Sailboats are associated with your ability to navigate life’s challenges and weather emotional storms. To see a sailboat in your dreams represents your ability to navigate through your personal challenges. If you are sailing along easily, it could indicate that you are handling life’s challenges well. On the other hand, if the sailboat is in rocky waters, it could indicate that you are not able to handle what comes your way very well. Look for ways to detach from your problems before getting emotionally involved. Alternatively, seeing a sailboat in your dream could point to your emotional state. If the sailboat is on calm waters, it suggests that you’re feeling peaceful, calm, and serene. If the sailboat is in the midst of a storm, it suggests you are feeling out of control and at the mercy of a force beyond your control.