WASHINGTON—Former Texas Rep. Beto O’Rourke is asking aides to create an itinerary for him to take a solo road trip outside of Texas where he would “pop into places” such as community college campuses, as he considers whether to enter the 2020 Democratic presidential primary, according to a person familiar with the plans.

Mr. O’Rourke’s trip would begin from his El Paso home and keep him away from Iowa and other early-voting states. Mr. O’Rourke doesn’t plan to be accompanied by staff or press, though he may document the trip...