(covers information from several alternate timelines)
While trying to feel "alive" in 2375 after learning of the destruction of the Maquis, B'Elanna Torres would occasionally skydive from a shuttlecraft in the holodeck with the safety protocols off. If the program was interrupted mid-fall, a force field would move her from a horizontal to a vertical position. (VOY: "Extreme Risk")
James T. Kirk's orbital skydiving attempt was cut from Star Trek Generations. It does appear in the Special Edition DVD and the novelization of the movie. The suit that B'Elanna uses is a re-use of the one that Kirk used. Orbital skydiving is also mentioned in the novels Worlds of Star Trek: Deep Space Nine, Volume 1, Preserver and Captain's Peril.