We want to break down some of the pros and cons to doing each activity.
Kiteboarding has a steeper learning curve and lessons are required to learn this sport. Kiteboarding in our opinion is a better sport for those wanting to jump and freestyle tricks.
Winging as more of a soulful feel much like surfing. The beauty of winging is that you can learn on your own, and don't need to have lessons. We feel lessons are great for learning wind theory and basic wing and board skills. The sensation of gliding across the water on foil is a feeling like no other sport.