As the Canadian population ages, there is an increasing demand for senior transportation services that cannot be met by regular public transportation systems. This thesis aims to bring attention to the combinatorial optimization problem of senior transportation. By extending current vehicle routing problem knowledge and computational technologies, we construct novel problem definitions for the Senior Transportation Problem (STP) and the Senior Transportation Problem with Overbooking (STPOB) based on data provided by a partnering non-profit organization specializing in senior transportation services. Solution approaches including mixed integer programming, constraint programming, two logicbased Benders decompositions and a construction heuristic are developed and empirical analyses on both randomly generated datasets and real-life datasets are performed. Constraint programming demonstrates best results being able to solve to optimality large real-life instances of up to 270 vehicles with 385 requests for the STP and up to 210 vehicles with 320 requests for the STPOB under 600 seconds. This thesis would not have been possible without a number of people. I would like to use this space to express my gratitude towards them. Before all, I would like thank my supervisors Professor J. Christopher Beck and Professor Dionne M. Aleman for the boundless guidance, patience, support, as well as all the creative ideas throughout the past few years. Their persistence has inspired and pushed me to places and opportunities that I could not even have imagined previously. Not only have they advised me on technical expertise, they have shown me how interesting and fun research can be. I could not have imagined better mentors for my studies and research. I would like to thank my committee members, Professor Merve Bodur and Professor Chi-Guhn Lee for their time and feedback. Thanks to all the amazing people at TIDEL and morLAB for such a fun and amazing time that I would never forget in my life. They have made the sometimes dull student life shine in bright colours. Thanks to my parents for the unconditional love and support for me to pursue my dreams. Lastly, to Chong, my best friend and beloved husband, thank you for being always by my side to share the bitterness, keep me sane and make me laugh.