Interested in Making Travel Easier? You can help!

I would love YOUR help.  Anything you can contribute in the way of comments to this blog will not only be helpful to me and my partners, but it could be to you – for your own needs in the near future.

Here is a startup idea … a travel site that builds travel plans for YOU – as an individual – based on YOUR preferences that the site learns over time.

Take me.  I love to travel.  I love to add it to business trips.  I love to do it last minute.  But I have – like each of you have – a bunch of things that are relatively unique to me.  I want to see as many things as possible.  I don’t like cars and taxis in cities with a lot of traffic.  I love trains and subways.  I would rather stick needles in my eyes than lie on a beach and soak up the sun.  The more adrenaline generated by an activity, the better.  Basically, I want to “experience” as much high energy activities as a possibly can in as short a time as possible.  Yes, I am off the extrovert scale.  But … I also have some idiosyncrasies to this profile – I love cathedrals and other great architectural buildings and I actually don’t mind shopping (I am so laying myself bare in this blog!).  

Sure, I know there are hundreds of travel sites and services, but this only makes the need stronger.  Most of these sites are either way too narrow in the problem they service or they … well, they suck.

For me, the closest travel book/app combination are the “Top 10” travel series.  I love the idea of lists of things to “hit.”  The challenge, of course, is that the list is not MY Top 10.  If I find 4 or 5 interesting, it is a massive win.  Imagine if I could get MY Top 10 – created dynamically for me.

Anyway, almost enough about me.   I see the site being something I go to on my PC (who am I kidding here, on my MacBook Air) to “configure” my travel and then have it all pushed to my smartphone for the travel … including a customized map, integration with my calendar, any electronic tickets embedded and so forth.

With that high-level background, here are the high-level use cases to drive the travel experience:

(1) It is February in Ottawa (i.e. approaching absolute zero) … I have a week open in two weeks’ time.  Please suggest a vacation.

(2) I know I want to go to Spain for 10 days next month.  Suggest a travel itinerary for me.

(3) I will be in London for business.  My calendar is up-to-date.  Fill in the remainder with things I would like to do based on where I am already staying, the weather forecast and so forth.

OK, this has been a lot of rambling on my part.  If you have made it this far, thanks for hanging in.  Now, your mission, should you choose to accept it … please add comments on what you like about current travel sites, what drives you crazy about travel sites and – most importantly – what do you wish travel sites would do and just flat out don’t help you with at all.  Or … just anything that relates to better travel even if it has nothing to do with software or technology.

Thank you in advance.  It is my sincere hope that you experience better travel – customized for you – soon.

7 thoughts on “Interested in Making Travel Easier? You can help!

  1. For pleasure trip (or business trip), I would want it linked to so that it would tell me ‘hey, you’re in Clevland on September 17? great. Blue Oyster Cult is there on September 18th”.

    Or, linked to and/or to inform me “you’re in Boston on Aug 12? great. Red sox are at home on the 13th (afternoon game).”

  2. closest i have seen is as they have very simple filters on preferences so one can find a ‘theme’ and a bunch of choices that are say accessible by direct flights from Toronto with less than 6 hours flight time.

    for us the challenge is often being able to find the right local resources. while google helps it throws up too much noise. for example we love to walk and pedal (as opposed to more challenging cycling!) and have done so in the uk, france and italy. its a real challenge finding good resources … very hit and miss.

  3. 1 Question – “How do you currently solve this problem for yourself” ?

    Start there, and find others like you. Simplify that process and you have a potential business 🙂

  4. I love your challenge being a travel planner junkie! I totally agree with you in that planning is a fine art and I use many web sites to come up with a great plan (when the trip doesn’t lend itself to spontaneous travel).

    I see the planning as happening in several stages of which I have done a quick summary below:

    1. Determine the destination. This might be per-determined as in your use cases 2 &3, or not as in 1. If not, then I think that the destination planning is fairly complex out of an airline dead-zone like Ottawa but I use a combination of nearby airport web sites to see what airlines and direct destinations they have so that I don’t get all excited about a spot that is 4 hops away.
    Once I have a reasonable destination, then I use Kayak or similar sites to find the best flight.

    2. If choosing between a few destinations of which I know very little, I use sites like or to see what some of the highlights in a country or area are. Travel blogs can also be helpful but it is a lot more work to wade through all of the text. It is cheating but gives a very good high level look, and is great if you like active stuff (like you and I both do).

    3. Of course factoring into the destination planning is the time of travel and knowing when stuff will be accessible or not based on that, so that is another angle to look from. For example, picking the perfect island for diving and then going there during the months of no visibility.

    4. Once the destination is selected then I use a combination of Lonely Planet and Frommers to plan travels points and activities. Tripadviser is also getting better over time.

    5. For accommodations, I either use airbnb or vrbo or hostelworld or cheap hotel sites depending on when and where I am going.

    6. Then there are all of the other sites like local transportation, entertainment tickets (Goldstar is awesome for the US) if required, etc.

    7. Lastly, it is helpful to have something like tripit if you have lots of details to keep track of.

    Okay – probably way more than you wanted to hear but I got carried away. 🙂

    Good luck!

  5. I also like Kayak for getting there – I especially like that their interface is easy to use and uncluttered and yet finds me the same results as a way more busy (and seemingly feature-rich) site like expedia (for example). And yes I’m that person who checks both (really multiple) sites to see if they give me the same results. 🙂

    For “what do I want to do while I’m there” I like to look at the boards on Trip Advisor for a specific city, once I know where I’m going, and read up on what the Top 10 attractions are, restaurant reviews, and lots and lots of reviews of accommodations etc on Trip Advisor, as well as other review sites. I also often read wikipedia or wikitravel entries on a destination.

    If I’m really really organized and going somewhere like Europe I will even go to the library or bookstore and leaf through some actual physical travel books like Rick Steves’ guides. Although admittedly I haven’t done this in a few years, so not sure if real hard copy books would still make the cut.

    One thing I do find frustrating is that there is so much info out there, but so much of it is noise, and I have to manually sort through it all to find the nuggets. If there was something like Kayak that was really simple but that *really* was able to actually show me what I want, and that didn’t take me hours and hours of reading online to find it – that would be awesome.

    We seem to hit use case #1 every February, and I always end up doing the same thing: I manually comb through pages and pages of last-minute deal sites, spend hours and hours reading reviews of resorts, agonizing over flights, and then picking what looks like the least bad compromise. There’s got to be a better way!

    • Hi Mindy.
      We don’t know each other but I wanted to comment on your posting because it got me thinking.
      We have the use case #1 every Christmas – sifting through tons of ideas trying to figure out where we can go from Ottawa for a week or two that is interesting and fun and doesn’t require 24 hours on a plane. I am tired of resorts so we always end up in Central America.
      That made me think that it would be interesting to find an effective way to share knowledge from one person to another. For example, I spent weeks this year planning what will hopefully be an amazing two weeks in Panama. It would be awesome if there was an effective way to share some of that info so that it could be re-used if someone was looking for something similar and just wanted to take my template and adjust to their own preferences and parameters…

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