The disclosure includes embodiments for optimizing a route selection for a highly autonomous vehicle (“HAV”) which provides an automated driving service. In some embodiments, a method includes: generating a set of candidate routes for a journey; aggregating external data describing one or more external factors which limit an availability of the automated driving service while traveling along the candidate routes; determining a first value for an optimal degree of automation for traveling the journey based on a condition of the driver and the preferences of the driver; determining a plurality of second values for a plurality of possible degrees of automation for each candidate route based on the external data; and selecting an optimum route from the set of candidate routes by comparing the first value to the plurality of second values to determine which of the candidate routes has a second value which is closest to the first value.