Slightly intelligent travel booking sites?


Staring out at the dirty slush piles in Cambridge I am thinking it would be nice to go to the beach. Twenty years ago when people asked what good Internet commerce would be I gave them the example of a Web-based travel booking site. Here’s how I said that it would work….


  • where you live
  • when you want to go
  • what kind of vacation you want to take (beach, learning, hiking, skiing, whatever)
  • rough price range

The system would then scan the airline and hotel databases (which existed back then though they weren’t Web-accessible in the first years of the Web) and find a place that

  • you could get to on a non-stop flight for a reasonable cost
  • where hotels were available at a reasonable cost on those dates

I touted the advantages of my system: “Instead of you just picking a handful of places that you can think of, possibly overlooking some where hotels and flights are practically empty, the system will search all of the possibilities.”

Did anyone ever build my fantasy travel booking/searching site? If not, why not?


  1. Kyle Marek-Spartz

    February 22, 2014 @ 6:57 pm

    1 gets you some of the way there.

  2. Murali

    February 22, 2014 @ 7:05 pm


    I don’t know if this site meets your requirements, but the original goal was to make travel “not suck” — as in, instead of just going for the cheapest available, it also takes into account the comfort of the trip.

    I never used it to book travel myself but I do know the founder/CEO.

  3. philg

    February 22, 2014 @ 8:13 pm


    Murali: Hipmunk covers about 1 percent of the distance between Orbitz and the kind of site that I am talking about. Notably Hipmunk requires that you already know the destination, i.e., that you already know the answer to the question you were hoping to get a computer-generated answer to.

  4. Jani

    February 22, 2014 @ 8:15 pm



  5. J. Peterson

    February 23, 2014 @ 3:23 am


    I’ve come to regard the chore of plowing through Kayak/Hipmunk/TripAdvisor/VRBO/etc to plan a trip as only slightly less odious than the line at TSA. At least in the days of travel agents you could simply blame somebody else when things went wrong.

  6. Tom

    February 23, 2014 @ 4:12 am


    Amadeus provides exactly this type of product to airlines and travel agencies. Look for Extreme Search or Affinity Shopper. Some airlines and Online Travel Agencies are integrating it in their web site.

  7. Arbitrage

    February 23, 2014 @ 7:49 pm



    My fantasy travel site is better than yours. You pop in the dollar budget and temperature/inches of snow/water-p and it does the rest for you. After all if La Paz is cheaper than Costa Rica why not?

    The tedium (and dimensionality) of booking flights, car rental and hotel and doing the arithmetic and logistics across all combinations is almost as much work as going on vacation.

    Something good for a bored hacker to take up?

  8. John Rothlisberger

    February 24, 2014 @ 3:09 pm


    Check out Google Flights:

    Put in the starting point (e.g. BOS Boston), and from the “Stops” drop-down select “Non-stop”. This will show you prices for local (within your region) destinations that are direct flights. If in the destination field you then enter a region name (e.g. South America), the map will re-focus on this region. You can zoom in and out at your heart’s content. If non-stop flights are too restrictive, change it to “up to 1 stop”.

    I suspect general purpose tools fail because there are far too many variables at play:

    – How do you reliably pick a hotel? Have you never spent hours reading hotel reviews? I have.
    – Infrastructure at the destination. Some people like comfort, others prefer rough. How do you quantify and categorise that in a way that satisfies everybody?
    – How do you rate a beach? A city? A country? How do you algorithmically make something preferable over something else, based on a few hundred dollars difference on a potentially multi-thousand dollar trip? And if the difference between La Paz (freezing cold) and San Jose (warmer, closer to the US) is only a small percentage in price, then why not just always send people to the safe bet, which is basically what happens now?

    I travel at least once a year, and every single time I thoroughly research it. And I have yet to find any tool or website that comes remotely close to being able to tell me what I want.

