TRAVEL STORIES · ADVENTURES & MISADVENTURES
Travel Roulette: A New Spin on Taking a Vacation
Taking a vacation anywhere 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 completely crazy and exciting experience!
By Rob Wheatley – Program Director & traveler
Originally published 13 October 2019
Travel roulette is my way of letting an airport departure board suggest the next adventure. It took me from a coffee-fuelled morning of indecision to Santiago, and later from Paris to Menorca. These are the stories behind the game, with a few practical checks before you try your own spin.
With 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 Fort 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?
The 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 the experience.
So, trying to settle on a location became stressful rather than enjoyable. 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.
Three 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 sort of plan going.
The departure board had other ideas
I looked up at the departure boards at Miami International 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 I worked my way through the later departures, the flights got more interesting.
Taking a blind leap of faith
I eventually settled on an evening flight. Chile! Santiago. 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. Travelling 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 Chile! Awesome. Forty minutes earlier, I’d 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 realised, 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 would get a day room near the airport and that way I could freshen up and sort myself out. I would text my girlfriend to let her know where I was going and I would try and find accommodation in Santiago.
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 somewhere to stay in Santiago. I found it. I booked it. I was sorted!
I 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 Chile. This was the beginning of my new pursuit of travel.
Eight and a half hours to somewhere new
The overnight flight out of Miami was an 8½-hour haul. I didn’t sleep much. I was too busy grinning at the seat-back map as our little plane icon crept down the continent toward a country I knew almost nothing about. I landed in Santiago the next day, tired, rumpled and thrilled, with no plan beyond a few travel tips. That was the whole point.
I checked in at the hotel, only to be told my room wasn’t ready. Fine by me. I asked where I should go for lunch, and the answer came back without hesitation: sopaipillas.
Sopaipillas, and a hill with a view
I dropped my bags and headed for Cerro San Cristóbal, the prominent hill that watches over the city. It has a cable car, a funicular, public pools and panoramic views that make you forget you’re running on four hours of airline sleep. I stood at the top and looked out over Santiago with the Andes standing behind it, and thought: this is exactly why I do this.
Then came lunch. Sopaipillas are really street food, and they are Santiago’s way of making “I’ll just have one” sound wildly optimistic. These little golden-orange discs get their colour from cooked pumpkin mixed into the dough, then head into hot oil until crisp outside and soft in the middle. They’re cheap enough to leave your sightseeing budget intact, although your shirt may not survive the toppings. Mustard, ketchup or pebre, a lively Chilean salsa of tomato, onion, garlic, coriander and chilli, turn each one into a small exercise in eating gracefully. Good luck with that.
When the weather turns cold or wet, look for sopaipillas pasadas. The same discs take a warm bath in unrefined cane-sugar syrup scented with cinnamon and orange peel. Suddenly, standing in the rain seems considerably less unreasonable.
But I digress.
Whatever the night had in store
I returned to the hotel that afternoon, and this time the room was ready. I had a two-hour nap, got up, showered and spruced up for a night of…whatever. Google told me to go to Bellavista if I wanted some nightlife action. I felt like it. I was buzzing. I loved the feel of the city and it had me feeling energetic.
Bellavista is the vibrant bohemian quarter, famous for its colourful street art, bars and nightlife. And I explored every part of it. Every. Single. Part. I made tons of friends along the way. I just didn’t remember a single one of them the next morning.
What I did have was a bracelet that did not belong to me, a note in Spanish that I couldn’t read, three new numbers on my phone and a blur of disjointed moments I could not piece together. Oh, and a pounding headache that would not let up.
A hungover visit to Palacio de La Moneda followed after a late brunch. I’m sure it’s a magnificent building. I mostly remember squinting at it. The afternoon dragged, and I eventually surrendered back at the hotel room, feeling and looking like I had been dragged through the bushes backwards.
I slept…
More roulette, a few misses
From 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 Colombia when I did not research the hotel properly and got a flea-pit for a room and rain for eight days straight. The other was a trip to Warsaw, Poland when I made the mistake of trying to take organised excursions and spent $800 getting scammed.
How was the trip to Chile? It was one of the most amazing vacations I have had, even with the headache. With nothing planned, it became a daily highlight of surprises and joy. I just loved every second of it (the ones I remember, anyway).
