Wing-on-wing is a sailboat term for sailing directly downwind on a run and deploying the main sail to the one side of the sailboat (e.g. starboard side) and flying the jib sail on the opposite side (port side) as depicted in this photo on Convair Sailing Club sailboat Victory #634 with Victory #632 following close behind it.

Regatta - Sailing on San Diego Bay

Regatta – Sailing on San Diego Bay

Usually a whisker pole is utilized to help maintain the jib sail in position and to prevent it from folding when the wind changes. This technique attempts to maximize the speed by having both sails filled to max by the wind as opposed to the main sail obscuring the wind from the leeward jib.

The Skipper needs to read the wind and the sails and finely adjust the sails and course to maintain the best heading to achieve best speed by keeping both sails filled for maximum power.

  1. After  turning around the mark, the skipper will head in the desired downwind direction on the next leg of the course.
  2. Crew #1 will already have the whisker pole ready.
  3. Crew #1 will step up to the foredeck, grab and control the jib sail, and insert the pin on the front end of the pole through the clew.
  4. Crew #2 will control the jib sheets to assist
  5. Crew #1 on foredeck will push sail out to opposite side as the main sail
  6. and securely attach the inboard end clasp to the ring on the front side of the mast
  7. and once secure return to the cockpit