Travel planning software: The most common bad startup idea (2012)

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.<p>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 (<a href="https://chrome.google.com/webstore/detail/touristeye-planner/kpjpejalhlnocbhggpnokneghfenoneg" rel="nofollow">https:&#x2F;&#x2F;chrome.google.com&#x2F;webstore&#x2F;detail&#x2F;touristeye-planner...</a>) (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.<p>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&#x27;s what gave us more usage, more income and finally it was one of the reasons of our exit.<p>So, yes. Trip planning sucks as a business. But all our team remembers it proudly. It was just fucking amazing :)

The problem with travel planning isn&#x27;t frequency of use: as other people have pointed out, Zillow and Cars.com are used infrequently but make money.<p>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&#x27;re reluctant to do so.<p>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.

<i>How often do people really plan trips? For the typical working adult, probably once or twice a year if you&#x27;re lucky.</i><p>This is exactly why this doesn&#x27;t work. There are tons of things that people do that need fixing, but they do them so rarely that the costs of adopting the new way of doing it are significant when compared to the cost of just doing it the old way.<p>Said another way, very few people are going to take an hour to learn a new process which would otherwise only take two hours a year to do.<p>edit: This also is a way that a start-up could go super wrong and not know it until they try to scale. Identified pain point, good solution, engaged users with a real problem use it once and then it drops off completely. Talk about frustrating!

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:<p>- Incentivize employees who share rides from&#x2F;to hotel&#x2F;airport traveling on same dates&#x2F;destinations<p>- Show dates for destination that maximizes networking opportunities (in between conferences)<p>- Show locations with wifi in-between meetings<p>- Locations with ambiance ideal for business discussions<p>- Expense capture to identify opportunities for deals (employees love Starbucks during business trips, sign up for corporate deals)<p>For those solving these sorts of problems, you might wanna to check this out - <a href="https://developer.concur.com/devcon/PerfectTripFundAwards" rel="nofollow">https:&#x2F;&#x2F;developer.concur.com&#x2F;devcon&#x2F;PerfectTripFundAwards</a>

Please can someone answer the following question, in all seriousness:<p>What problem is the travel planning software startup solving?<p>Never have I planned a holiday and thought &quot;I need an app for this.&quot; Maybe a better flight booking system, or a better guidebook, but never a website or app. In fact, I find planning holidays enjoyable and fairly straightforward.<p>I know of no-one who has difficulty planning their holiday, beyond the flight problem. And to make this work, you&#x27;re going to need a lot of people with the same problem, whatever that problem is.<p>Anyone?

If only we had some combination of software and people with expertise in destinations. Maybe we&#x27;d call it a travel agent or something like that.<p>That was snarky. But it points to the historical problem here. Most travel agents didn&#x27;t&#x2F;don&#x27;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&#x27;m guessing can&#x27;t be easily codified in software.<p>In fact, I&#x27;m sure there are plenty of competent travel planners but they cost money--i.e. are luxury goods--and most people don&#x27;t want to pay the money.

The opportunity in travel these days is targeting people new to travel. Forget North America. Target young Chinese travellers who are just now beginning to learn there&#x27;s a way to travel without staying in hotels and doing bus tours from highlight to highlight. Or wealthy Russians. You have to go really niche if you want to make money.<p>25 years ago when companies like G Adventures, Intrepid etc. started, nobody knew about small group travel, mingling with locals etc. Now that&#x27;s all the rage for westerners. Bring that idea to markets that are new travel and you&#x27;ve got some opportunity.

We started <a href="http://www.voyando.com" rel="nofollow">http:&#x2F;&#x2F;www.voyando.com</a> in March this year. It&#x27;s basically a crowd sourced travel advice platform (a travel planning site in a sense). You&#x27;re paying others to hash out your plans with your specifics (hours of travel, accommodation, proximity of restaurants, etc etc).<p>We are guaranteeing 3 good proposals for your trip and the best will receive the specified reward (anything from 5-100 dollars).<p>The struggle we are facing is that we are unable to get a decent amount of traffic because of the really big competitors with deep pockets to acquire this traffic. We&#x27;re not in the same &#x27;idea space&#x27; but we are still in the travel segment. This makes it incredibly hard to compete.<p>Despite good press, really good customer satisfaction and a business model, the site is struggling. We are now looking to partner up with one of the big brands to &#x27;catch&#x27; drop offs from their main site with a service that can retain the customer. Maybe I&#x27;m being to optimistic that any big brand will take this chance, but I&#x27;m confident that our platform does it job and that it can be a tool to get your drop off rate down (&quot;Didn&#x27;t find what you were looking for? Let our experts help!)<p>If anyone can hook me up with the right people to pursue this, I would be very grateful :-).

