Designated driver services use company vehicles to deliver drivers to customers. The drivers then drive the
customers from their origins to their destinations in the customers’ own cars; at the destinations the drivers
are picked up by a company vehicle. We typically see teams of drivers assigned to company vehicles serving
customers. When, however, the drivers may be dropped off by one vehicle and picked up by another, a
challenging, novel pick-up and delivery problem arises. In this paper, we introduce two formulations to solve
this problem to optimality using a general purpose solver. In particular, we present a three-index and a two-
index mixed integer program formulation to generate optimal, least-cost routes for the company vehicles and
drivers. Using these MIPs, we find that the two-index formulation outperforms the three-index formulations
by solving more instances to optimality within a given run time limit. Our computational experiments also
show that up to 60% cost savings are possible from using a flexible operating strategy as compared to a
strategy in which drivers and company vehicles stay together throughout a shift
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