> One awesome thing this would allow is for people to create and curate special-interest travel guides.

I think there's HUGE potential in an online service that takes care of all the aspects of a trip. Right now you have the choice of either doing everything manually (which is a big time sink) or going on a package tour (which is bland and one-size-fits-all). In between you've got a few options like Expedia and Travelocity, but they're more like extensions of the package tour idea than a rethinking of the concept.

In my vision, you'd give it the dates you want to travel, where you want to go, your budget, and access to your social networking accounts (so it can figure out your interests/hobbies). Then it uses the data you've given it along with preexisting curated travel data (which could be based on crowdsourced info, both from previous customers and from 3rd party sources) to create an optimized & customized travel itinerary and take care of all the purchases (plane tickets, hotel reservations, Uber reservations from the airport to the hotel and between sightseeing locations (if needed), tickets for different sightseeing locations, etc.) so that you just have to pay once, to this service. You don't have to worry about when places are open/closed, how long it takes to get between them, etc. - that would be automatically calculated (should be pretty straightforward with Google Maps API access).

Then you'd want to have an associated smartphone app that will (in real-time) display the itinerary, give directions between the different places, suggest restaurants to eat at (maybe make reservations using OpenTable), etc. The itinerary could even be dynamic. For example, if there's an outdoor activity planned and it starts raining, it would automatically rearrange your itinerary as necessary, etc. You could use GPS and/or NFC at museums and other places to play back audio explanations of various exhibits (they already have this at many museums, but you have to pay extra for the privilege and wear an iPod or some other clunky device for the duration of the tour).

I have to ask:

Why is there so much emphasis on planning a trip? What happened to mapping out a few attractions and spending the rest of the time stumbling around letting your feet and eyes be your guide? All my favourite trips have resulted from pure serendipity and the rewarding experience of discovering something purel by accident.

... you mean a travel agent?

No, travel agents fit into the "package tour" group that I mentioned above. In my experience, travel agents have provided a one-size-fits-all experience - stale and boring.

This seems quite nice. It has a solid UI and is certainly heading in the right direction, but lots of work remains to be done. For example, flight booking needs to be integrated, and a smartphone app isn't available.

They say the service is completely free, which IMO is a big mistake - the right approach is to be responsible for all the payments and then charge the user just one time, which not only allows you to add a fee on top (your primary revenue source) - it removes one more pain point for the user.

Wouldn't that require having arrangements with all the carriers?

Also, I probably wouldn't give several thousand dollars to an intermediary, especially when some airlines have "special" policies that apply to tickets booked by proxy (e.g. the proxy needs to request changes, not the end user).

Travelers not willing to do some legwork should not be surprised if they find themselves confined to proven tourist trails. And in fact that's what many people want.

The ebooks really are frustrating aren't they - I blame this mostly on apples iBooks though which is best for novels really.

We're exploring digital travel guides over at coolplaces.co.uk and are busy building out content (uk only for now). So it's interesting to read your ideas on this as they are close to ours. It's early days yet for us, and we have a lot of ground to cover before we get to custom travel guides created by users, but it is on the roadmap, and these are exciting times to explore travel info. Would be interested in your comments on our site.

Something that has hit me more times than is ideal is opening times. A surprising number of travel guides do odd things like say 'open Tuesday to Sunday, closed 1st Sunday of the month.' At a quick skim its easy to miss the 2 key things, closed some Sundays, closed all Mondays. And unhelpfully the format of the information is often inconsistent within the same publication. Invariably the info is out of date anyway, and prices are considerably higher than the guides states. We usually used Lonely Planet or Rough Guide, but the lack of up to date opening times was a continual pain (out of date prices is annoying, but you can spend more and get in, but if the place is closed, you're stuck).

I understand your frustration with how the travel guides under-utilize potential of new media.

I would like to ask you, though: do you find electronic renditions of Lonely Planet (for either e-ink reader or tablet computer) an adequate substitute for the paper version? I understand that they could be much better in theory, but are they at least not worse? I am going to go on a tour around Europe and I seriously consider buying an iPad or a e-ink reader in part for Lonely Planet, because they should be easier to carry around than even a single travel guide.

I've used Lonely Planet guides extensively in paperback and somewhat in Kindle form. The Kindle versions are worse in terms of usability. This is partly because the maps are usable in paper form, where it is easy to flip between the map and the legend, or indeed where they are sometimes on facing pages visible at once. The way they make the electronic versions, the maps often have a low-res overview and legible sections on separate pages. Want to move north on the map? Go forward two pages! That's just silly, a UI worse than MapQuest ten years ago.

What's good about LP on Kindle? If you happen to be travelling very light to several first-world destinations which are not covered in any single book, you can definitely save space and weight. Also if you buy the book more for the prose than the maps, it could be all right (with an iPad and a local SIM card this could work well enough, again assuming you don't travel where people are very poor).

I just got back from a trip to hawaii, and still bought the Kindle version of the LP guide (and another) while there, rather than a physical print book, because I could do it from my hotel room without putting on pants the day before picking the next day's activity. A secondary consideration was 3 less things to carry around.

The books really could have been vastly better -- there were some clickable urls (when viewed in the iPad 3 kindle app)

Would there be a way to combine guides like that in OpenStreetMap? That might be a better option than Google Maps.

We tried to do something along these lines with journly.com. We've since pivoted away and are working on something else, but I agree it's still a problem that needs to be solved.

Care to share why you pivoted away from that idea?