The 5 Most Challenging Destinations I’ve Ever Visited

Today’s Blogger in the Spotlight is Jason, the cool dude we all know as @digidrift and he is one of the more experienced travellers I know. This guy has covered over 90 countries during his travels and we feel so privileged to have him write about the most challenging destinations he has ever visited. Be prepared to be wow-ed!

When Ciki approached me to write a guest post on five of the most challenging destinations I’d visited during the past 20 years. I thought to myself, ‘this should be quite easy’. The more I delved into the topic, the harder it got for me to accurately portray what challenging really meant to myself, as well as communicating this to the reader.

As travelers we are faced with an array of small challenges each and every day. I believe the sum of all these challenges are in some way proportional to the budget one is trying to achieve during their travels. From my experience, it seems the further you are trying to stretch your dollar, ringgit, baht or euro, the greater the challenges, or the higher the hurdles that will be put before you.

“the sum of all these challenges are in some way proportional to the budget one is trying to achieve during their travels..”

It’s not surprising that most of the destinations listed below, were countries that I traveled as part of my five year non stop odyssey of traveling the world in my early twenties. Although I’ve continued to travel the world extensively, for another fifteen years since this initial voyage. The challenges have gotten a little less, with the more experience I have obtained throughout the years, and the more disposable income that I’ve had available for each trip.

I suppose travel is like any other task or skill, it is learned and refined through many years of experience. Without these experiences people will generally find it harder to deal with the day to day situations that travel, and especially independent budget travel will throw at you. Oh well, here goes…

1 – United States of America: It’s Not Easy Being Green

The thought of the good old US of A, being a challenging travel destination to someone who’s been to over half the countries on earth obviously seems quite odd. Let me tell you, for a green young 22 year old, without any travel experience, it did throw up a fair amount of day to day headaches.

On arrival in Seattle back in 1992, I had no idea on where I was going. I knew nothing of guide books, public transport, budget accommodation. Let’s face it, I knew nothing. I was on my own, and to be quite honest I was completely clueless on what the hell I was doing. It seemed that every single daily task was a challenge, and quite a steep learning curve.

I believe one of the biggest things that the young backpacker of today takes for granted is information, and it’s ease of availability. Before I left for America, I’d never met anyone who’d traveled before, none of my friends had been overseas, and travel was in no way as common as what it is today. The biggest reason I found it a challenge was I basically had no idea what I was doing, and no quick way of learning.

“one of the biggest things that the young backpacker of today takes for granted is information, and its ease of availability..”

In reality it was the best way for me to establish the skills of independent travel, and the number one challenge I faced was definetly budget. The way I was spending in the first few weeks after leaving home, I would have been home for Christmas.

I was slowly working through these issues, and then I met Carl from Liverpool England. From that point on I was given a true lesson in the art of budget travel. Everybody has to start somewhere, and for me that was the USA, and my first month or so on the road was quite a challenging time.

2 – Zaire: The Challenge of Finding A Meal (and paying for it)

Zaire, or now known as the Democratic Republic of the Congo, was a county on the brink of civil war when I first visited in 1993. The country was a complete basket case, in every aspect. Everything was a headache, and just finding something to eat during this time was a challenge.

Trying to look after your health was always an issue in Zaire, and I found myself living on pineapples, boiled eggs and bread for 3 meals a day. It was keeping me alive, but was a real mental challenge to deal with day after day. I used to joke with a couple of fellow travelers, that there was only so many ways you can slice a pineapple.

“I found myself living on pineapples, boiled eggs and bread for 3 meals a day..”

Another gigantic challenge I also faced in Zaire was money. Hard Currency was obviously king, as the local currency had inflation running at a ridiculous rate, seeing the local Zairean valued at 5.5 million to the US dollar. Finding someone trustworthy and reliable on the black market to change the currency was a big headache, and the bank was out of the question. During my time in Zaire, the banks had no money in them, I mean nothing, not a single dollar.

Once you found someone on the street to change your money, the next problem was the minuscule size of the denominations of the bills. The largest banknote during my travels in Zaire was the 5 million note. It was worth less than 90 cents at the time I was in the country, and was considered worthless in the eastern part of the country. No one would accept it, as rumors were flying around that it was a counterfeit.

