The steadily growing popularity of grocery home-delivery services is most likely based on the convenience experienced by its customers. However, the perishable nature of the products imposes certain requirements during the delivery process. The customer must be present when the delivery arrives so that the delivery process can be completed without interrupting the cold chain. Therefore, the grocery retailer and the customer must mutually agree on a time window during which the delivery can be guaranteed. This concept is referred to as the attended home delivery (AHD) problem in the scientific literature. The phase during which customers place orders, usually through a web service, constitutes the computationally most challenging part of the logistical processes behind such services. The system must determine potential delivery time windows that can be offered to incoming customers and incrementally build the delivery schedule as new orders are placed. Typically, the underlying optimization problem is a vehicle routing problem with a time windows. This work is concerned with a case given by an international grocery retailer’s online shopping service. We present an analysis of several efficient solution methods that can be employed to AHD services. A framework for the operational planning tools required to tackle the order placement process is provided. However, the basic framework can easily be adapted to be used for many similar vehicle routing applications. We provide a comprehensive computational study comparing several algorithmic strategies, combining heuristics utilizing local search operations and mixed-integer linear programs, tackling the booking process. Finally, we analyze the scalability and suitability of the approaches.