Home » Travel Roulette. A new spin on taking a vacation and making it exciting

Travel roulette is a new spin on taking a vacation

Taking a vacation anyplace takes planning and thought. At least, that is how it should be. Back in the day when I was working on ocean cruise ships, I would get vacation time and not have a clue about where I wanted to go or what I would like to do. The solution was, what I call,  travel roulette. It’s a complete crazy and exciting experience!

making a good decisionWith just a couple of weeks break on my hands, schlepping back to South Africa was a mission and a loss of time. So, I figured I would vacation from the general area I disembarked. If in the States, disembarking from Miami or Ft Lauderdale, I would try and think of a place to go relatively close by, avoiding high costs as best I could. The same applied if I disembarked in Europe. But, the issue for me was that I wasn’t sure where to go.

I had a bucket list – places I wanted to visit but these were aimed at longer periods of stay – places like Japan, Cambodia, etc. They did not fit into a 10-day vacation plan for me.

Finding a place to go

I needed a place to just take my time, not travel too far and a location that would allow me to chillax and recover from the work I was vacationing from. But where?

Where to go?

Decision madeThe idea of a vacation would be somewhat stressful. As my girlfriend, at the time, would probably be working onboard, she would not be available to travel with me.

This meant I would be solo.This was another reason not to go for my bucket list destinations as these would be places that I would like to share in the experience.

So, it became stressful and not enjoyable trying to define a location. It happened one day that I could not decide on anything.

I procrastinated and e­­nded up getting off the ship and going to the airport in the hope that I would have some epiphany on the way. Naturally, I did not. I arrived at the airport totally clueless.

An idea of travel roulette came to me from the deep recesses of my arguably unhinged mind

I remember it well. I was feeling a bit depressed. I had to say goodbye to my girlfriend, a dancer on the ship, and suffer that separation anxiety along with not knowing where the heck I was going. I ordered a coffee and sat for a good hour just feeling stupid and sad.

3 espressos and one latte later, I dejectedly left the coffee place and walked aimlessly out into the departure hall, thinking I should grab a cab and go to a hotel and try and get some plan going.

I looked up at the departure boards and the thought came to me. What if I just tried to get a flight to someplace that grabbed my attention on the board.

Something that may resonate and fuel me with some enthusiasm? I scanned the departure boards, dismissing the flights that were leaving within the next few hours. I focused on the afternoon and evening departures.

Plenty of flights going to major US cities. Most I had been to or had no real desire to visit this time around. As the times proceeded later in the day, the flights got more interesting.

Taking a blind leap of faith

 I eventually settled on an evening flight. Argentina! Buenos Aires. I had never thought of going there…at least not with any serious consideration. Why not? I got excited. So, I headed off to the American Airlines desk to see if I could book this.

The woman behind the desk eyed me with some suspicion. I am not sure why. Maybe too much coffee and my sudden excitement had dilated my pupils or maybe I seemed a little crazed with the caffeine.

“You want to book a one way?”

“No,” I replied with what I thought might be a calming smile. Probably not. “Return”. I gave her the date. Traveling on a British passport meant I did not need any kind of Visa (at the time), and so I handed across my card and confirmed the return flight. The flight was at 11 pm. I was going to Argentina! Awesome. 40 mins before I had had no idea where I was going.

This was a mind-blowing experience. It was kind of like winning a prize. Hard to explain. But I thought it was cool. Then I realized, as I dragged my luggage behind me, I was 12 hours too early.

It was 11 am. The thought of having to hang out in the terminal for 12 hours was not appealing. Screw it, I thought. I will get a day room and that way I could freshen up and sort myself out. I would text the lady and let her know where I was going and I would try and find accommodation in Buenos Aires.

My travel roulette days were born

 I got a room at the nearby Days Inn and relaxed onto the bed while I spent an hour looking for someplace to stay in Buenos Aires. I found it. I booked it. I was sorted!
Texted my girlfriend and received the response “You are insane!” I chuckled like a naughty schoolboy and spent the afternoon and early evening with a nap, a shower, a room service lunch with a cold beer and read up on travel tips for Argentina. This was the beginning of my new pursuit of travel.

travel roulette gameFrom this moment on, I decided to take my short breaks playing Travel roulette. I have been to so many places that I never thought about going to and most times been happily rewarded for my gamble. Only twice did I make a couple of bad choices.

