Odyssail: Why is it so hard to book a sailing trip online?
Digital Next | Industry Savvy

Odyssail: Why is it so hard to book a sailing trip online?

on / by Loucas Papantoniou

Did you happen to hear the news last May of a Chinese labor camp forcing detainees to play World of Warcraft as part of a huge money-making scam? Well, I have another idea that might not generate any money to the guards, but will definitely cause pain with the detainees: try to book a sailing trip to Greece online! Seriously, my eyes were hurting, I got stressed, and had nightmares that I’ll spend all my summer in the rainy Netherlands.

My Odyssey and partying like it’s 1999

But let me start telling you about my personal Odyssey. It all started with lots of enthusiasm and cheers after finally convincing ten friends from the Netherlands to spend their holidays in Greece and go for sailing and island hopping (well, it was not that hard). After all, it was a safe way to enjoy the Greek summer, away from any riots and strikes. I assured my friends that I’d arrange everything and that in the end they’d only had to share the final bill with me.

So, with lots of enthusiasm I typed in Google ‘sailing in Greece’ and started clicking on the top ranked results. If only I knew that by typing these three words I had opened a time gate that allowed me to travel back in 1999. Not Prince’s 1999, when it’s judgment day, the sky is purple, people are running everywhere and Prince is singing that he’ll party like it’s 1999. No, I mean the ‘www’ 1999, remember? The one with elaborate pages and more content that James Joyce’s Ulysses, crappy ‘150x90px’ pictures, tables longer than the Greek tax administration’s spreadsheets and more links and call to actions than hairs in my beard.  If you can’t remember how did 1999 look like, let me refresh your memory with these lovely sailing websites that ranked the highest in my Google search: odysseysailing, greecetravel, sailgreece, sailingissues, sailionian.

Snapshot of a typical sailing website
Snapshot of a typical sailing website

Like I care…

Anyhow, I started browsing them and as you can imagine I got completely overwhelmed by the information. Tens of different boats to pick from. Do I want a Bavaria 51 (that is in feet, apparently) or an Ocean Star 51,2? I clicked, and then I got to the tech info accompanied by the technical sketches and images the manufacturer provides. Mmm, do I care that my water tank is 940lt and my diesel tank is 430lt? Honestly, no! And if I did, I would google it. It’s like booking a plane ticket, and you get told what the capacity of the gasoline tanks of the Boeing 787 you’re flying with is. Do you care?

Do I really need all these specs? Try to spot the call to action

Anyway, after spending a couple of hours totally baffled by the info, I decided to try 48options. What 48 options essentially does, is that forwards your yacht charter request to all the sites affiliated with the site. After all I’d at least bypass all these terrible websites. What I got as a result is a full inbox with overpriced offers, and prices that skim as the summer passes by. I still receive offers although the requested date has passed. Of course, I want to unsubscribe from this service. But guess what? No unsubscribe link or option.

All I want

Time to make the long short, stop grousing, and get to the point. What I want from a yacht charting website is a booking form with all the relevant information:

  • A calendar: to provide the date I’m planning to plunder the islands with my rented pirate galley.
  • Destination menu: a  drop down menu with the available places to loot, heh sail I mean.
  • Passengers: the number of compadres in this journey.
  • Option for a skipper: the option to have a captain that will AARRR and sail you to the best beaches.

and what I want to get is:

  • an all inclusive price.
  • and a bank account to transfer the money.

Is it too much that I’m asking for?

Why should renting a boat be more complex than renting a car or booking a flight ticket? At the end of the day, chartering a yacht is a quite lucrative business targeting mostly well off customers.  From discussions I had with our skipper, the business is still growing despite the harsh competition and the crisis. The margins might be lower than before, but still it’s a business with room for growth. Nevertheless, the same people that browse a polished page of Hilton or Hayatt,  have to go through a user experience that is buzzillion years behind when booking a yacht.

