Dreaming you are sailing on calm waters predicts you will have an easy time as you make your fortune.
A beautiful sail full of wind indicates you’ll be free from poverty and misery. Dreaming yourself sailing in a small vessel indicates your desires will remain modest and not beyond your means.... Tryskelion Dream Interpretation
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 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. ... A Guide to Dreams and Sleep Experiences
Psychological / emotional perspective: 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. Because a boat or ship is usually thought of as feminine, the sails in dreams can represent pregnancy and fertility. By association, they can also signify how a woman will use her intellect.... Dream Meanings of Versatile
Material aspects: Sails suggest the idea of making use of available power. Often the type of sail will be relevant. Old-fashioned sails would suggest out-of-date methods, whereas racing sails might suggest the use of modern technology.
The colour of the sails may also be important. When we dream of sailing, we are highlighting how we feel we are handling our lives. We can either 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 former is more to do with one-to-one relationships, while the latter suggests a group effort.... Dream Meanings of Versatile