A computer implemented method for generating itineraries comprising: receiving a departure location, a destination location and a departure time; identifying a first intermediary location between the departure location and the destination location; identifying a first intermediary time that a user of a ground transportation device departing from the departure location at the departure time is projected to arrive at the first intermediary location; identifying a first weather forecast for the first intermediary location at the first intermediary time; characterised in that the first weather forecast comprises a first probability of a specific type of precipitation at a specific rate; and in that the method further comprises: identifying a second intermediary location between the departure location and the destination location; identifying a second intermediary time that a user of a ground transportation device departing the departure location at the departure time is projected to arrive at the second intermediary location; identifying a second weather forecast for the second intermediary time at the second intermediary location, the second weather forecast comprising a second probability of the specific type of precipitation at the specific rate; comparing the first weather forecast and the second weather forecast; selecting either the first intermediary location or the second intermediary location based at least in part on the comparison; and generating an itinerary that includes the selected intermediary location. receiving a departure location, a destination location and a departure time; identifying a first intermediary location between the departure location and the destination location; identifying a first intermediary time that a user of a ground transportation device departing from the departure location at the departure time is projected to arrive at the first intermediary location; identifying a first weather forecast for the first intermediary location at the first intermediary time; characterised in that the first weather forecast comprises a first probability of a specific type of precipitation at a specific rate; and in that the method further comprises: identifying a second intermediary location between the departure location and the destination location; identifying a second intermediary time that a user of a ground transportation device departing the departure location at the departure time is projected to arrive at the second intermediary location; identifying a second weather forecast for the second intermediary time at the second intermediary location, the second weather forecast comprising a second probability of the specific type of precipitation at the specific rate; comparing the first weather forecast and the second weather forecast; selecting either the first intermediary location or the second intermediary location based at least in part on the comparison; and generating an itinerary that includes the selected intermediary location. identifying a second intermediary location between the departure location and the destination location; identifying a second intermediary time that a user of a ground transportation device departing the departure location at the departure time is projected to arrive at the second intermediary location; identifying a second weather forecast for the second intermediary time at the second intermediary location, the second weather forecast comprising a second probability of the specific type of precipitation at the specific rate; comparing the first weather forecast and the second weather forecast; selecting either the first intermediary location or the second intermediary location based at least in part on the comparison; and generating an itinerary that includes the selected intermediary location.