Actually, the "land dweller" would have to exit the spaceship first, then board it again some time later.
This is actually an instructive way to construct a "twin paradox" scenario. Suppose we pick a frame which we'll call the "land frame"; in this frame, a very, very long spaceship is moving to the right at some speed ##v## which is close to the speed of light. The clocks on the spaceship are all synchronized with each other as viewed in the spaceship's rest frame.
At time ##t' = 0## by the spaceship clocks, the "land dweller" jumps out of the spaceship at ##x = 0## in the "land frame" and immediately decelerates to a stop, so he is at rest in the "land frame". (We will say that the land frame clocks read ##t = 0## at this instant, and that the point on the spaceship where the land dweller jumped out is at ##x' = 0##.) At this instant the land dweller's clock also reads zero, since it was sychronized with the spaceship clocks while he was on board the spaceship. Then the land dweller floats there and waits for a while, while the spaceship flies past him; then, after some time ##T## has passed on his clock, he immediately accelerates to speed ##v## and boards the spaceship. The time that he sees on the spaceship clock when he boards (this will of course be a different clock than the one he saw when he exited the spaceship, but all of the spaceship clocks are synchronized in the spaceship frame) will be greater than ##T##.