Captainwise. A new way to fly.


Have you seen the movie ‘Up in the Air’ with George Clooney? If you have, then you likely remember the final scene, where the protagonist walks into an airport and stares at the flight board, deciding where to travel to next from an endless list of cities.

In a nutshell, that’s what Captainwise is. A refreshingly simple travel page which will arrange your vacation for you, provided you can list a point of departure, a total budget, and the days you plan to travel. Once you’ve submitted the necessary information, the system will automatically compile a list of cities to which you can travel for roughly the price you provided, pre-selecting available round trip airfare, along with accommodation.

The site compiles information from more prominent travel sites such as Skyscanner, and, but offers a few distinct advantages which set it apart:

1. It’s almost too easy to use. You can’t complain about a program which allows you to plan an entire vacation in literally a few clicks of a button. The interface is centered towards providing a pleasant user experience, and it certainly manages to do so.

2. Choice! Nobody likes being told what to do, but they don’t like having to do it themselves either. Captainwise seems to have banked on this, and realized one of my childhood dreams in the process. Providing an accurate list of potential domestic, and international destinations, with ready flights, and hotels allows you to select from a diverse set of options and hand pick the details to your own vacation.

3. A feel good story? Ok, call me sentimental but I do identify more with brands that have an interesting background. This could be regarding the company itself, or its executives. It’s the reason I prefer Virgin Airlines to British Airlines, Ford to Chevrolet, and Costco to Wal-Mart. Captainwise is the latter of the two possibilities. It, like so many startups is the creation of five guys under 25 (link in Greek) who decided to revolutionize how people traveled, and in doing might have revolutionized an entire industry.

In essence, that’s what makes this idea great. It’s not just another addition to an already condensed industry. It’s something that in the coming years can change the way we approach travel altogether. It responds to people’s demands to be more independent in how they go about arranging their free time. No more awkward meetings with the travel agent, no more having to deal with frustrating booking sites, and no more asking where to go.

The page allows you to enter minimum information for maximum choice. A hard combination to beat.

I’m looking forward to see how the site develops in the near future, and whether it can continue to pick up steam. They’ve recently performed a major overhaul of their user interface, improving the front-end, and diversifying the available starting points, which will hopefully give them a boost, especially outside of their base in Greece.

All in all, it’s certainly one to look out for in the future.


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1 comment

  1. Personally, I am a fan of Captainwise too. I am totally excited about the idea and also sympathise with the young Greek guys’s endeavour. Recently they received an $80k seed funding round. Hope they reach the stars.

    Regarding the site’s product itself, I think it would be very interesting if the budget you input in Captainwise also included the travel expenses during the trip e.g. food, coffee, transportation etc.

    Loved the article Panos, especially the upbeat tone and the eloquent writing. Looking forward to your next one!


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