Baboon in South Africa

Why Travel Planning Can Be Dangerous

Derek Travel Tips & Advice 69 Comments

Travel Planning - Baboon in South Africa
Young, naïve, frightened and desperately trying to look brave, I walked out of Bangkok’s Don Muang Airport at midnight, my first time in Asia, my first time backpacking, my first time in such a foreign place. And apart from my flight to Thailand, I had chosen not to do any travel planning at all. So, there I stood, my courage starting to fade, wondering how I was going to find a hotel and why I hadn’t booked a room in advance.

I eventually found the official taxi stand, hopped into a taxi and, because I had no specific hotel or guesthouse address to give to the driver, told him to take me to Khao San Road, an area I had only heard about from a friend of a friend a week before I left home.

Once there, I stepped out into the street, wandered around for a few minutes, found a cheap hotel and paid for a room. Just like that the mystery of where I would sleep came to an end.

And as I started to nod off that night, I remember thinking, “Wow, that was easy.” I had flown around the planet, on my own, without a clue how to travel, and yet I survived. Not only did I survive, I managed to make it into this crazy city and find a hotel without any effort whatsoever. Suddenly, traveling seemed much easier than I had ever imagined, and upon making that realization, I relaxed and the fear disappeared.

To the Beaches of Cambodia

Travel Planning - Beach Sunset in SE Asia
Two weeks later, after having celebrated the Millennium at Angkor Wat in Cambodia, my plan was to spend a few days in the Cambodian capital of Phnom Penh before heading to Vietnam. But when I arrived in Phnom Penh, a British fellow I met convinced me to take a detour to Sihanoukville, Kampot and Kep, three Cambodian towns I had never heard of. Why not, I figured, and so I joined him and we ended up spending ten days hopping around from beach town to beach town, enjoying what was back then a very local Cambodian experience. We ate fresh fish, hiked through rainforests, rented motorbikes, visited random villages and met so many amazing people.

And while on the beach one day, I thought back to the moment I had arrived in Bangkok when I wished that I had planned my trip more thoroughly. Now I just chuckled to myself, happy as can be on a beach I just learned about and fully aware that such thorough travel planning would have been a major mistake…

From the Middle East to Thailand

Travel Planning - Sign in Iraqi Kurdistan
When I traveled through the Middle East a year and a half ago, I had a vague idea that I would spend a couple of weeks in Syria, a week in Lebanon, a week in Iraqi Kurdistan and then some time in Turkey. However, I didn’t dare book anything or make any concrete plans. And sure enough, upon arrival in the Syrian city of Aleppo, I found myself wanting to stay for a while. So I decided to stay for three weeks. I then traveled around the rest of Syria, followed by a couple of weeks in Lebanon, and then I returned to Aleppo where I spent another twenty days. From there I finally traveled to Iraqi Kurdistan, where, on my tenth and final day in that region, the snow started falling in the city of Dohuk and I suddenly had the urge to be in a warm climate. I turned on my laptop and immediately booked a one-way ticket to Thailand, deciding to skip out on Turkey this time around.

The next day I was on a flight to Bangkok, a destination on the other side of the world from where I originally thought I would end up. Imagine if I had already organized my trip to Turkey in advance. I’m sure it would have been a rewarding experience but I’m quite happy that I had the flexibility to follow my sudden desire to be elsewhere.

Extending My Stay in Romania

Travel Planning - Brasov, Romania
When I first visited Romania last year as part of my Eurail adventure, I found myself not wanting to leave, even though I had originally planned to visit Bulgaria as well. And since I hadn’t actually made any reservations or paid for anything in Bulgaria ahead of time, I was able to stay in Romania for as long as I felt like staying. Once again, nothing was stopping me from doing exactly what I wanted to do at that moment.

Flexibility, Flexibility, Flexibility!

Maybe you see what I’m getting at here. As tempting as it may be, you really don’t need to plan the details of your trip.

Had I already booked accommodation throughout Vietnam or had I booked transportation around Turkey or a flight out of Bulgaria, I would not have had the flexibility to change course and to ultimately end up with the experiences that most appealed to me at the time.

I can’t tell you how often my travels have changed. Actually, I can tell you. Every single time! Yes, every time I’ve gone anywhere my itinerary ends up looking nothing at all like the itinerary I imagined prior to my arrival.

Before we are actually present in a destination, there really is no way at all for us to know what will happen. The possibilities are endless. Sometimes we think we’ll love a place but when we actually show up we want to leave after one day. We might learn about new towns and cities and villages that we never knew about before and now we want to visit those places. We’ll meet new people all along the way, people we’ll want to spend time with, people we might want to tag along with to a region that we never thought about visiting. We might enjoy a particular destination so much that we want to stay for a month or we might discover a super-cheap airfare deal to a neighboring country and suddenly find ourselves wanting to go there straight away.

And when you do find yourself in such situations, you certainly want to be in a position where you can say ‘let’s go!’ and head off in that new direction, without any obstacles preventing you from changing course and enjoying these new experiences.