This is a great observation! I&#x27;m two months into this &quot;digital nomad&quot; experiment, and the biggest pain has been lack of central organization for my schedule, todos, costs, sights-to-see, etc.<p>My interpretation is that the domain is simply too big, and the field of &quot;personas&quot; so varied that finding a critical mass of core users around common use cases is nigh impossible. Even within those identifying as &quot;digital nomads&quot;, you have adventure tourists, travel-blog content marketers, $100&#x2F;hr front-end consultants, cultural commentators, resilience quacks, and so on.<p>Look at a site like TripAdvisor, which does a great job of aggregating the <i>most basic</i> reviews of restaurants, hotels, etc., and even it contends with enormous problems like data rot, internalization, etc.<p>I suspect that, if the &quot;long-term travel&quot; 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 &quot;apps for digital nomads&quot; is something like a nightmarish goose chase through an illegible jungle of travel blog shills.

Sounds clever, but it really doesn&#x27;t stand up to scrutiny. There are countless profitable businesses that aren&#x27;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)<p>Travel planning software is difficult because there&#x27;s so much competition and a lot of political forces trying to keep the newcomers out.

Everyone seems to have a different understanding of what a &quot;travel planner&quot; is &#x2F; 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 &quot;social&quot; (i.e. what to see etc.) aspect rather than the pure technical one (how to get there, how to save money) of it.<p>Considering how much money goes into travel (and related mergers&#x2F;acquisitions - these are real acquisitions and not inflated valuations from 7-8 figure investments), it&#x27;s definitely not a bad idea though.

Kind of surprised that the OP hadn&#x27;t mentioned Hopper, the travel startup that was founded in 2007, promised to bring &quot;big data&quot; to travel discovery, and still hasn&#x27;t much to show for $22M in venture funding: <a href="http://techcrunch.com/2014/01/20/why-travel-startup-hopper-founded-in-2007-took-so-long-to-launch/" rel="nofollow">http:&#x2F;&#x2F;techcrunch.com&#x2F;2014&#x2F;01&#x2F;20&#x2F;why-travel-startup-hopper-f...</a><p>But I agree with the OP. Travel planning is a rare luxury, even for the rich. And I don&#x27;t know what it&#x27;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&#x27;s not really a travel service that can meet the needs of wanderlust.

AirBnB is a solid exception to the &quot;must be daily users - 20% retention&quot; statistic. No way is their average user base a daily user.

It&#x27;s a bit different when it comes to business travel. I&#x27;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&#x27;t want to stay in crappy places. I&#x27;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.

Having thought about this idea in the past, I can say that one of the difficulty lies in the fact that the market &quot;seems&quot; 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 &quot;trip&quot;, 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 &quot;love&quot; your product. So rather than daily usage, I think the problem is of segmentation first (and competition, etc following...).

I think the issue is revenue and not user forgetting about the website. People remember sites years later. The problem is the business model. People are not willing to pay for the services of a travel planner which is expensive to build, which means your revenues are affiliate or ad based. This is not enough to support the dev costs.<p>I&#x27;ve just read many comments that show getting traffic is not an issue. Yes it might be more competitive but lots have gotten traffic. The common issue I see is that none of them have been able to generate enough revenues to support themselves, even with good traffic.

