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I've been working on a travel activities startup in stealth mode, but had to put it on hold because of other work.

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.

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't travel alot. My response was that while everyone doesn't travel often, there is always someone who is planning a trip. I don't think the frequency of travel is the issue--it's the logistics of it.

Enough of waxing nostalgic, I think I'll get my packages and libraries up-to-date and get back moving on my idea.



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I agree that travel planning is a common (and often bad) startup idea, but I disagree with the reasoning.

Part of the enjoyment of many trips, for me, is the planning. I get to learn about the city, see which places/activities I am most interested in, and gain some small level of insight into the location, the history, the culture, etc. I enjoy talking with friends about what we want to do while we're there, or asking what they liked last time they visited, so I don't feel a huge pain point here. There are certain aspects of travel I don't like planning, such as transportation, but that seems to be where travel startups have been most successful (booking flights, etc.)

Similarly, travel apps don't know what I like. A museum about a certain artist that I'm interested in? Great! A concert for a musical genre I don't have strong opinions on? Meh. And while the software could take my interests into consideration, inputting my preferences to useful levels of detail adds friction to the process.

Finally, I prefer my trips to be flexible. I rarely plan what restaurant I'm eating at; I'll walk around and see what looks good when I'm there. And if I see something near where I'm staying that seems interesting, I can do that instead of whatever I had planned for that afternoon. Travel planning generally strikes me as more limiting than freeing.

Perhaps there is something great that just hasn't been created yet, or maybe my travel needs are sufficiently unique that I'm just not the target market, but I'm not holding my breath.


Making the people building a travel app actually travel, what a concept.

My 2 cents:

It’s really hard to get consumers to switch behaviors for something they already can do through other means. Perhaps this is more efficient in some respect, but only if you ignore the inefficiency of changing your ways to learn a new tool, and further separate it from your existing communications medium (ie text messaging or whatever). I don’t feel like the value proposition is super high here.

In general people only tend to use 7 apps, and to create something for a rare activity will be very hard to keep in mind when you go to do it. So capturing the moment when people need to do it with when they find out about you is difficult to time… and that’s if you can convince them to try something new at all.

If you’re going consumer specifically for trip planning, I’d focus more on specific pain points versus “nice to haves”. It’s not clear from the website that pain points are considered. It also feels very structured, eg that you know how long you’d stop at a given place. In practice I don’t think many people operate that way, especially for a vacation unless they have reservations.

I’d suggest finding a niche with clear pain points that this solves, and then focus on that demographic. That may likely not include consumers.

Good luck, it’s really hard to make something new, put yourself out there, and know whether to stick with it or not. I’ve been down this road before. If you don’t try, it really won’t work!


Said more succinctly: It's hard to make a successful product that reduces the time people spend doing something they love to do.

Some ways I could imagine addressing this and the problem the article talks about:

* Aim to make travel planning not easier (i.e. less time-consuming) but more fun. Treat the app more like a game or media app where users spend more time planning their trip by using the app in enjoyable ways. Put a ton of discovery and browsing ideas for things to do in it. Pinterest for vacations and activities. Basically Instagram, but with a "book this" button next to that pretty sunset photo.

* Focus only on the parts of travel that aren't fun. Haggling over fares, logistics, reaching consensus with travel partners, etc.

* Support use cases beyond just travel planning. If it's also a commute planner, or "what do this weekend in town" planner, it may get used frequently enough to stay in a user's mind.


I think this is a good idea. Start small and measure responses from early adopters.

Make light use of software at first. Use existing tools to build a process before attempting to build an application.

Start with friends and family and their friends. Define the real problems that people have with current resources. What provides the most value to those who use your approach?

I have thought about this concept myself. There are usually very fun and interesting things to do and see in a travel destination that are not necessarily the primary, dry tourist attractions.

Travel memories are built around social engagements-talking, sharing, learning, experiencing. I think a solution that emphasizes these things would be beneficial and well received. But again, this will take some effort to sort out.

Good luck.


Amen. Definitely been sucked into and subsequently failed at Social Travel big time. I think that's a sexy one, there is an unsaid allure in it of being able to mix travel with running a startup. Such a crowded space, and most fail out the gate. Once you do the math you realize there is far more travel media out there than travelers, especially in a down economy.

Anyone who loves to travel and wants to get out more, but is stuck inside writing friggin code all day gets this idea at least once. "Wait! How would I combine writing code with travel? I know, I'll make my own travel recommendation site." The irony is in reality I traveled wayyy less as a result of committing to this idea. Bummer


Kudos to you for pursuing something that a lot of people are saying won't work. That takes some character! Especially in a difficult time for travel.

Your app looks great. As a full time traveler / nomad for 10 years, I don't have much of a need for itinerary planning apps on their own. But I would love to have social itineraries, where I can follow my friends' itineraries and share mine with them especially for serendipitously meeting up at random points around the world when our itineraries intersect. Yes, I've got an abnormally large number of globe trotting friends, but there are entire nomadic communities out there who are eager for this feature.

Are social features something you've considered developing further?