Why is that?  If you ask me, I think the sector is full of skippers that became entrepreneurs by accident (or luck). People that love to feel the caress of the wind on their forehead, smell the iodine of the sea, and get a nice sun-tan but still don’t have a clue about online marketing and business. Then you’ll ask me  what about web-design agencies; they are the ones designing the page, right? In this case, I could blame the idiosyncrasy of skippers-owners. They are men that are used to manage and control everything on board. They might have a distorted view of what a good webpage really is, but they still want the webdesign agency to follow their wishes and vision. Another speculation I can think of, is that it’s pure skimpiness by skippers-owners’ side. A sailing website has to be redesigned during the off-season, when there are hardly any bookings hence guaranteed income. It could also be that island hoping in Greece, on board, definitely pays-off no matter the hassle and lousy experience before sailing.

What do you think? Do you have any personal experience that you’d like to share with us?

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Article by

Loucas Papantoniou

Usability Analyst @ Usabilla Jack of all trades, immersing passionately and sometimes obsessively in my interests. Greek living in A'dam, missing the sun.

Share your thoughts

  • Nathanael Dimitris


    I would agree with all you mention above, especially with the calendar and proposed Destination menu but I have one objection –> the water capacity of the yacht. This is of the outmost importance for the comfort and freedom to sail. When you have women onboard you find yourself with an empty water tank every 6 hours. So what happens is that you need to call on ports that can provide you with water every day… compromising your freedom of decision where to sail. And as you know well one may prefer to spend his day at anchor in Keros or Levitha or even at the dock in Heraclia than in Naxos marina. This comment comes from somebody who sails for a month with a total water consumption of ~ 100 litres :-)



  • I truly understand you Loucas as I have encountered similar situations. In my daily job I have ended up developing “e-shops” which do not display prices because of the my clients’ fears that competitors would know how much their items cost!! So you get a site where the client would add to cart and go through a tedious e-shop process and then at the end he/she would be greeted with a form instead of a payment facility! And speaking of “e-shops”, I have a client who wants to show items that he does not have in stock (and which he does not intend to get), so that his e-shop looks like it has a lot of items … and the stories go on and on and on … :(

  • Oh dear, how embarrassing!

    Came across this post somewhat accidently, and it turns out our site is one of those mentioned as a 1990’s style disaster.

    Loucas, the only thing I can say in defense is that we actually have a new site, http://www.sailgreeceyachts.com that has I hope a slightly better visual look and a clearer indication of how to get the information you want. I think we had better look at fixing up the old one. It isn’t from 1999, but you are not far off ;P

    Hope you had a great time sailing!

  • Hi Giannis,
    I don’t have a clue what your old site looked like, but the new one must be a big improvement. Looks professional and I can easily find my way. If you’d like to get some feedback you could set a simple (free) Usabilla test in a few minutes and invite for example your Facebook fans to give feedback. Try it out: http://usabilla.com.

  • Hi Paul,

    Thanks for the kind words! I am trying out the usabilla test(s) right now, it looks like a great tool!

  • Hello to every one, the contents present at this web page are really amazing for people knowledge, well, keep up the nice work fellows.

  • Hi Loukas,

    I totally agree with alot of what you’ve said here especially about skippers becoming entrepreneurs although I think in this context I’d rather have a skipper who became and entrepreneurs rather than the other way round!

    Some info should be shared but you’re right it should far simpler than it is at the moment. These guys have got it right http://www.atlassailing.co.uk

    Great Post.

  • I am a sailing captain on my own 20mt Kanter Ketch. I agree in how frustrating can be to find the right sailboat.. if you look to hire just your cabin on a yacht the problem is similar. Now since your post some companies are making this searches easier. I did the same creating my own platform to search and compare different charter companies proposals both for entire boat charter and for cabin charter. We are working on increasing the suppliers and improving the usability.. giving the right information the a traveler may need and not just all the technical details of the boats! :) Check it out here https://intersailclub.com/
    Enjoy sailing!

  • christospapadimitriou


    Check this one…

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