This chapter is part of a larger study investigating Primary 6 (Grade 6) students’ engagement in mathematical modelling in a Singapore school and focuses on the mathematical reasoning of one of the modelling tasks attempted by a group of students. The task challenged the students to design an itinerary package for a group of tourists intending to visit a holiday resort island. The design primarily included the need to plan a plausible route to cover places to visit while taking into consideration distance, time, and cost aspects framed within certain task conditions. Through a models-and-modelling perspective, examples of the group’s work are presented to show their conceptualisations and mathematical reasoning towards reaching a final considered route.