Hey man! This is what my startup is working on. Travel is a ridiculously cluttered industry, yet no one's managed to nail it. (I think because they're so focused on pure monetisation - skimming off bookings etc - they're less focused on the inspirational or emotional design side of things. We're pairing this with kick-*ss functionality). We're not launched yet, but I would love to get your feedback on our demo when it's finalized :)

I spent about 6 months building Itinee (https://itinee.com) which is a trip planning app focused on being budget conscious. I built it because my wife and I love to travel but my assortment of spreadsheets was a little intimidating to her. I wanted a platform that let us both participate in the planning process. Unfortunately, due to COVID, people aren't traveling so I haven't really put any money into marketing it or done any more development on it. I might revisit it once things get back to normal. I don't plan to do much more development until I get user feedback, though

A while back I was thinking about a trip planning product and my enthusiasm was deflated when I read Gary's post. I remember one of my main take-aways was that travel just isn't something people do very often. So even if they use and love your product, the chances of them remembering you the next time they need to plan a trip (a year later?) are slim. I ran into this same problem working on a product rental marketplace (bouncy castle rentals, wedding tents, etc) and it was definitely a struggle. We had to constantly acquire new users. That said, I wonder if there's something here if you focus on business travelers. (1) Some business people travel quite often and (2) Lots of people pay for travel agents or use internal resources to plan their trips.

Recently Paul English, the co-founder of Kayak, launched Lola. It's sort of like Magic or Operator but travel-specific. May be worth checking out: http://lola.co.

Another area I like about travel is safety. When you're traveling to a foreign place, it's easy to assume a given area is safe ("It's only 2 miles from the city center!"). I'd pay money to have access to a real local to warn me of areas to stay away from and let me know of things I shouldn't miss.


The "where do we want to go and when?" question isn't the hard part, though. It's finding venues and flights with the best group rates and windows. It's not so much the front-end logistics and discovery aspect that's challenging; it's the back-end logistics. Especially as the group increases in size.

I don't think any app is going to effectively take choice and discussion out of the equation. Attempting to do that, especially with a category like leisure travel, is asking people to let an algorithm plan their vacations. Most people won't go for that; they want a large degree of choice and consideration in the process. But the stuff nobody likes doing -- planning flights, searching for fares, booking rooms, etc. -- is where the pain points reside.


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.


This is great! I work as a dev on a related travel product (mentioned in a comment here actually) and our in-progress redesign has the things you mention as priorities (speed/clarity).

I'm going to go ahead and say travel apps in general suck, so I'm not surprised to hear your sentiment towards TripIt's iPhone app haha.

One thing that I appreciate is that you understand the difficulty in designing these kinds of apps. On the surface it's "oh. well it's really just a bunch of lists and buttons with labels and text", and I think that's the approach a LOT of travel companies take. They value the tech/info more than the way it's presented. Luckily there is a LOT of room for improvement in this industry, and with devs who care about experience and designers who understand tech we should be able to make a big dent. I honestly thought TripIt would be one of those companies though...


Fortunately for entrepreneurs, this idea seems to be catching on.

Unfortunately for consumers, it seems that the user experience is stuck in 2007. I still can't find a good app which allows me to plan a full trip at once, especially when I haven't entirely decided where I want to go yet. As someone who travels about once a month, I'd love to see something better than Kayak.


Thanks for the interesting example.

Couple of questions:

Not many people go on six week vacations, right? If you were planning a two week holiday, would you still be faced with so many decisions and complexity? If not, the market you represent would be limited to longer holidays, which may be a very small market.

Second, could an app provide you with a better service than your travel agent? i.e. is this a "problem", or is a "solved problem" because a satisfactory solution exists already?


Myself and 2 friends wanted to help people make smarter decisions on big purchases. This is our story of committing the cardinal sin of startups.. creating a consumer travel product.

The Product: https://www.getcluey.com/en/explorer/

Once described it as a load balancer for tourists.

It's still a work in progress, the data is not perfect, and it's more of a tool than a product at the moment. But we want to share the concept and trade ideas.

Similar tools have existed in the past but not to this level of detail. The ones we came across in our research were generally vague and seemed to always suggest the same places.

We're new to travel. It's going to be a battle, but we're passionate about the problem we are trying to solve. Travel can be indulgent, but there are a lot of important benefits too. Injecting money into small, local economies. Meeting new people, seeing new cultures - breaking out of the bubbles we can fall into day to day.

Cluey's goal is to allow people to quickly search and compare travel destinations. Looking for places for a balmy beach holiday in October within 7 hours flight of you? Hard but doable. Try to overlay that with popularity, cost, rainfall, safety, activities, language? Hope you have a degree in data science.

Some user feedback we've received: - I thought Armenia was dangerous and war torn, it's not? It looks beautiful. - I was going to fly to the Bahamas but its probably because it's so prominent on American media. I couldn't figure out where in the pacific it's warm without tropical drizzle. Actually there's heaps, a lot cheaper, and a shorter flight.

It's not really going to help you already know exactly where you want to go and do there. It's useful if you have limitations or specific needs. Eg a popular one seems to be young families who only want to fly X hours with their children and would like to see what the options are.


The author doesn't seem to go into why travel-planning software is not successful, except for that it isn't discoverable since people only use it once in a while. I think the same can be said for a lot of services, like handymen (Angie's List)

One other reason is I think that travel planning is hard. Getting multiple people to agree on a destination, hotel, fares etc is all hard work. So most people only plan things with people whom they're familiar with, like close friends and family. If there's already a communication channel open like texting or Whatsapp etc it makes no sense to introduce more friction by having travel discussion go through a different channel. I remember an app for couple communication, Between. It had a similar problem. Why add another communication channel?


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.

When I'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 & airfares.


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'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.

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:

- flight management - hotel booking management - local knowledge resources - tools for connecting with locals - language tools

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'm not sure but the tools on their own seem to do pretty well once you've put together your toolset.

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