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It's a bit different when it comes to business travel. I'd use and pay for travel planning for business where my schedule can take me to out of the way places and the schedule can change frequently. There is a tier of business traveler in small businesses or who are self employed and need an economical itinerary with specific attributes for flights and hotels, but who don't want to stay in crappy places. I've spent far more time on HipMunk and on the phone with hotels.com and re-booking flights than I should have to. Maybe start a manual service, learn how this stuff works and then automate it.
Or you could start using a good travel agent, as they would do these things for you.

Is this a good time investment for you? You have a choice on what you spend your time on. You could install your own plumbing, write your own t's and c's etc. or you could pay someone to do it.

AirBnB is a solid exception to the "must be daily users - 20% retention" statistic. No way is their average user base a daily user.
Plenty of other exceptions: a large % of eBay users probably don't use the site every other day.

Selling on eBay or renting a property are highly intentional decisions: trip planning is something that will happen. The trip itself is intentional, but the exact itinerary will vary, and the lack thereof won't prevent the trip from occurring.

Don't forget that there's a distribution around the mean. You'll probably find plenty of outliers. It'd be interesting to see the graph MixPanel's guy is basing his estimate off of.
I don't agree that 20% retention statistic is a good way to view it at all. There are tons of exceptions to that rule - Amazon, Kayak, Turbotax, or even TripAdvisor. I often view that as entering one's normal "workflow" through whatever it is they are trying to do - it's a rarity, and there is a good chance that a fringe app wouldn't make it.
There are two unique userbases for AirBnB - renters and renters. Renters may not have a 20% daily retention but I would bet that rentees are much closer to 20%.

On top of that, AirBnB is a marketplace. I would imagine that marketplaces are affected more by supply and demand ownership than daily retention.

I was going to propose the exact opposite: renters who want to keep their ratings high go back frequently to answer inquiries while each individual rentee only goes on the site occasionally when traveling.
I chose not to use "owner" because not all people listing on AirBnB own their property, but I think we were thinking the same thing. People listing properties almost definitely have higher retention than travelers.
Let's call it a rule of thumb. There are always exceptions in startups.
Based on the comments to the article, this is a year old (still valid, just a bit old)
As someone who is working on this idea currently, this post has really got me down.
Are you working on the idea, or working on validating the idea?
Time to prove him wrong! :)
I would very much like to be wrong on this one.
I've got a fairly unique take on local trip planning @ 80%. If you want to chat, shoot me an email!
This post is pretty light on justification.

20% retention is neither good nor bad. There are a lot of businesses that survive on one or two events a year. If you are in the business of selling metrics software (like his friend at MixPanel), you probably want people to come every day.

The "I don't have room in my brain" argument is just silly. I can open my refrigerator and see hundreds of different brands. There are millions of websites, of all kinds! Should we stop building websites because there are a lot of them and it's harder to differentiate?

It's pretty hard to swallow this kind of advice from a guy who founded a blogging platform in 2008, 5 years after blogger.

Anyway, as our man PG likes to say, just go make something useful. The rest will take care of itself.

Do you have a business model wherein people will pay you money? I can only see this working for B2B. If you can't answer why it will be different for you, rethink your business.
Just make sure you're validating your idea as you go instead of just building it, and you'll find out for yourself if its worth continuing.

As depressing as it sounds, there's little point in continuing product development without solid validation. Its a problem I ran into at my previous startup - a good product, but just not needed by enough people.

Don't get dejected. A person can probably write a similar post about every great company that will get started in the next 10 years. Prove cynics like that wrong.
A couple of guys I know did a small travel planning website. It's plastered with ads. I think they have almost not touched the site after they launched it, and it's doing ~6-8K€ monthly with ads (traffic coming from SEO).

Don't get discouraged by a guy explaining why it can't work according to its theory.

Atleast the fact that this was written and its currently at the top of Hacker news says that this pain exists. The author of the post is saying that no solution has been found yet. You should consider this a blessing in disguise and not get disheartened. There are perhaps atleast two things to take away from this.

1. The problem exists ( and is a genuine problem that quite a few people care about! ). 2. A good solution has not been found yet. ( also kind of good for you! ).

Apart from this, it also gives you a lot of information about the industry. Especially the discussions that are happening here. So, why dont you consider this a loooot of great feedback and go back to the drawing boards and go disrupt this industry ?

Same here. I've been doing user research on the subject, and while there are some clear problems to solve they might not just be worth solving.
No daily usage, not enough trips and also it is impossible to build a multi-billion corporation out of an SEO play. Too bad TripAdvisor won't work. /S
This is a great observation! I'm two months into this "digital nomad" experiment, and the biggest pain has been lack of central organization for my schedule, todos, costs, sights-to-see, etc.

My interpretation is that the domain is simply too big, and the field of "personas" so varied that finding a critical mass of core users around common use cases is nigh impossible. Even within those identifying as "digital nomads", you have adventure tourists, travel-blog content marketers, $100/hr front-end consultants, cultural commentators, resilience quacks, and so on.