Having to carry hundreds of millions in Zaire’s on your person, was also an issue. Due to the sheer physical size of the bills, they couldn’t be hidden in a wallet. You basically had to carry all of your cash in your daypack due to its size. As you can imagine, in a country as hostile as Zaire at the time, this was far from ideal.

Zaire was a complete struggle and a huge challenge every single day, both a physically and mentally. I suppose that’s why it does grant me some of my most fondest travel memories.

3 – Morocco: Patience In a Land of Frustration and Hassle

Morocco was a challenge right from the moment I stepped of the ferry from Gibraltar, and boarded the train to Tangier’s. Everywhere we went, the touts and hawkers would drive us insane. Always wanting to be our guide, or supply us with some service that we didn’t want or need.

I remember reading the Lonely Planet Moroccan edition many years ago, and it made mention of the fact that it was near impossible to find your way out of the old souk of Fez without having to pay (and let me stress the word PAY!) for a guide. Although we got completely lost on several occasions paying some exorbitant fee to some dodgy tout, to help us escape the maze of tight alleys and lane ways was not going to happen. They were continually at us, every minute and making it hard to concentrate on where you were going (a tactic on their behalf, no doubt).

I remember vividly the touts following us through the streets and alleys, laughing and pointing, but it was us who had the last laugh. We did find our way out, and we would not be stood over by such extreme tactics. Dealing with these types was a constant hassle in Morocco, and one that would continue to grind you down, if you let it.

Although Morocco is a beautiful country, and the general person you met on the street was more than helpful. The touts and hawkers were just ridiculous, and completely relentless in trying to extort money from you. For this reason, I found Morocco to be extremely challenging.

4 – Iran: The Language and Cultural Barrier Challenged Me Daily

I visited Iran back in 1995, and I found this destination a challenge due mainly to the language and cultural barriers that existed. On this trip I was travelling with my partner Liza. As an unmarried couple traveling together, it made for some difficult moments. I could not talk to women, and men would direct their questions for Liza through myself, so meeting people was quite difficult.

Catching public transportation together was also an challenge, as men could not sit next to women. We always seemed to work it out, but there were always a few issues along the way. Although we are not married, the wearing of wedding bands did help us on many occasions.

“although we are not married, the wearing of wedding bands did help us on many occasions..”

One of our most challenging times in Iran, was the day we arrived just after dawn at the main bus terminal in Tehran. There weren’t many people around, and we couldn’t read a single sign, to gain our bearings. We ended up walking seven kilometers with heavy packs, all the way into town using the slowly rising sun to gauge our direction, and guide us to our hotel. We got there in the end, but it was a tough morning, with the lonely planet maps saving our hide once again.

Iran has been one of my highlights from twenty years of travel, to almost 100 countries. Although a challenging destination at times, the warmth of the people made up for the day to day cultural issues faced by an unmarried couple.

5 – Cuba: Once There, The Challenge Was Traveling On A Budget

Cuba was a challenge in a number of ways. I visited with a good friend of mine back in 1999 and the first challenge we faced, was actually getting there from Australia. With Australia being a large but isolated country, most of the direct flights heading East, went through the US (where you could not obviously fly to Cuba). We ended up going through Mexico and Jamaica, and it was an extremely expensive, and lengthy flight.

Once in the country there were a number of issues that confronted us on a daily basis. One of the biggest challenges faced was the exchange of Currency. I’m not sure what it’s like today, but back in the nineties there were actually three currencies in operation within Cuba.

“eating in cheap restaurants was not always the best thing, and I did find myself eating dog in Cuba..”

There was the National Peso, the Convertible Peso and on top of that, the US Dollar was also excepted on the black market for various goods and services. The National Peso was the currency any budget traveler wanted to get there hands on. This would then enable you to pay for things at the local rate, which was extremely cheap. Although eating in cheap restaurants was not always the best thing, and I did find myself eating dog in Cuba (my Spanish wasn’t the best and I had no idea what ‘el perro’ meant).

The challenge was actually finding someone to change your money as currency exchange was highly illegal, and Cuba was not known for their liberal court system. On top of this, you needed to make sure you didn’t change too much, as once changed it, it was guaranteed there’d be no one willing to change the currency back.

We got caught out by this, and in the end had quite allot of National Peso’s left over. I remember vividly the last day before flying out to Jamaica, spending a very large sum of National Peso’s at a Chinese restaurant on lobster and crab, but still couldn’t burn through the money left over. On leaving, our waiter got a hefty tip, and lobster certainly tasted better than dog.

