You will have to do it sooner or latter and actually you can practice raising the sails with the boat still on the trailer. It will not fly off. In calm to moderate conditions go ahead and raise both sails. What powers a sail is the pulling on the sheets, as long as they are loose the sails will just flap around not imparting any power to the boat. Point the boat into the wind to raise them and to lower them. Tighten the halyards and curl around a cleat but make no knots or ties, friction will hold them secure but ready to be loosened in an instant. Slowly veer off from the centered wind direction and watch the sails catch wind. Pull gradually on the halyard until they fill and pretty soon the boat will start moving. Do not panic in a puff of wind just gradually release the main sheet. You can also use the rudder to direct more or less wind into the sails by moving the boat closer or farther away from the wind direction. Wish I could be there, love a good circus act.