Once was to Columbia when I did not research the hotel properly and got a flea pit for a room and rain for 8 days straight. The other was a trip to Warsaw, Poland when I made the mistake of trying to take organized excursions and spent $800 getting scammed.


How was the trip to Argentina? It was one of the most amazing vacations I have had. With nothing planned, it became a daily highlight of surprises and joy. I just loved every second of it.

But, seriously, what a rush to play Travel roulette! To wake up in the morning and have no idea what country or continent you will be in that evening is just amazing.

Sure, it’s not for everyone. But it certainly is my idea of adrenaline journeys and adventure travel. I am a very spontaneous person, so I guess it fits my personality. I stopped doing it for a few years. Life and work and relationships got in the way.

Back to the old ways…

Recently, with a clear agenda of nothing planned, I did it again. I have been bitten by the bug once more! I had just finished a cruise in Paris and was planning to spend 10 days in the city.

By day 2, I was feeling restless. I decided to head off to the Orly airport (cheaper flights out of there) and off I went to the departure hall. I decided to go to Tel Aviv, Israel but no flights were available. I then tried to get flights on Marseilles and San Sebastian. 

Eventually, the chosen and available destination was Menorca, Balearic Islands, Spain. Great choice! 4.5 hours later I was traveling through the island of Menorca in a cab to a place called Playa Cala en Bosch.

Playa Cala en Bosch, Menorca, Spain


The resort was very family-oriented – mainly Brits, from what I could tell. The marina is beautiful and the beach stunning.

However, August, even late in the month, sees the crowds. I had an amazing time of rest, meeting some interesting people and just chilling out. The weather was great. It is a little expensive out there and the noise factor can be annoying. 

Kids get activities in the day and the loudspeaker from the marina echoes irritating calls of games and applause. That said, if you block it out, you can deal with the 10-1 pm toddler frivolities.

Later, in the evening, the adult fun starts. Live shows and bands blare into the night, so be warned. If you’re looking for solace, this ain’t the place. 

The beach was great but the crowds were there from the early morning until late afternoon.

My beach time was after lunch and towards the 3 pm mark when the beach crowds started to thin out. The sun was still high in the sky and tanning time was safer and just as good as in the morning.

I would finish up at the beach around 6 pm, go grab a shower and then head out for a bite at around 8 pm.

Evening in Playa Cala en Bosch is a good time for the pub crawler or to find someone just to  hang out with. A lot of the restaurants offered live entertainment which wasn’t bad. 

Suffice to say, I was happy overall with my choice of destination. I considered it another successful gamble in my own game of travel roulette. I will now, in my travels and work at Viking Cruises and for the benefit of my program directors blog, continue to follow this method. I love the surprise.

Meanwhile, for the curious, here’s some information on what happens to Viking River cruises when we all go “off-season” and on our travels or back home. We call it Winter Harbor a place we arrive to for season start..

So, how should you play Travel Roulette?
  •  First up, you need to have an open mind and not try this on a tight budget
  • Be sure that you do a little research at the airport when you see a destination on the board that appeals to you.
  • Check the 14-day forecast for weather.
  • Confirm that you have the correct documentation to have legal entry into the destination.


  • Don’t go someplace that is the opposite season to the clothing you have in your luggage
  • Be sure you can get a return flight at a date that works for youHave sufficient emergency funds for any rude surprises like expensive accommodation.
  • Don’t be afraid. You see it. You go for it.

That’s it! Surprise yourself and live a little on the edge. You will not regret it, I am sure of that.  

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2 thoughts on “Travel Roulette. A new spin on taking a vacation and making it exciting”

  1. Well, I don’t think I would have the guts to do that. I love travelling and seeing new stuff but I need to be organized. I would be terrified to just go somewhere without a plan. But kudos to you for doing it. Sound exciting. But not for me!

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