Cuba was challenging, but I believe that every year since then it would have gotten easier as the systems become more tourist friendly, and it begins to fully open the doors to commercial tourism.


About this week’s Guest writer:

Jason has traveled the world extensively during the past 20 years, with overland journeys on 6 continents and across over 90 countries. Travel is somewhat of an addiction to him, as he shares his experiences and thoughts through his blog. The site also features some stunning photography, as well as other information that the independent world traveler would find of interest.
Read more about Jason’s travels and adventures on his blog
Follow Jason on twitter @digidrift


  • Nisha says:

    Very informative and a kind of eye opener post. Didn’t know that Zaire would be so difficult.

    And I thought wearing a wedding ring is a passe now though being married I always wear one. 🙂

    • Jason says:

      Hi Nisha, Yes I can certainly say that Zaire was quite the challenge, but looking back it also gives me some of my most fondest travel memories.

      The wearing of wedding bands in Iran was something Liza (my partner) had read about. The Islamic Revolution was certainly underway when we were in the country. Liza had to wear the full Chador, and I had to wear long pants and long sleeves, regardless of the temperature.

      There’s one thing I can say about Iran, and that’s how well we were treated.

  • Carolyn says:

    You have had some unbelievable experinces! Regarding to the wedding rings, my boyfriend and I taught in South Korea a few years ago and since we lived together our schools not so subtly hinted that it would be easier if we said we were married. We are accustomed to such a liberal lifestyle in Canada that we sometimes forget how conservative other cultures can be. Also, you wouldn’t mistakenly eat dog in Korea since it’s actually more expensive than other meats!

    • Jason says:

      Hi Carolyn, Yes there’s certainly a few memories there. The wedding rings did certainly help, in some circumstances. It also just made it easier than trying to explain our situation, or telling people she was my sister. I didn’t like making up stories, but if we didn’t then we weren’t able to find accommodation together.

      In relation to the eating of dog, I’m not one to judge other cultures, and each to their own I say. It’s just that a dog to myself, is like a cow to a Hindu. I love dogs, and I wish it could have been any other animal but dog. It felt quite strange after I found out what I had eaten.

  • Sean says:

    yikes! zaire does sound like it would be an absolute nightmare for most of us who long for leisure and fun during our travels abroad! lotsa respect to you for doing that! 😀

    • Jason says:

      Hey Sean, Yes Zaire was an absolute nightmare when I visited. Completely insane would be more like it, but that’s why I loved it so much. At the time, things were quite difficult, with the shops having no food as the economy was in turmoil.

      The army hadn’t been paid in months and were resorting to extorting money from people at bridge crossings and road blocks.

      At these road blocks, I and some fellow travelers were then forced to throw wads of cash into a bag before we could cross. As the white fella’s on the truck I was hitching on, they always demanded allot more from me, but then again who’s going to argue with a drunken Zairean soldier at 9.00am in the morning, and holding an AK47.

  • Isaac Tan says:

    Such an interesting writeup. will be reading it again once i’m off work, to fully digest every detail!

  • About time you featured Jason! One of the few “real” traveler types out there.

    There’s a difference in reading about Jason’s travels than many other peoples. I would certainly encourage one to go out there and have a read about his travels.

    • Jason says:

      Hey Dave, Thanks for the support mate. I do feel I’ve seen and done a bit in my time and that I do have a bit to offer the travel community. I do agree with you on what so many people are writing about on travel blogs these days. It does seem to be the same stuff over and over.

      I suppose everybody’s got to start somewhere, but it’s a big world out there and I just hope people can stray of that beaten path a little.

      I suppose, long term travelers such as yourself and a hand full of others, will need to keep flying that flag for a little longer yet.

  • Juno says:

    This is very inspiring post. Travel is challenging no matter where you go, but it’s true some places are more challenging than others.

  • Jason says:

    Hi Juno, Yes travel can certainly be challenging at times, but everyone is challenged in different ways. I suppose I enjoy the challenges travel has put before me, and that’s why I keep going back for more year after year. Like most of us, just another travel junkie looking for my next fix.

  • Leigh says:

    Love the post Jason. I’d read about your Morocco travels before but interesting to see the other countries that presented obstacles. Wonder with all your travel experience now if you’d have the same issues with Iran & Zaire. You have been to some very unusual places.