    My most recent example: I wanted somewhere warm in November/December, a not-too-long direct flight from London, which was child friendly. This criteria immediately ruled out e.g. Mexico and Florida (10 hour flight), Egypt has a lot social unrest (this wasn’t explicitly in my criteria, but immediately ruled out), and I was basically left with the Canary islands. Now there are several islands, and each has a different climate and vibe. So now I’m trying to decide which of the islands would suit my 3 and 1 yr-old daughters. OK, so now I’ve picked the island, now which hotel based on price, features (some of which I didn’t even know I wanted until I started researching), location, and price? Do I want a hotel, or a villa? OK, now I think I’ve got a hotel, how am I going to get there from the airport (transfer, taxi, or rental car)? What activities do I want to be able to do when I’m there? And so on…

    A lot of these things just require quality data that will just never be there, or that’s impossible because it is subjective in the first place.

    The UK is very big on package holidays (not sure about the US), I assume because there is so much choice, and it just takes the guesswork out of a holiday. You are trusting the package maker’s discretion about the combination of features, and you pay a single fee, and everything is included. Sort of like a cruise, but on land.

  9. Tom Howard

    February 25, 2014 @ 8:15 am


    Hey there,

    I’m one of the founders of Adioso; we got a noticeable amount of traffic from this post, so thanks to Jani for mentioning us.

    The type of app you’re describing is very much what we’re building.

    We already support searches like these…

    The other features you describe are very much in our plans.

    The reasons this hasn’t done before are…

    1) It’s totally at odds with the way the decades-old travel industry infrastructure works

    The reason every flight search interface conforms to the same Origin/Dest/Depart date/Return date format is that that’s the way Sabre (built in the 60s) works, and every system built since (Amadeus, Galileo, ITA Software) has been built to be compatible with that.

    Aside from lack of will/incentive to innovate, the reason more powerful search infrastructure has never been built is that it’s just really really hard. The global flight inventory (including schedules, fares, availability) is incredibly vast, is incredibly rapidly-changing, and is somewhat fragmented (increasingly so as airlines and distributors wage war against each other), so assembling a comprehensive cache of airfares with adequate accuracy is near impossible.

    As another Tom mentioned, Amadeus now offers the ExtremeSearch product, which Adioso uses in addition to our own proprietary search engine. ExtremeSearch is an excellent product, but it still only has inventory that Amadeus distributes, and is missing many of the low-cost airlines that cover many of the best vacation destinations (which is why we complement it with our own search engine to provide LCC results).

    2) Cost & barriers to entry

    Most radical tech innovation happens in small startups. Exactly why this is this case has been examined extensively elsewhere, but for the sake of this discussion, let’s accept that as fact.

    Most startup innovation these days starts with a couple of hackers spending a few weeks/months knocking together a prototype in Ruby/Python/PHP, releasing it, getting some early-adopter traction, then if it’s going well, getting some seed funding to grow it.

    With travel, however, it’s just not possible for a couple of outsiders to get access to travel data platforms to hack prototypes against. To get access to any product from Sabre, Amadeus or ITA Software, you’re looking at a commitment of hundreds of thousands of dollars per year before you can start building anything, and it involves contracts that take months to negotiate, then more months of implementation.

    And that’s before you consider the challenge of growing a big audience in a market that’s dominated by huge players with deep pockets, and when your product has no inherent network effects. And it’s also before you consider how slim are the commissions on airfares and (to a lesser extent) hotel bookings.

    Exactly how Adioso has managed to make it this far is a story that will be told in full some day, but be assured it’s been damn hard. And it’s taken 5 years so far, and we still have a lot of ground to cover.

    With all that said, we’re now closer than any other company in the world to delivering the product you describe, and our momentum is only growing.

    I’d be happy to hear any thoughts you (or anyone else) has –

    Adioso Co-founder

  10. David

    February 25, 2014 @ 12:33 pm


    I thought Hopper took an interesting crack at this problem.

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