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&#x27;t work. &#x2F;S

I think a lot of travel sites focus on saving money for travellers. What if money is not that important.<p>My friend came up with this idea. I think it will help many people. The idea is that one put in how much they want to spend and how much time they have. The site will show various travel or activity options that are possible. One can further limit by parameters such as road trip only, out of state destinations, in town activities, etc. Almost like travel agents.<p>I have been looking for something similar but haven&#x27;t found it. My friend is a great traveller and he and his wife have run out of places to visit. They just want to explore new places.<p>On other hand, my wife &amp; I are not so great travellers, we never know where to go. We end up picking top destinations from TripAdvisor, then we find those a bit too expensive or require too much travel time, etc. Sometimes we just want to get out of town and not worry about where we are going.<p>For now, I have solved this problem for us by creating a spreadsheet, with a list of places we had picked and estimate cost, best travel time, and ideal # of days to spend there. But of course, this is for places we researched and could not afford at the time.

This article rings very true, but on the other hand I&#x27;ve thoguht the same thing about a dozen other things that seemed dead until someone came along and did what seemed impossible.<p>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 <i>almost</i> completely right.

Figure I&#x27;d add my own two cents to building software for this: School project with a few buddies, decided to make an itinerary planner. Problem was that it was messy and difficult to plan a trip with 3+ people. Emailing back and forth gave you long chains, calls and group chats were difficult to schedule together and settle on something. Ultimately a Google spreadsheet or shared doc was the best option despite limitations. Enter the itinerary planner: Post possible destinations, majority vote by a certain time to include or exclude in plan. It was to act as a central place to plan pre-trip, view during trip, and post after trip(web app or native app).<p>Eventually, the realization was the same problem as most people have mentioned, retention. So then comes the weekend planner. Miniature trips or adventures for weekends or long weekends are much more common, spontaneous and way easier to make decisions. Google Now already offers suggestions of events and places to be during the weekend based off Geo and whatnot, just have to take it a step further.

I had a travel planning startup for 5 years and I agree 100% with Tan&#x27;s about that you have to re-acquire the user every 9 months and the main reason is that the user is unable to remember your &quot;name&quot;. But imho the main problem on travel industry if you are doing a travel planner is not exactly that the user doesn&#x27;t remember you... this happens at other industries: job finders, real state, consumer electronics...<p>The big problem in travel is competence. It makes user (re) acquisition REALLY expensive and probably, as a startup, you can&#x27;t afford it (an this mixed with no actual retention is painful). And why is it so expensive: because you cant compete with advertising, SEM or even SEO with big players out there with a LTV that multiplies yours by 10x. And actually, do a better job than you when we are talking about user satisfaction.<p>Airlines, big online travel agencies are really good at this and pay for a) Long tail SEM, b) content for being top SEO. Remember, Online Travel Agencies are technology companies with big resources. They are extremely good at SEO, at loyalty, at landing page optimization, at design, at customer service... their life is on it.<p>Think about this scenario:<p>User searches at google for &quot;traveling to Vienna&quot; (or even &quot;travel planning vienna&quot;). You know two things about that user: 1) He wants to plan his trip to Vienna (75% true) 2) He is going to buy cheap tickets to Vienna (95% true).<p>Big OTAs or Airlines know this, and what they do? They fake they are travel planners doing better (expensive) SEO than you as they know that user is going to buy the ticket at their site (that&#x27;s 2$ per visit revenue)... because they do that extremely good. If they fail noone cares: User wont remember and at least they had brand awareness for their plane tickets.<p>Anyway, i think the problem is much simpler and applies at every industry: if you don&#x27;t have a great retention (and this can be something not under your control, e.g. because what you are selling is needed twice a year) you have to be really good at user acquisition. And being good at user acquisition at a not-niche sector is extremely hard, no matter how good your product is. Probably you will have to focus first on what&#x27;s your hack on getting users instead of at having a good product. Sad but true.<p>I&#x27;ve been reviewing Alexa&#x27;s top travel sites for years hoping something changes... and its pretty discouraging: only 1 of top 25 sites not a ticket-seller: Tripadvisor (2nd). 4 in top 50, and all of them are super seo sites.<p>Google has been punishing not content sites for years, even being the best solutions. We&#x27;ve seen a lot of amazing ajax tools for almost every problem we could figure out... but if they were not seo compatible, everyone forgets them. I hope this changes in the future, e.g. mobile apps have another search scenario.