Look at a site like TripAdvisor, which does a great job of aggregating the most basic reviews of restaurants, hotels, etc., and even it contends with enormous problems like data rot, internalization, etc.

I suspect that, if the "long-term travel" community continues to grow, there will emerge specific niches that could reach that critical mass needed for an MVP of a serious travel planning app. For now, trying to parse through google results for "apps for digital nomads" is something like a nightmarish goose chase through an illegible jungle of travel blog shills.

What's a "resilience quack"?
Seriously. Inquiring minds want to know.
Sounds clever, but it really doesn't stand up to scrutiny. There are countless profitable businesses that aren't things you use daily (Amazon, E-Bay, AirBnB, etc etc.) Conversely, how many sites do you really visit daily? I visit, like, four. (Gmail, reddit, facebook, hacker news)

Travel planning software is difficult because there's so much competition and a lot of political forces trying to keep the newcomers out.

Eh, Amazon gets used a few times a month by a whole lot of people. Ebay definitely has addicts. AirBnB fits your theory better, but I think they managed to get noticed by being truly disruptive.

When you first hear about a travel planning site, it probably doesn't just happen to coincide with a time you're planning to travel, so best-case scenario is you bookmark it, which just goes into a giant list of bookmarks that you'll never look at again.

And when you need to plan a trip, you'll just go to expedia or hotwire or some other site that's gotten burned in your brain through advertising. Or you'll just google flights. Because that's the simplest thing to do and it comes up with pretty decent prices.

>I think they managed to get noticed by being truly disruptive.

A company is not "truly disruptive" before it's disrupting something. I'll bet there are thousands of apps and services out there that have ideas that could potentially become disruptive if they gained traction. Many, maybe most of these will never go anywhere.

I bet you're right. Luck plays a huge, huge factor. And knowing the right people.
Airbnb from the beginning was an experience set apart. We stayed in Venice on my honeymoon and we had perfect local recommendations by a schoolteacher who lives there. We stayed at her house, and had breakfast with her every morning. It wasn't merely disruptive in the abstract sense. It is a better experience than being in cold tourist hotels.
If only we had some combination of software and people with expertise in destinations. Maybe we'd call it a travel agent or something like that.

That was snarky. But it points to the historical problem here. Most travel agents didn't/don't have a lot of expertise outside of fairly narrow domains. And they mostly depended on commissions from pretty routine stuff to subsidize labor-intensive planning for oddball itineraries--which I'm guessing can't be easily codified in software.

In fact, I'm sure there are plenty of competent travel planners but they cost money--i.e. are luxury goods--and most people don't want to pay the money.

Do people still use travel agents? The only time I used one (trip was a gift) we had a bad experience. I think pretty much all the younger generation/tech savy people plan their own trips online manually.
A good travel agent makes things so much smoother. Large chains get economies of scale so you don't pay much more than online/manually, but having all the bits and bobs sorted (courtesy calls if anything changes, transfers, etc.)
Some do. (My dad does for one.) For certain types of trips a lot of things aren't online and, even if you do a lot of your own research, it can be easier to have someone else do all the email and even faxing associated with making the actual reservations.

I also sometimes use one myself in specialized circumstances such as when I'm doing a pre-arranged adventure trip of some sort and the company is familiar with logistics and other activities to add-on.

Why not target travel agencies instead? Agencies can create/manage itineraries, hotel reservation & bookings, destination maps, etc? This will get you paying customers and daily users.
People don't buy cars or get married very often either, but there are plenty of tools to help with those processes.
Business travel might be an exception. Especially for companies who have to manage travel for their employees, and business travelers who want utility features that increase their productivity. Some ideas:

- Incentivize employees who share rides from/to hotel/airport traveling on same dates/destinations

- Show dates for destination that maximizes networking opportunities (in between conferences)

- Show locations with wifi in-between meetings

- Locations with ambiance ideal for business discussions

- Expense capture to identify opportunities for deals (employees love Starbucks during business trips, sign up for corporate deals)

For those solving these sorts of problems, you might wanna to check this out - https://developer.concur.com/devcon/PerfectTripFundAwards

This was my first thought, every big corporate I have worked for had at least one person or sometimes a whole department managing employee travel.
Having thought about this idea in the past, I can say that one of the difficulty lies in the fact that the market "seems" really large, when in fact, you can only address a limited portion of it. People have different tastes and goals in what they want to accomplish in a "trip", and because the market seems so vast and large, the idea tends to gravitate towards the middle ground. You might satisfy a wide array of people, but none of them will really "love" your product. So rather than daily usage, I think the problem is of segmentation first (and competition, etc following...).
The problem with travel planning isn't frequency of use: as other people have pointed out, Zillow and Cars.com are used infrequently but make money.