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…
On a later break in 2019, with a clear agenda of nothing planned, I did it again. I had 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 two, I was feeling restless. I decided to head off to Orly Airport to look for an affordable flight 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 to Marseille and San Sebastián.
Eventually, the chosen and available destination was Menorca, Balearic Islands, Spain. Great choice! Four and a half hours later, I was travelling through the island of Menorca in a cab to a place called Cala’n Bosch.
Cala’n Bosch, Menorca, Spain
Photographs from my 2019 Menorca trip.
The resort was very family-oriented – mainly Brits, from what I could tell. The marina was beautiful and the beach stunning.
However, August, even late in the month, brought the crowds. I had an amazing time of rest, meeting some interesting people and just chilling out. The weather was great. It was a little expensive out there, and the noise factor could be annoying.
Kids had activities during the day, and the loudspeaker from the marina echoed irritating calls of games and applause. That said, if you blocked it out, you could deal with the 10 am–1 pm toddler frivolities.
Later, in the evening, the adult fun started. Live shows and bands blared into the night, so be warned. If you’re looking for solace, this wasn’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 around the 3 pm mark when the beach crowds started to thin out. There was still plenty of daylight, and rather more room to enjoy the beach.
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 Cala’n Bosch was 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. It reminded me why I had started playing this game in the first place. 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 harbour, where we prepare for the season.
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 forecast for your travel dates.
- 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 you.
- Have 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 might love it. And if you don’t, you’ll at least have something to tell me.
Before you spin: a small word from the sensible department
I still love the idea of letting a departure board make a suggestion. Before you follow me into the terminal, though, a small word from the part of my brain that occasionally reads the small print.
Can you still buy a ticket at the airport?
Yes, some airlines sell tickets at airport counters—but a check-in desk is not automatically a booking office. Sales facilities, opening hours and payment methods vary. Take a working payment card and check with the airline; you may be directed to its website or app. In-person ticketing can carry an extra fee. American Airlines’ published fees, for example, include an airport-issued ticket charge for some journeys.
The departure board is not a promise
A flight on the screen may be full, too expensive or too close to departure to book and board. Don’t assume an unsold seat means a cheap last-minute bargain. And don’t confuse buying a new ticket with same-day standby, which generally operates under an airline’s rules for passengers with an existing booking.
Booking, check-in, baggage and boarding deadlines are separate, and vary by airline and airport. Leave several hours rather than planning a cinematic dash to the gate. Check the carrier’s actual cutoffs—these American Airlines requirements show why one universal deadline would be misleading. Include accommodation, transfers, baggage and the journey home in your budget.
“Visa-free” does not mean “just turn up”
Your passport, nationality, destination and any transit country decide the paperwork. You may need proof of onward or return travel, sufficient funds, or a visa or electronic authorisation approved before departure. Passport-validity rules also differ: six months is not a universal requirement.
The UK’s ETA guidance says to wait for approval before travelling; a decision can take up to three working days. Check US ESTA requirements too, where applicable. The EU’s ETIAS system is not currently operating; use its official website to check the latest position before a future trip. Our Visas & Entry Requirements guide explains the checks to make before committing.
Keep the surprise. Give it a fighting chance.
Try Skyscanner’s “Everywhere” search or Google Flights’ Explore map before leaving home, or over a coffee in the airport lobby. Look for departures you can realistically catch, then confirm the final fare, availability and booking directly with the airline. Search results are possibilities, not boarding passes.
Domestic travel—or destinations for which your entry paperwork is already sorted—can make the game easier. Set a spending limit, check that you can get home when you need to, and be willing to walk away.
Surprise yourself with the destination. Try not to surprise yourself at immigration.
Fancy a smaller spin?
If an unplanned flight feels a little ambitious, try a microadventure closer to home. Or browse more stories from my travels.
Where would your departure board take you?
Have you ever booked a trip on a whim—or stood in an airport wishing you could? Tell me where you ended up, or which destination you’d choose. Share your spin in the comments below.
Keep exploring
A little inspiration for your next unexpected turn.
The World Travel Course
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2 Responses
Awesome post! Keep up the great work! 🙂
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!