Frequency of need is a non-issue in the travel space or any other. As has been pointed out, there are many other spaces where lack of frequent visits has not been a barrier to success. Nor is name recall&#x2F;retention an issue - if you create a great first impression i.e. delight your customer the first time and give them something they really like, they are unlikely to ever forget you.<p>IMO, the key issues to cracking this space (and these are beyond building a great product that people will find useful which is crazy hard anyway!):<p>1. Getting new users from free channels&#x2F;biz dev 2. Getting new users from free channels&#x2F;biz dev 3. Getting new users from free channels&#x2F;biz dev<p>Most startups look at user acquisition as a secondary consideration to the product. In the travel space, it has to be atleast an equal priority, if not an even higher one. You HAVE TO figure out how to hack user acquisition from free (or very cost effective) channels or you will fail. The sooner you start thinking about that the better.<p>4. Making money. If you can acquire millions of users, this becomes significantly easier.<p>5. Breadth&#x2F;size of the space. This is a huge space with tons of variables and different personas. You have to figure out a way to make this work to your advantage. For example, most travel startups, being based in the US, seem to think that users only exist in the US. There are millions of users, especially in fast growing developing countries, who are pretty much being ignored. Another example - if you can figure out how to service the whole space well (and I know thats a BIG if), then at any given time you are going to be catering to some kind of user (increasing your likelihood of reaching millions) unlike a niche service that requires to scale based on a very specific user persona<p>If you can keep acquiring new users cost effectively and delighting them with your product, you will succeed in the travel space. Most startups cant do this and thats why they fail. they dont fail because of the frequency of need or name recall.

As someone who is working on this idea currently, this post has really got me down.

Why not target travel agencies instead? Agencies can create&#x2F;manage itineraries, hotel reservation &amp; bookings, destination maps, etc? This will get you paying customers and daily users.

I have two primary concerns when booking a travel, one that I don&#x27;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&#x27;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&#x27;t found one single tool that can handle all that exhaustively.<p>Way too many travel planning softwares try aggregating resources from across the internet, just posting it in varied forms. But they don&#x27;t really give me the confidence that it&#x27;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&#x27;s also interesting to note that the blogpost was written over 2 years ago and is still true.

Creating travel planning software may well be a bad idea, but I find the reason he gives is really weak. It boils down to:<p>People in America don&#x27;t plan travel often enough.<p>If that was the reason, then almost any travel startup is non-worthy. This is definitely a problem, but it&#x27;s more to do with the difficulty of ranking a travel planning site in Google which is where people who don&#x27;t travel often usually begin their planning. This is why SEO is so critical to any travel website.<p>It also conveniently ignores the rest of the world as a market. People outside the US do in fact travel far more often and more elaborately and ignoring them in the equation just boggles my mind.<p>Disclosure: I&#x27;m also one of these people who acted on this bad idea of creating a travel planner: <a href="http://www.travellerspoint.com/planner/" rel="nofollow">http:&#x2F;&#x2F;www.travellerspoint.com&#x2F;planner&#x2F;</a><p>My experience from this is that people do have very different expectations of how a travel planning tool should work. So the earlier comment that it faces the same challenges as to-do apps, etc.. rings very true to me.

The biggest problem I have had with travel planning startups is that many of them focus too much and too quickly on monetisation - often leading to a poor user experience.<p>When I&#x27;m travel planning, I like to somewhat explore the destination (like reading a guide book) and think about what to do, where to stay etc -- rather than being immediately shown a list of hotels &amp; airfares.

I&#x27;m aware of one such startup (<a href="https://roadtrippers.com/" rel="nofollow">https:&#x2F;&#x2F;roadtrippers.com&#x2F;</a>) that has $4 mil in funding[0]. Ideas don&#x27;t work until they do, I think this nut can be cracked.<p>[0]<a href="http://www.crunchbase.com/organization/roadtrippers" rel="nofollow">http:&#x2F;&#x2F;www.crunchbase.com&#x2F;organization&#x2F;roadtrippers</a>

The big problem I see is that planning does in a lot of ways remove the essence of travelling (see The Art Of Travel by Alain De Botton). The best trips I&#x27;ve been on have been largely unplanned and taken on a day to day basis which flies in the face of a single up front plan which is built once and referred to throughout the trip.<p>What I do see a market for are the tools which sit in the middle and enhance your ability to plan once your in a location. Tools like:<p>- flight management - hotel booking management - local knowledge resources - tools for connecting with locals - language tools<p>A lot of these are already available in various forms through dedicated applications. I use kayak, hostel bookers, app in the air, wiki travel plus local subway and language apps. Whether there could be an advantage to it all being in one place I&#x27;m not sure but the tools on their own seem to do pretty well once you&#x27;ve put together your toolset.