The problem is generating a consumer willingness to pay. Kayak has a commission on every sale, so their business model is baked in. But a travel planning site will need to get customers to pay extra, in some way, and they're reluctant to do so.

Travel planning is something that people have never paid for directly -- travel agents used to extract their fees invisibly -- so a travel planning company will either need to sell the travel themselves and collect commission like existing travel sites, or create a new market.

Sounds absolutely perfect for affiliate-sales and ad-supported to me.
There are tons of travel affiliate programs, but none of them pay squat because the root problem is that "leads" are common, but paying customers are rare. It's a bit of an overgeneralization, but it isn't totally absurd to view the entire travel industry as a massive lead-gen operation for hotels and (to a lesser extent) airlines.

About the only thing you can do in travel is find some way to make something essential (housing, transportation) cheaper than it already is. If you can't do that, you're a middleman, and the game of the middleman is competitive and well-defined.

Zillow being used infrequently is an assumption. Real estate investors (and those that would like to be) use Zillow almost constantly because it offers some seriously helpful data that is vital to helping with good investment decisions -- and with real estate, you can never have enough data. I'm on Zillow multiple times per day. I also travel enough that I am Platinum in United, yet I have never used a travel planning site, nor do I actively look for one when getting ready for another trip. I use Trip Advisor for my preliminary hotel hunt, for restaurants. For attracticions, Trip Advisor works but so does a normal Google search. Travel Planning isn't 'painful' to me; at least not enough to use travel planning software. I just don't get the value or the problem it purports to solve. I do however, generally love TripIt Pro because there's nothing worse than looking for a confirmation number among multiple days worth of emails while standing at some counter or another. TripIt solves the very real problem of disorganized travel information. Before I used TripIt, I would have to hand-enter the ibro into my phone's Calender. But a travel-planning site? It would have to be really compelling to get me to invest the time to join yet another service. For 'challenging' destinations like India, it could be very valuable, but only if the quality of the information was better than I can find on my own through Google. There'd need to be more than just a bunch of third party APIs, there's need to be some original content. Trip Planning software is a hard sell because I don't find a week long trip to St Tropez or Austin that hard to plan.
Concur on that assumption. Real estate sites in general have a huge amount of passive traffic that can generate advertising revenue. Women in particular have a huge affinity to just browsing listings for fun and aspirational purposes. Whilst Zillow isn't ad driven, know a fair number of sites that rely on that. Source. Work in the space.
Zillow makes most of its money from ads for real estate agents.
Any good real estate investor is accessing MLS listings directly, not browsing Zillow. I don't know anyone who takes Zillow's rent estimation or neighborhood trends numbers seriously, nor who scouts deals on their site.
It's a combination of frequency-of-use and pain-of-problem. You use Zillow infrequently, but when you do use Zillow, you're like, "Holy shit guys, this is my house! It costs hundreds of thousands of dollars and I have to live in it for years!" You're more incented to seek out really good tools.

The problem with infrequently used sites comes when the pain point is fairly small. Even if that pain is reduced a LOT by the site, down to almost nothing, if the absolute magnitude of the pain of the problem is low enough, it's just not worth it for people to hunt down their vague memories of a site and try it out and see if it's any good and learn its process. They'd rather accept the pain.

Zillow is an awful tool (data quality is infamously bad), but it is fun infotainment that gets eyeballs to hand over to agents, and those agents get a huge commission due to the oligopoly of real estate agent industry, so they can pay large referral/ad fees to zillow.
I'm in the market for a house now, and I use Zillow/Redfin every single day at the moment. I'm right there in the "I love this thing" state. I haven't purchased a home before, so it wasn't until now that I got to this point.

You're totally right that monetization is the next concern though.

In UK they even refer to this as "Property Porn" - people actually spend surprising amount of time looking at homes, since it's their biggest purchase, and largest asset. This is one of the reasons Zillow's USP was "estimates" - yet another reason to come back weekly and check how your home changed in value.
I guess the same could be true of travel planning, as well? Even though frequency of purchase is low (although not as low as a house), I can imagine the right kind of escapist travel planning site bringing back people every week to plan dream trips or vacations, however expensive or impractical.
This article rings very true, but on the other hand I've thoguht the same thing about a dozen other things that seemed dead until someone came along and did what seemed impossible.

When Myspace was neglected and Livejournal stagnant, a lot of small actors tried to fill the void but there was absolutely no money to be made and I predited them all dead within two years. I was almost completely right.

Kind of surprised that the OP hadn't mentioned Hopper, the travel startup that was founded in 2007, promised to bring "big data" to travel discovery, and still hasn't much to show for $22M in venture funding: http://techcrunch.com/2014/01/20/why-travel-startup-hopper-f...

But I agree with the OP. Travel planning is a rare luxury, even for the rich. And I don't know what it's like to be rich, but when I find time to travel, I put a loose itinerary together and then improvise most of the way, with occasional lookups on TripAdvisor. There's not really a travel service that can meet the needs of wanderlust.

