The author doesn't seem to go into why travel-planning software is not successful, except for that it isn't discoverable since people only use it once in a while. I think the same can be said for a lot of services, like handymen (Angie's List) One other reason is I think that travel planning is hard. Getting multiple people to agree on a destination, hotel, fares etc is all hard work. So most people only plan things…
Surely there's a way to do it better than just over text? It's a 4-dimensional (time and space) experience isn't it: "After lunch on day 2 of the vacation, what attraction do you want to visit?", or, "When do we have time to squeeze a visit in that café that all the Instagrammers post about? [Yeah, like it or not this is the reality]". A Miro[1]-like collaborative map would be interesting, every participant of the tr…
What I mean by the "probability distribution" part is, your trip plan isn't really a specific plan - it's a set of possible plans. You may have concerns like, "what if we arrive late on the first day?", or "what if the main attraction for the 2nd day is closed", or "we're not sure at this point where we'll eat", or "oh crap, it's raining today, what do we do?", etc. You have to navigate these questions in your head. I'd love to have a tool that makes this easier.