People don&#x27;t buy cars or get married very often either, but there are plenty of tools to help with those processes.

I&#x27;ve been working on a travel activities startup in stealth mode, but had to put it on hold because of other work.<p>Reading this article made me think back to some of the challenges I had initially with customer development. People were always interested in the idea, but everyone seemed to want to use it differently. It was a real challenge to come up with something that would be useful and satisfying for most customers.<p>Along the way, some people tried to talk me out of it, saying that the app should be more like location exploration, because people don&#x27;t travel alot. My response was that while everyone doesn&#x27;t travel often, there is always someone who is planning a trip. I don&#x27;t think the frequency of travel is the issue--it&#x27;s the logistics of it.<p>Enough of waxing nostalgic, I think I&#x27;ll get my packages and libraries up-to-date and get back moving on my idea.

I can see why travel planning startups fail but I don&#x27;t think its for the reason implied that people don&#x27;t want the service. I travel a lot and I always plan (to an extent) on line but I go to the best sites for the aspect required eg. for flights Skyscanner or Kayak, for accom booking.com or laterooms or hostelworld or airbnb. For what to see Tripadvisor. If I want combined hotel and flight, Expedia. For local bus times etc. Google Maps. They are mostly great services from billion dollar companies that have put in a lot of R&amp;D. Why should I go to a new combined travel site trying to combine stuff in a half arsed way? To appeal to users it has to better than the existing solutions already available.

I have a travel startup that is meant to solve the planning problem in a different way, but I agree with Gary. We painfully learned that -<p>a) We created an elegant solution to free. That is always a bad idea<p>b) User acquisition is extremely hard without spending tons of money<p>c) Even though the users love the product, the fact that they would only use it couple of times a year means that you need to have lots of users, which circles back to the previous point<p>It sucks because the travel space really needs quality apps and I would like to believe that there is a way around all the issues for startups. But the fact remains that it is a bad idea for most people.

In the smartphone world you don&#x27;t need to remember to use the service. Service can use well targeted contextual notifications to remind you when it is relevant. Obscurity is much less of an issue for intelligent services (even if they are rarely used).<p>I believe that there is probably an opportunity to build these services that have never worked in the desktop world but can work in the mobile world.<p>Travel planning has other problems (e.g. all the money is in bookings and not itinerary creation). Hotel bookings are super profitable - and hence expedia can spend &gt; $1B per annum on adwords to re-acquire customers.

These are all real and serious challenges. LTV of an average user is a tricky one because it can involve 19 &quot;users&quot; worth $0 an 1 worth $500, but the price of an adwords click or whatnot will be set based on the $25 average value. But, you might have something for the other 19 &quot;users&quot; that doesn&#x27;t bring the average value up to that scale. It&#x27;s a legitimate difficulty.<p>The acquisition&#x2F;reacquisition and learning to use some specific software paradigm is a legit difficulty. Something that works for a hotel concierge using it daily may not work for an occasional traveler.<p>Real problems.<p>OTOH, I think that ultimately &quot;travel planning&quot; or something to that effect is not impossible, just difficult. Review sites like Yelp are great for finding something that is popular but not terrible on average, but I have gotten far more mileage out of guide books where the author seemed to have tastes that I enjoyed. Usually I don&#x27;t have one, but.. There is still a ways to go.<p>It would be facetious to seriously suggest some solution because obviously these things need to be banged out in the real world, but I can imagine all sorts of things that <i>might work</i>. How about you enter the location of your accommodation, tick a few boxes for your budget and travel modes (walking, taxis) and it spits out a decent guidebook chapter. Local walking maps, restaurants, bars, local gigs for this evening. Some explanations about local tipping norms, buying train tickets and maybe a one page phrasebook. Give me an app where I can push a button to do this from a Cafe&#x27;s wifi and I&#x27;ll at least give it a try. If I can print it out, I might.<p>Maybe a person could be in charge of a city or part of one. Maybe not. I dunno. The idea that good ideas and execution can&#x27;t penetrate this industry doesn&#x27;t sound convincing to me. I have no doubt that its hard but I also wouldn&#x27;t be surprised to see startups take off that really nail informational based stuff for travelers.<p>One upside that the commercial realities of this industry can offers is a multitude of opportunities to make money from having a userbase . IE, if you have 1,000 active users in a city on any given day, that&#x27;s enough to make something.<p>In fact, I think it&#x27;s something that&#x27;s accessible for people to have a go at. Even authoring a local guidebook for your city (provided it is not New York or somesuch, in this case, pick an area). Keep sections up to date with weekly info and release it as an evoke, app or whatever.<p>Information is still what the traveller needs, IMO.