I had to laugh when I saw this headline.

I'm planning a road trip. And I have been actively searching for a "road trip planner" site.

Whatever Yahoo had at the link he mentioned apparently is gone; it just goes to the Yahoo Travel page.

And everything else I found was complete garbage. "Wrap a Google Maps Directions page with something to put pins in the map near the route for certain categories of attractions" is as far as any of them went.

I don't know what Yahoo's "Trip Planner" was about, but given the overall lack of ANYTHING like a decent road trip planner available, I'd have to guess that it also sucked. Otherwise some of the competing sites would have stolen at least SOME of the obvious features.

What was missing, you ask?

1. Some way to tally up a list of interesting sites. Showing me sites along a route is only about 20% of the way to being interesting; before these sites I could Google cities on the way to find destinations to visit. Actually providing more value than Google already provides is critical.

2. A way to print out area maps and contact details for each of the interesting sites.

3. A way to sort the sites and travel details by day (I'm planning a multi-day road trip).

This is for the MVP, and shouldn't take a competent developer more than a week working with Google APIs or equivalent. A good developer should be able to crank this out in a day or two. I'm tempted just so I can use the functionality to plan my trip!

I have to assume that the dozen or more sites that I looked at were made by people thinking "I'll make a road trip planner!", but who had never taken a road trip. Or who were copy-and-paste developers who could figure out just enough of the APIs to get a basic Google Directions view going, but more complexity was beyond them.

Bonus features (post MVP):

* List the cities at both ends of the road trip and the KINDS of places you might like to visit, and suggest various route options along with the unique stops you could make on the way.

* After you list the places you want to go and how many hours you want to spend at each, plan the driving stops and an optimized order of visiting the destinations. "Day 3: Get up, go to X restaurant near your hotel, drive 2 hours to Y museum, lunch at Z restaurant, then spend 3 hours at the museum across the street..."

* Include AirBNB locations on the map in addition to hotels, but ONLY show both near the end of a day's drive (corollary: give it a range of how many hours you want to be driving per day).

* Let me put in preference categories of food, and after planning a route, look for restaurants near where we'll be at breakfast, lunch, and dinner. Double-plus bonus: Only recommend restaurants that are open at the time I'll be there. (Yes, Google does have a first approximation of this information, though it's often spotty.)

* Let me (easily!) blacklist specific businesses or chains. I hate calling up a map with that shows 15 restaurants in an area, and where I would only ever go to 2 of them, and having to click on all the dots until I find the right ones. Google Maps needs this feature!

* Let me filter attractions that get terrible reviews, so they don't clutter up my map -- and pull in reviews from Google AND TripAdvisor (assuming they let you?) and other sites. In some small towns, you might have one review on Google and one more on TripAdvisor -- if there are a ton on both it doesn't matter, but if there are only a few, even one more can be relevant.

Is this a good business plan? Heck if I know. I only know that I really want a site that does all of this right now (or at least points 1-3). And I sure-as-heck would remember a site like that and find it again when I took my next road trip. Bookmarks are magic ways to supplement your memory. No idea how many people still do road trips, though. Maybe more would if they had the right tools, and knew what awesome pla...

I also wanted a map with both Airbnb and hotels, so I made one myself. It's now an aggregator that includes all the hotel sites and a bunch of airbnb's competitors too. The site is http://AllTheRooms.com.
I do like your site but for everyone designing these sites: Please add an option for children. I use services like this very often but I'll skip it immediatly if there is no selection for children (you can guess why).

edit: There is even a bigger problem with your site, the prices do not match even close, see "kotimaailma" - the actual price is not even close to the price you display.

http://imgur.com/z1Zniof

http://imgur.com/erTmv4p

edit2: Or is the price per night? Not the whole stay?

I'm not saying his site does this, but some of them misleadingly display prices pre-taxes, which for hotels in the US can be up to 20% less than you end up paying.
We try to show the same price as the site we're linking you off to. The common practice of 99% of the sites out there is to include the taxes in the price for non-USA destinations, but for USA destinations the taxes are added later. Of course it's ridiculous and doesn't make sense, but the logic is that since everyone else does it that way, you have to as well or it looks like your prices are worse than everyone else's.

There's also the question of fees, and we haven't handled that as well as we need to. For example, Airbnb adds fees on during checkout that aren't included in their landing pages. When we include those fees, which we do right now, it looks like our prices are too high. But we keep them there anyway so that there is a fair comparison with other accommodations options.

Price is per night. I guess we need to message that better!
I agree - everything in the travel space is crap. Whether it's because it's hard to monetize, or because there's no archetypal traveler making it hard to cater to any particular audience ... I don't know. It's a tough nut to crack.

