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Totally agreed! It's a problem I'd love to see solved well. I've wanted a route planning / mapping app that can achieve advanced features for a few years now. I'd love to build it myself but honestly, I'd much more excited that it could exist rather than it existing under my control and for my profit.

* Multi-modal planning: where walking, transit, biking, and driving can be independently selected for each leg of the journey (in a multi-stop trip)

* Travel breaks with duration: for a multi-stop trip, allow the inclusion of estimated stop time (e.g. I plan to stop for a meal at a particular restaurant on my upcoming road trip and I intend for that stop to take 1.5 hours). That stop time would then affect the ETA for all stops along the way and may even impact which public transit options are available at later stops.

* Multi-day journeys: for more specifically planning road trips or vacations.

* Constraints on the journey: the most familiar of these (which is already somewhat implemented in the popular maps apps) is whether a business will be closed when you arrive. Others could involve weather predictions (on a multi-day, multi-stop trip I only want to go to the beach on a day it's not raining), daylight hours (I don't want to go to the park after dark), etc. I would expect this feature to let users provide their constraints and the planned route would warn users if their constraints aren't met.

* As mentioned in another comment, route comparisons: for single-stop or multi-stop trips, it should be incredibly simple to compare two or more routes. This should be possible prior to travel _and_ while en route. CityMapper provides some amount of this feature: while on a route, you can return to the form where you input your origin and destination and can get an idea of comparisons.

* Another comment (and the article) mentioned exploration while en route: it should be trivial to explore the map in a way that's completely unrelated to one's current trip. Similarly, it should be easier to search for locations that are nearby your route (that is, wouldn't take more than X amount of time out of your way).

An obvious stretch goal after having these features would be to allow for trip optimization given a number of modes of travel, destinations, timing constraints, ordering constraints (want to pick up food before I go to the park for a picnic, so restaurant must come before picnic), and even proposed start and finish times for a trip. This of course falls into the realm of the traveling salesman problem, but if I'm able to reasonable build a few proposals for routes manually (by setting arrival / departure times and choosing transport modes in my maps app) one stop at a time, an app could certainly check a few permutations.



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