I had to laugh when I saw this headline.<p>I&#x27;m planning a road trip. And I have been actively searching for a &quot;road trip planner&quot; site.<p>Whatever Yahoo had at the link he mentioned apparently is gone; it just goes to the Yahoo Travel page.<p>And everything else I found was complete garbage. &quot;Wrap a Google Maps Directions page with something to put pins in the map near the route for certain categories of attractions&quot; is as far as any of them went.<p>I don&#x27;t know what Yahoo&#x27;s &quot;Trip Planner&quot; was about, but given the overall lack of ANYTHING like a decent road trip planner available, I&#x27;d have to guess that it also sucked. Otherwise some of the competing sites would have stolen at least SOME of the obvious features.<p>What was missing, you ask?<p>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.<p>2. A way to print out area maps and contact details for each of the interesting sites.<p>3. A way to sort the sites and travel details by day (I&#x27;m planning a multi-day road trip).<p>This is for the <i>MVP</i>, and shouldn&#x27;t take a competent developer more than a week working with Google APIs or equivalent. A <i>good</i> developer should be able to crank this out in a day or two. I&#x27;m tempted just so I can use the functionality to plan my trip!<p>I have to assume that the dozen or more sites that I looked at were made by people thinking &quot;I&#x27;ll make a road trip planner!&quot;, 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.<p>Bonus features (post MVP):<p>* 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.<p>* 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. &quot;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...&quot;<p>* Include AirBNB locations on the map in addition to hotels, but ONLY show both near the end of a day&#x27;s drive (corollary: give it a range of how many hours you want to be driving per day).<p>* Let me put in preference categories of food, and after planning a route, look for restaurants near where we&#x27;ll be at breakfast, lunch, and dinner. Double-plus bonus: Only recommend restaurants that are <i>open</i> at the time I&#x27;ll be there. (Yes, Google does have a first approximation of this information, though it&#x27;s often spotty.)<p>* 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!<p>* Let me filter attractions that get terrible reviews, so they don&#x27;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&#x27;t matter, but if there are only a few, even one more can be relevant.<p>Is this a good business plan? Heck if I know. I only know that I <i>really</i> want a site that does all of this right now (or at least points 1-3). And I sure-as-heck <i>would</i> 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 places can be found in the middle of nowhere, then it would be more popular?

Tripit looks to have had a reasonable exit before this article was written:<p><a href="http://www.crunchbase.com/organization/tripit" rel="nofollow">http:&#x2F;&#x2F;www.crunchbase.com&#x2F;organization&#x2F;tripit</a><p><a href="http://www.crunchbase.com/acquisition/0551c63d066e0afe86046a40878ebbeb" rel="nofollow">http:&#x2F;&#x2F;www.crunchbase.com&#x2F;acquisition&#x2F;0551c63d066e0afe86046a...</a>

Something clicked in me when I read the title &amp; article: this is all true. I made one travel planner few years ago and decided to open source it some time later, when it become apparent that it&#x27;s really hard to get decent traction with it: <a href="https://github.com/cwiz/GoFree" rel="nofollow">https:&#x2F;&#x2F;github.com&#x2F;cwiz&#x2F;GoFree</a>