It's not going to help you plan but if you'd like to blog about your road trip when you're on the road, take a look at my attempt to build a "micro blogging" website. Each day, you're only allowed to write 250 characters and attach a single photo:

http://www.trott.in/

It's free to use, feedback welcome. I wrote the site for my little road trip because I was so unhappy with everything else out there. The idea being that a character and photo limit forced you to be concise (much appreciated by friends and family), making it easier to maintain and look back on. Here's our trip (we were lucky enough to get some air time on the BBC world news):

http://www.trott.in/trips/unomas-all-the-way-down

Hey mate,

just signed up, i'll give it a shot for my upcoming trip, few points from the sign up process:

- Dates seem to be American Format (this is fine but at least indicate it in the placeholder text) - I have no idea what a marker is, perhaps explain it or even let people know it can be blank!

My first reaction was "that's not enough!", but on further consideration...

I'm going to sign up and give it a try. Thanks!

> This is for the MVP, and shouldn't take a competent developer more than a week working with Google APIs or equivalent. A good developer should be able to crank this out in a day or two. I'm tempted just so I can use the functionality to plan my trip!

I assume you're not a developer?

Yeah he wants a geographical recommendation system with tons of data that likely don't even exist online like restaurant menus, and have that quickly hacked in a week.
I'm not looking for anything that isn't online already. I would be happy with JUST the results available in Google Maps, in fact.

I'm not asking for restaurant menus; the restaurants ARE categorized in Google Maps already.

I know exactly what data is available, and how I'd code it. I just don't have the time.

(comment deleted)
I'm surprised recognizing an animal in a photo is his example. Apparently computers are already almost as accurate as people. https://karpathy.github.io/2014/09/02/what-i-learned-from-co...
Yeah, and it only took like 50 years. Easy. Next problem?
And location data in the photo only required relativity and space travel.
Hey, shorter than it took evolution.
Good point. I'd be curious about the person-hours worked on both the problems in the comic.

My first reaction was "you'd have to explain some things are easy cause there's libraries/tech that does that". I guess the real explanation is " countless hours and dollars spent by others who came before us make this easy...".

No, I'm an awesome developer. But I mostly do games, video streaming, and app development, so I don't know the relevant Web APIs.

Would probably take me 3-4 solid days to get to MVP, maybe even the full first week, given that I'd be slowed down by the learning curve. But I'm also very busy (see: "I'm an awesome developer").

Action speaks louder than words
And your action is to downvote the truth because I haven't spent 40-60 hours proving that I am an awesome developer? Sorry, I don't feel the need to prove anything to you or anyone I'm not currently interviewing with. My resume speaks for itself.

It's also about five hours of work to just do it the boring way by hand. An 8-12 year amortization of a project that people have argued eloquently is a total waste of time as a start-up? Why wouldn't I work on something I cared more about, instead?

Hey Tim,

So what did you end up doing for your roadtrip? Did you find a tool or did you just do it on your own? I'd be curious to see what you ended up using.

Thanks

You could just get a guidebook, lonely planet or whatever. They usually have maps, tips on places to visit, restaurants, ... and best of all work without internet connection.
Guidebooks remain surprisingly useful for a lot of circumstances. They're far from perfect and tend to be out of date for food/lodging but they're still a well-organized and inexpensive resource that at least provides a solid starting point.
I could, but considering the length of my road trip, I'd probably need nearly a dozen, if they're done by state (more if some cover only a portion of a state): My trip will cover: Colorado->Kansas->Missouri->Arkansas->Alabama->Georgia->Florida->Mississippi->Louisiana->Texas->New Mexico->Colorado

I don't want a library of guide books to be taking up space in the trunk.

Amazon.com has an electronic book reader that will knock your socks off.
Agreed. I don't take vacations, so I wouldn't know about travel planning, but when I buy plane tickets (which isn't very often) I always use the same service. That used to be Kayak, but I changed it to Google Flights a year ago because their UI/X is way more simple and more intuitive than anything else out there (AFAIK).

So I too don't think the seasonal argument holds up, it's just about quality and marketing.

Even the ones with a lot of effort put into them suck for the same reason project/task/todo management software sucks. Everyone plans things with a different thought process.
This exists, just not as a web app- your local AAA will gladly map out a road trip for you complete with the locations of gas stations and attractions along the way.
Triple-A does a lousy job of planning out road trips.

My girlfriend insisted for years on how great Triple-A was and wouldn't take any of my suggested routes (I live for road trips, I've driven all over North America). Triple-A routed her from South Dakota to North Carolina via every toll-road and congested interstate there was (Chicago, Toledo, Cleveland, Pittsburgh). I said drive down to St. Louis and enjoy a toll-free drive through the Kentucky and West Virginian countryside. She went with Triple-A's route on the way out and spent who knows how much money on tolls just to sit in Chicago's traffic. Took my route back and got a beautiful ride through Appalachians in the fall.

Loved this post - for any others here who share similar views, thought I'd share a few thoughts from our experience working on this.