    • Jason says:

      Hi Leigh, Interesting point you make, and after a bit of thought I would say that both would be only slighty easier. If I were traveling in Iran on my own then it would be much easier, but the cultural issues of traveling with my partner Liza was where the biggest challenges were thrown up.

      On Zaire/DR Congo, I feel I’ve gained plenty of experience traveling over the years preceeding the first trip to this country, and this experience would help. Saying that though, the DR Congo would have to be one of the most difficult places still in the world to travel, and as I’ve heard it put before ‘It’s more a geographical concept, than a country’. It would be extremely interesting to get back there one day.

  • Loved this post! I’ve never been to any of these countries (except my homeland, the US) but I could relate to your experiences. I know what it’s like to fend off zealous touts when you are determined to stay on a tight backpacking budget. Did you end up staying with your girlfriend after your trip to Iran? I traveled RTW with my fiancee for 12 months and we ended up getting married 🙂 Anyway, great post and I look forward to reading about your adventures on your blog.

    • Jason says:

      Hi Leslie, Yes those touts can sure get anoying at times, and did push my paitence to the limit. Yes I am still with my girlfreind after all these years, and we have continued to travel the world together.

      I feel traveling is one of the best tests for any long term relationship. Becuase travel can get quite stressful at times, it is interesting to see how each person reacts to these situations. When we travel together we are sort of like a well oiled machine. Each knowing what to do in certain situations.

  • Apple says:

    I really enjoy reading your travel blog. You are one lucky fella, thanks for the sharing.

    • Jason says:

      Hi Apple, Thnaks for that, and thanks for reading this guest post. I suppose I am lucky in a sense.

  • Really enjoyed your insights into each of these places…I agree whole heartedly about Cuba – I wanted so much to enjoy the sum total of the travel experience there, but I found it quite difficult to stay budget, find good food, and locals willing to talk and share!

    • Jason says:

      Hi Shannon, Yes Cuba was an interesting one. I did find that people were very reluctant to open up, and I suppose as the country slowly transforms this will fade.

      As you found out, it was quite hard to travel on a budget and the two tiered currency system made it extremely difficult to get around. I would love to return to see if there has been any change made.

  • Caroline says:

    what an adventure! i love this post a lot! very informative indeed! 😀

    • Jason says:

      Hi Caroline, Yes my traveling life as been full of adventure, and hopefully will continue. Glad you enjoyed the post.

  • So one may dine on canines both in Cuba and in China… interesting coincidence… And I feel so undertravelled now! 😛

    • Jason says:

      Hi Kenny, Yes it seems to be the case. I did some research into this and it apears that it was only during a short time in the ninties when there were food shortages going on in the country. I’d be interested if anyone else has come accorss it.

  • cumi&ciki says:

    This is truly and inspiring post. Jason, when you asked me to edit it as I saw fit.. it really was impossible to remove any bit of information because your experiences with each country, and the take home messages have great value. Thanks for sharing such an indepth post! Much obliged;)


    • Jason says:

      Hi Ciki, Thanks for the oportunity to share some of my adventures on your blog. I enjoyed writing the post, and responding to the comments. Your very welcome……

      Safe Travels


  • Neil Fahey says:

    Try going to Cuba as a vegetarian!

    • Jason says:

      Hi Neil, I couln’t imagine it. It must have been tough, although it was quite a shock to me after I found out what I had eaten. I suppose it would be like a strict vegetarian finding out they had consumed meat.

  • Great info Jason, thanks for sharing. When I first arrived in US from Malaysia, I had some trouble adjusting to the lifestyle and culture. Sometime Google is not the answer to everything 🙂

    • Jason says:

      Hey Kiran, There’s always and adjustment period when ever you enter a new country or culture. No matter how many times I go away, I always have to adjust. Not quite sure where your heading with the Google comment?

  • Sarah Wu says:

    wow very inspiring. It’s insane too (in a good way). 90 countries? I can’t visit 90 countries. I need to save now for a wedding of my dream lol. Maybe after wedding I’ll see how I can I ever achieve that, maybe never.

    • Jason says:

      Hey Sarah, I am by no means a rich man, and have just basically dedicated every cent I could spare over the years to feed my travel addiction.

      I’m glad my post was inspiring to you, and never say never. If you want something bad enough you will find a way. Good luck and Safe Travels…

Leave a Reply

Your email address will not be published. Required fields are marked *