I&#x27;m not sure it&#x27;s a matter of frequency, but rather a matter of value that the service ultimately provides.<p>Biggest concern with Google&#x27;s business model initially was that they are &quot;just a search engine&quot; meaning they don&#x27;t get as many page-views as portals. However Google managed to make more money than portals because ultimately they provided more value to the adviser (less impressions, but more targeted). At the end of the day, Google&#x27;s service was intrinsically valuable - if they charged an annual fee to access the search engine, lots of people would pay up. The business model extracted that value, albeit in a different fashion.<p>You can&#x27;t monetise trip planning with advertising indeed because there aren&#x27;t enough users to make that model work. But if it&#x27;s a valuable service - you should be able to charge a small fee for it. &quot;We&#x27;ll help you plan your trip for $10. Or $20 if you want us to put in some human effort&quot;. Given that it takes X hours to plan a trip, and a user&#x27;s average wage is $Y per hour, some number should make sense. And of course the service would generate leads and other commissions.<p>Would anyone pay $10 for a service that planned a trip for them? I&#x27;m afraid not many people would, which means it&#x27;s just not as valuable as people believe it is.<p>Up-market travel agencies plan trips for wealthy clients for free - there&#x27;s plenty of commissions to go around - so that model works. Trip planning &quot;software&quot; however doesn&#x27;t seem to provide enough value in its current form, but that doesn&#x27;t mean it isn&#x27;t feasible. If someone booked my flights, hotels, restaurants, tours, sight-seeing, theatres etc for a 2-week journey for me, they&#x27;d probably have a decent revenue stream from commissions alone (hotels pay 15%). Hell, I know a guy that plans trips for high-net-worth individuals and takes 10% of everything they spend.<p>I think the problem is that too many startups are afraid of the human element involved - having people make recommendations doesn&#x27;t scale - they say. However a semi-automated approach, that gave you a real PA &#x2F; concierge service throughout your trip would actually provide sufficient value imo. I know many wealthy people that would pay significant sums to have the whole thing planned (and booked!) for them in advance. Monopolise the up-market niche of VIP travel planning, before going mass market and you have a shot at a profitable business.

Well, I actually worked on Yahoo! Trip Planner (making it internationalised). There was zero engagement indeed, but everyone knew it was a crap idea then, at least in Europe. No idea how trip planner recruited ANYONE!<p>Yahoo is good at one thing slapping ads on content and making loads of money from it. Everything else they need to stop doing.

&quot;In fact, Americans are notorious for shirking vacation, clocking the lowest rates of vacation on the plane&quot;<p>That&#x27;s because America is one of the very few 1st world countries without mandatory holiday time. 25 days of paid holidays + unlimited sick leave here in the EU are the required minimum by law.

The other bad idea, local travel experiences, there were hundreds of them, but it&#x27;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.

Yet the travel startups keep coming. Case in point: Travel blog Skift.<p>However, one trend I&#x27;ve noticed with travel review site TripAdvisor (which has been around for 15 years) is it&#x27;s becoming a Yelp alternative. In that sense, it gets more of the regular activity that the OP referenced.

This fits perfectly with my startup food-chain theory.<p>In the internet startup world, there is an invisible food chain, whatever &quot;higher&quot; models will eventually &quot;eat&quot; &quot;lower&quot; models.<p>A travel planner, with low frequency, no real pain, doesn&#x27;t stand very high on the food chain.

I don&#x27;t travel a ridiculous amount, but TripIt is great and very sticky. Easing the pain of travel makes it worth your while. And knowing when I happen to be in the same city as a traveling friend is invaluable.

I have just used Owegoo.com for hotel and flights. Creative filters, not only A to B. Swedish startup, not perfect but a very interesting start. On www.owegoo.com they also have a lot of city guides.

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.

It feels like the author likes to see his family suffer and fundamentally misunderstands reality:<p>&gt; 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.<p>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.<p>And this is probably why nobody really gives a damn to use such things.

I remember the sites to search for airplane tickets like Hipmunk, Kayak or Expedia, they have the recognition so perhaps they can add travel planning.

Cost to find and learn learn new travel planning software &gt; cost to plan trip yourself with the internet

After wedding planning software...

How is the problem &quot;If I don&#x27;t remember it, I won&#x27;t use it.&quot; solved?

Based on the comments to the article, this is a year old (still valid, just a bit old)

I failed a travel planning start-up in 2007. Way before our time, I guess.

&gt; Americans are notorious for shirking vacation, clocking the lowest rates of vacation on the planet<p>As if they really have a choice in the matter.