I'm co-founder at https://www.wanderant.com. We started off with similar frustrations on planning trips. All the information you could ever want is online - and for free - so we should better off than where we were when you'd just buy a Lonely Planet book. But that's not the case, I think it's actually gotten harder - partly because there's so much info, and so many options.

We're a year+ into it, and have been iterating multiple times on an MVP. It's a big problem to solve, so 'minimal' is a bit high - plus it's a different minimal for every traveler you meet (e.g. comment here on "an option for children" which is absolutely critical for some).

Here are some things we've learned along the way:

* Top 3 things people need / want that haven't been solved:

- Local expertise - esp when traveling abroad - what is the local yelp / gothamist / etc? - Help with logistics - mostly around how to get from A to B - Rome2Rio is a great help in that regard, still takes a lot of work for planning an entire trip though - A way to manage a plan in one place - instead of email /bookmarks / excel

* Some of the challenges we've encountered:

a- Making a product that's easy to use - If you're only solving one step (e.g., online booking), it's easier to create a workflow that makes sense. I love examples like how hipmunk have simplified UX for booking flights. We are building towards a workflow that lets you keep your entire plan in one place - ideas, map, notes, reservations,... and finding a UX to make that easy is a lot of work.

b- Getting to a product that really adds value to planning- We want a tool that simplifies the process of planning. However, we clearly can't start with a product that does everything you need for a trip. Even in the near future, our product will continue to be an incomplete solution. So paradoxically, by being an additive tool in the process, we've successfully worked against making it simpler :) We have to make up for that by really adding a lot of value and saving time fr the user- and getting to that point is also a lot of work

c- Marketing is hard - others have mentioned the challenge of facing giants in the space- I'd like to offer another piece- which is reaching trip planners at the right time. Only a small % of people we reach are in the process of planning a trip. Then if they are, we most likely don't yet offer very rich content for where they're going - because currently our higher-quality content is still nascent. So that makes finding the right users hard. Any help here is appreciated btw - if you know someone who could use this send them along :)

* Why we're continuing - Times like this, when we see someone get passionate about how much they wish this existed or how they can't believe it hasn't been done before. We feel the same :)

- While it's a hard problem to solve, and there's a lot of challenges we already know of and more we don't yet - it is a really interesting problem to think about and try to crack.

- More than all, we love to travel to new places and explore the world. If we can share that experience and make it easier for a few others, we'd be ever so pleased.

As someone who travels a lot, I like your top three things, especially the first. Though taken alone that starts looking a lot like a directory of directories. One problem, as you say, is that there's a lot of information out there but it's uncurated and often based on specific commercial interests.

I just discovered Rome2Rio on this thread and it seems useful for things like whether I can take a train from A to B or whether flying makes more sense.

I use Tripit for much of my organization but it obviously only captures some things and it's format for displaying a whole trip is moderately awful.

Just glanced at it briefly. Looks almost entirely unlike what I need. :(

"26 cities available for the United States" ? I'm not visiting some big famous city by air; I'm going on a road trip. Looking at the list, I'm going to be at two of them, but I'm also going to travel through New Orleans, Kansas City, Springfield, MO, Memphis, TN, and about 100 smaller towns on the way. The point isn't to get to (e.g.) Orlando ASAP, it's to have fun on the way.

Regardless, if I have to list each town individually, the site is almost worthless, because I can instead just Google the destinations myself. It looks like I can accumulate lists of destinations IN a town, but for anyone who's traveling by car, a travel site that only shows the most famous attractions in a small number of big cities is doing no one a favor.

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Hi Folks..

Have been a dormant user of Ycombinator for some time. I have been researching on this topic for the last 4-5 years. To be really honest I think TripHobo.com does not fit SomeCallMeTim's use case. I think Roadtrippers.com may fit the bill. Having said that, I am a big fan of TripHobo.com. I have seen the portal evolve for sometime and I see it as the closest solution to fixing travel planning I have my reasons here: 1) The only source which gives you draft itineraries created by other users. This is immensely useful as i can see what other are planning to my destination. I planned a trip to Rome using TripHobo.com and i find it immensely useful.. 2) If you hit Plan my trip button, the TripPlanning functionality is awesome. You can add almost all attractions in a city to your trip plan and you can hit the optimize button, you get an automated route planned. What TripHobo claims is that the route plans generated are not only optimized for distance but also for opening and closing times of attractions. I think this is really cool. No one does it so easily.. not even google! 3) The ease of usage: This is the most easy to use portal for trip planning.

Limitations: I think there is only one limitation as SomeCallMeTim pointed out.. Limited number of cities .. I counted the number of cities manually in August last year, i could find 171 cities to which i could plan trips to. I counted again on 5th october 2014 and i found that there were 243 cities. Today i saw that they have changed their interface to a search bar and hence I am not able to determine how many cities are enabled on Triphobo.com.. If they go on increasing the number of cities to which one can plan his/her trip to say 3000-4000 cities around the world.. i think TripHobo.com will have fixed travel planning for sure. My 2 cents!

