first is more to do with one-to-one relationships, while the second suggests more of a group effort.
2- To be tacking - sailing against the wind suggests that we have created difficulties possibly by setting ourselves against public opinion.
To be sailing with the wind means we are using opportunities to the best of our abilities.
3- Sailing suggests a sense of spiritual freedom and the ability to use our intellect. [1]
The images in sailing lend themselves to depict human endeavours to work with the tides and influences of life. Dealing well with wind, waves: suggests being able to meet internal and external pressures, emotions and drives, and using them to advantage. Being overwhelmed, sinking: finding emotional, sexual drives and anxieties too much to cope with.
See also: boat, ship. Idioms: plain sailing; sail against the wind; sail close to the wind; sail into something; sail under false colours; set sail; trim one’s sails; take the wind out of someone’s sails. [2]
A beautiful sail full of wind shows that you will be free from poverty and much misery.
If you are on a small vessel this shows that your desires will remain modest and not beyond your means of earning them. [3]
If not, then expect trouble and worry, according to the severity of the storm in your dream.
The smaller the Boat, the greater your success, or your misfortune. [4]
To sail on a small vessel, denotes that your desires will not excel your power of possessing them.
If the sea is stormy, you are troubled about a personal situation. [6]
2. On the way to achieving whatever one wants to. [12]