[webrobots]

Paragliding. Physically not too difficult. It is more a mental game - chess in the sky.

[korfuri]

Somebody also suggested paramotoring in another comment, which is less like chess against the sky, but may be more accessible depending on where you live.

However they also warned, and this applies just as much for paragliding, that competiting in this sport is significantly more dangerous than practicing as a hobby.