I am also tracking folks like roadtrippers, mygola and tripomatic. To me these (along with TripHobo) are the leading 4 travel planning players today. MyGola has been a disappointment..Tripomatic is difficult to use..Roadtrippers and TripHobo are i think getting some serious traction .. Roadtrippers has primary focus on roadtrips whereas TripHobo is a holistic leisure travel solution if they are able to scale their content..

Hi there, I'd love to hear why you think that Tripomatic is difficult to use. If you don't want to write it here, could you get in touch with me at barbora@tripomatic.com? Thanks a lot!
But is the problem that the world doesn't have a good road-trip-planning app, or that the world doesn't take enough road trips to warrant such an app? That's more of Garry's point, at least as I interpreted it. Lots of people have travel-planning needs at the moment they're planning travel. Unfortunately, most people don't travel all that often.

How often do you take road trips like this one? More than once a year? Monthly? Weekly? If you can convince me that there is a large addressable market full of people who take weekly or monthly road trips, I'll grant you that someone needs to spend some cycles making a better road trip app.

Now, this isn't to say that it's not a real problem. Clearly it is. Case in point: you're taking a road trip, and the apps you've looked through suck. You'd love something better. As would others. Fair. So perhaps the ideal solution here is for someone to make a better road trip planning app on the side, as a hobby. It's probably not a big enough market to warrant a startup. The use case is too specific and too infrequent to build a viable, fast-growing business model around.

No disagreement here. I ended with a question as to whether there's a market; I don't know that there is.

AAA apparently has a road trip planner that's only available to members. That's one business model. :)

TripAdvisor could offer something to help promote their site. As I said above, a strong developer could crank out something better than most existing alternatives with a small time commitment.

A hobby app might be the right speed. Some suggestions I got above might end up being "good enough", though.

I don't think you can solve this with just APIs currently. There's a ton of information currently but extracting the useful bits and creating a complete trip plan just isn't possible today.

Heck I've done the equivalent of screen scraping by visiting tripadvisor and lonely planet thorntree forums and even that was not enough. I tried a new site called triptips.com and found they had good balance of human intervention from locals to simplify the hardest part of travel planning.

Its relatively easy to book a flight or hotel or air bnb. The hard part I've always found is determining which hotel makes sense given what i want to do at the destination. should i rent a car and so on..

I believe this is one of those things where everyone has their own idea of what 1 - 3 should be. I think it's ambiguous enough that people will see what they want to see and then realize that the vision doesn't match when actually implemented.

A trend that I've noticed is that many people don't put much effort in trip planning. Their workflow is basically read travel blogs, talk to friends, pick a couple of big points of interest, book a place that seems nearby to some things, and rely on mobile internet/concierge/locals for everything else. And maybe aside from finding the best place to stay, I haven't seen people consider the other steps to be pain points.

Tripit looks to have had a reasonable exit before this article was written:

http://www.crunchbase.com/organization/tripit

http://www.crunchbase.com/acquisition/0551c63d066e0afe86046a...

TripIt isn't a planning site, it's more of an organizational tool.
Correct. Once you're done planning your trip, you can send it to TripIt (or give TripIt OAuth access to your email) and it'll be organized in your account. There is no planning.
I have two primary concerns when booking a travel, one that I don't end up at a boring place and two that I can manage it in the most economical way. Google search helps me figure that out pretty well. Google Maps are great when I'm actuall at that location. TripAdvisor has nice information. Airticket listing sites are a necessity. AirBnb works well for places to stay. Lot of hostel booking sites in Europe work well. But I haven't found one single tool that can handle all that exhaustively.

Way too many travel planning softwares try aggregating resources from across the internet, just posting it in varied forms. But they don't really give me the confidence that it's the cheapest and the best place I can be at. Moreover, when you look carefully at them, they skimp the details -- the prices and timings are usually way off. To top, if they try to put a fees on top of the original price, it adds to the cost without actually providing any ease. So I still have to resort to going to the original source of the content or just doing my own research. Also, many of the travel planning softwares overlook the fact that motivating people to go for a new trip is a huge challenge. It's also interesting to note that the blogpost was written over 2 years ago and is still true.

"cheapest and the best place I can be at" -- that phrase is entirely too subjective to be able to actually easily solve. I know for myself, say on the Big Island of Hawaii (a place I know pretty well), "best place" can incorporate temporal concerns, desire for beaches or mountains/hiking, maybe a place with a kitchen vs. sustaining one's self on market goods and restaurants. Those three variables could describe at least four different places on the island in my own mind. How does that get mapped to a general site?
Exactly! Every person has his own concerns about planning a trip and the problem is too subjective. That's why I said, I have to resort to my own research to figure out the place, instead of depending on a travel planning app. Travelogues and ratings posted on blogs and TripAdvisor give me a better idea of what to do, compared to a list of things generated by an App.
A question I'd love to have answered - I want a flight that is within min/max miles and costs less than a certain point intersected with a certain class of lodging within a certain price range. Available "amenities" of the location a gravy filter.
I wanted a site that gave me the confidence I was looking at all the places to stay in a destination, including the actual prices from every site. Nobody was combining airbnb with hotels and Hotwire and all the other sites I checked. I ended up building it myself: http://AllTheRooms.com.
No one remembers Dopplr? It was a pretty popular social travel planning site before Nokia bought them and froze it to death. It was like, one of the original web 2.0 sites alongside Flickr.
I had the feeling no one used Dopplr for vacations. Me and quite a few people I know input their conference and business trips, so with only a bit more traction it could have served "oh, you're also in $CITY, let's meet" quite well.

