There are multiple ways to get this started, and not all of them have to be direct to consumer.

There are companies who specialize in organising travel, which could be aided by better software.

Personally, I would pay for a travel planning app, but the pricing structure would have to be right since I'm not going to pay for a subscription for something I use infrequently.

I think the key thing here is that travel is already very expensive, so there is money to be made here in improving the process, but skimming some ad/referral revenue off a large volume is the easiest way to do so.

I looked for a travel planning app when I went to Mexico City last year and was generally not impressed with the offerings, so I just ended up pinning everything I wanted to do in Google Maps.

To continue with the theme of people paying for things in this area: My wife still buys travel books for cities. Books are definitely not my favourite medium and I would definitely consider paying for the information online.

A travel book will run you 20 bux easy. It will be perceived as super cheap at 10.

How many people would buy a 10$ app for a guidebook for a specific destination (city or country), even if it was infinitely more performant and native than the book.

>How much would people pay for a trips app?

TripIt Pro is the standard and costs $49 per year. It's not really for leisure travel but for business/productivity.

I’m not sure why you say it’s for business. I do a lot of business and personal travel and it’s great for both. Organizing trips with friends and family is much easier to coordinate with tripit and my boss couldn’t care less which hotel/flight I’m on.

The pro features specifically is mostly just alerting, not tied to personal/business.

I have never used the sharing features much. I say business but perhaps what I mean is frequent travel. I.e. having enough flights and hotels on your calendar that they're hard (or at least a bear) to keep track of.

There are still folks that recommend AAA memberships for leisure travel, and that start at $52/year (plus "admission/activation fees").

On the flipside, I see so many people these days using a wild combination of improv wandering, personal recommendations from Uber drivers, Airbnb (or VRBO or whatever), and Yelp, that I think a lot of leisure planning has gotten sometimes too weird and undirected/semi-directed versus classic trip planning models.

Weird, maybe. I would say that relying on Yelp or Thrillist or Eater or whatever is the top result on Google still ends up with everyone crowding the same (weird) places.

Not much different from traditional trip planning though, if you are just swapping from "top AAA recommended" (or "top guide book recommended") to "top Yelp recommended". Having a person involved in something like a AAA trip plan added some variety in terms of inter-personal suggestions/customizations. (Or specialized/niche guide books.)

Arguably Yelp has a massive (maybe a bit stalkery) version of that inter-personal suggestions/customizations at your finger tips in that you can come to get a feel for individual reviewers, especially area Elites, and how well their tastes align with yours. It is possible to find interestingly curated lists of places in an area if you work at it, which isn't that different than the guide book era (though maybe weirder). Certainly not as convenient as paying someone else to do all that trip planning work.

I've been using, mostly, travefy, and haven't had the time to check Trip It (I think I tested it years ago, and had something I didn't like)

Is it better?

It hasn’t changed noticeably in the better part of a decade. But it works really well for me (albeit not the prettiest app in the world)