This was in Germany and a few years ago, though. With only tech people. Not a bad demographic, but there's probably a reason it got canned.

Dopplr went after the conference/business market, and at least in my crowd it had critical mass. That might be because I know the founders...

But it cracked OP's issue of needing daily use so you remember the service. I would check Dopplr to see which of my friends were coming to London -- that's much more frequent than me travelling, to the tune of travel_frequency * friends / cities. It was useful, and I still miss Dopplr today.

I was the founder of TouristEye, a travel guide app that makes trip planning really easy. We got into 500Startups, we reached 500k registered travelers and then we sold the company to Lonely Planet, the leader of the sector.

I see myself on this post. Several years ago we decided to build an amazing trip planning, that allowed you to plan your trip day-by-day. You can see some screenshots on the Chrome extension (https://chrome.google.com/webstore/detail/touristeye-planner...) (not working now). We got over 100k users using it on their trips (not daily users obviously). It was gorgeous, people really loved it, Google really loved it, but the usage was pretty low. Just 5% of our users used it.

So because we were a startup we decided to kill it and we focused on capturing user wishes, and recommending those things for their trips (kind of Google Now for trips and offline). That's what gave us more usage, more income and finally it was one of the reasons of our exit.

So, yes. Trip planning sucks as a business. But all our team remembers it proudly. It was just fucking amazing :)

Ah man, I've been working on http://sploria.com/ for a while, leading up to launching an MVP soon and hadn't heard of TourstEye. Had a look at the app and the 'experiences' part is almost exactly what we've been building, damn :(

Congrats on your success with the product though, it's really beautiful!

Everyone seems to have a different understanding of what a "travel planner" is / should do. I was thinking of rome2rio when I read this headline (which is very nice and doing great apparently), but from the comments here I gather many people want to solve the "social" (i.e. what to see etc.) aspect rather than the pure technical one (how to get there, how to save money) of it.

Considering how much money goes into travel (and related mergers/acquisitions - these are real acquisitions and not inflated valuations from 7-8 figure investments), it's definitely not a bad idea though.

I discovered http://www.rome2rio.com a few months back and it's a fantastic site. This is what I was expecting too, it will give me all travel options from point A to B, Google Maps but international/cross border. Maybe something changed on that Yahoo Travel planner, the original article was posted over 2 years ago.
The other bad idea, local travel experiences, there were hundreds of them, but it's really hard to get critical mass, because you need to have enough experience hosts, experiences and then also visitors. The only ones that made it work were www.getyourguide.com who raised $14M.
I think its the classic chicken-egg problem like any other platform.
It feels like the author likes to see his family suffer and fundamentally misunderstands reality:

> everyone has the problem of not spending enough quality time with friends and family. Travel is the best and most meaningful way to do that.

Travel is an acceptable means to making it possible to achieve the end goal of spending time with friends and family, especially when separated by great distances. However as a means of directly spending time with one another travel is the most time-consuming and stressful way to do that; especially when you mix the ambiguity of squishy human sentiments with a rigid travel schedule.

And this is probably why nobody really gives a damn to use such things.

This is a lifestyle question and these are hard to generalize. It works well for me personally. 3-4 days someplace doing sightseeing, or maybe some outdoor activity is an accessible way of spending a few days with someone and having time that we wouldn't otherwise have. Many of my friends and family live in a different country. Flights and accommodation are affordable. Time is scarce and if we visit eachother in one of our normal lives, it's harder to find whole days to relax hang out.

A context for spending time together is (to generalize) a pretty good way of maintaining relationships, relaxing and having fun. You might have a friend, parent or child with whom you occasionally go fishing, hunting, bird spotting or whatnot. You might have an old army friend you meet every few years for something else. You might have a cousin you meet for a run once a week. Whatever the specifics, context for spending time together between people works in many cases.

Travel is a good context. It's accessible, easy to arrange and works for a lot of people you might want to catch up with.

This fits perfectly with my startup food-chain theory.

In the internet startup world, there is an invisible food chain, whatever "higher" models will eventually "eat" "lower" models.

A travel planner, with low frequency, no real pain, doesn't stand very high on the food chain.

I'm curious about your food-chain idea. Can you explain it a little more and give more examples?