I know that it can be a bit scary having nothing, or very little, planned ahead of time before you embark on an extended journey. But in all my years of travel, I have never been without a place to sleep, never been without something to eat, never been stuck on the side of the road wishing that I had organized my trip in advance. What I have been is overjoyed time and time again at the fact that I’ve been able to alter my plans on a whim, to go places I never thought about going, to team up with new friends and to allow my travels to unfold on their own.


Do you agree that traveling is much easier than many people think? Do you plan much or do you prefer to go with the flow? If you’re about to travel, how much travel planning are you doing?

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Comments 69

  1. Pingback: What The Worst Golf Shot Teaches Us About Travel

  2. TJ

    I am planning a trip to Mexico for the summer, and am kind of doing what you did your first trip. I know where I am going but nothing else, I just want to see what I discover along the way, and don’t want to restrict myself. I had to put together some sort of loose plan for my family so they won’t freak out, but I doubt I will follow it anyway. Anyway thanks for the never-ending flow of useful information Earl!

    1. Wandering Earl

      Hey TJ – Have an excellent adventure and let me know when you leave as I might be in Mexico over the summer as well.

  3. Kate

    Hi Earl,

    I can really see the benifits of booking one way tickets but one of the issues I’m facing (I’m leaving for a 6 month-ish trip on June 2nd) is that I need to have my exit out of the country booked in order to get a visa. I’m arriving in Bali on June 4th and I had to book my flight to Singapore for July 3rd because I will only have a one month visa. What are your thoughts and how do you get around this?

    Thanks!

  4. Kevin

    Wow! I could have written this blog post. I agree with you exactly! My first big solo adventure last year to SE Asia, I planned nothing and LOVED the freedom it gave me! Saw so many great places and met so many cool people. Had I been more rigid, it would have only been 1/10th as fun!

  5. Rachel

    LOL, I did the opposite when I came to Thailand. Booked a hotel room for 3 months to make sure I had a place to stay then, of course, hated the place the first night and moved across Bangkok to another hotel/serviced apartment. Planned on staying a year at most. 10 years later……still here. Same apartment too 🙂

    1. Wandering Earl

      Hey Rachel – Ha…I love stories like this about how we plan one thing and something completely different and unexpected happens. That’s the power of travel!

  6. Pingback: Travel Itinerary: The Art of Unplanning

  7. Luisa Sousa

    Hi Earl and everyone adding so much to this discussion!

    I’m on the process of planing my RTW trip and the question that has been bugging me is the eternal debate over RTW tickets vs. buy-as-you go. I’m much more inclined to buy as I go, for one think that’s makes this trip exciting for me is the possibility of having the freedom to decide how long to stay in one place based on whatever I feel like at the moment, or choosing to go to some destiny that wasn’t planned because I met someone who said it was really cool.

    However, there are some practical aspect to this that I still haven’t quite figure out.

    The visas for instance. Don’t you have to indicate the date of arrival and date of departure in your visa application? How can you do that if you don’t know when you’ll be arriving or departing?

    Also most countries require you to have an onward ticket.. how do you by pass this Earl?
    Do you buy the tickets and then change the dates?

    I would love to know how you guys do it!

    1. Joel

      Luisa –

      My strong opinion after an 18 month RTW trip – buy as you go, without question. First off, our “one year” trip, turned into 18 months because we weren’t tied to an agenda. I had this same debate and am SOOOO glad we chose to wing it. I can also tell you that we tracked our spending meticulously (mostly to show others that it can be done fairly inexpensively), and I think the cost was equal or less in the end. Visas can be a pain occasionally, but not as often as you might think. And there is always a solution.

      As Earl has posted, planning is unnecessary and constricting. Our plans changed quite drastically from what we envisioned, often in a moment’s notice. We went places we never contemplated initially, stayed in place much longer than we thought we would, and never made it to others. With the flexibility of buy-as-you-go, you are guaranteed to have more impromptu adventures, that will probably be some of your best adventures. It is impossible to read up on all the different places and opportunities in advance and you will meet travelers that will tell you of a place you never considered. One of dozens of examples : we were in Bali and heard about these funeral rituals in Toraja, Sulawesi. We went on a whim and it was one of the most amazing experiences of our trip. Another time we ended up on a remote island in Indonesia that was just plain magical. We would plan days or even weeks in advance for certain things, like train tickets in India, but overall, not very much.

      Regarding visas and onward tickets. Any country that seemed strict about this just wants to see that you have an onward “ticket”. That doesn’t mean you have to actually honor it. We found a couple tricks. One – find a travel agent to book flights in and out, print an official looking itinerary, then cancel the itinerary. Then, just show that itinerary (if they ask) when applying for the visa. China and India were the only countries I remember even doing that. You will have a few visa challenges possibly, but it was well worth having that freedom!

      Joel

    2. Earl

      Hey Luisa – I always prefer the buy-as-you-go method myself. As for visas, it depends if you need to get visas ahead of time or you can obtain a visa upon arrival. If you must apply ahead of time, then you just need to give a date but they usually (with a few exceptions) don’t care if you actually arrive or leave on the dates you specified on the application. I’ve almost never arrived or departed on the same date I’ve indicated on a visa application and that’s never been an issue.

      As for an onward ticket, you can either follow the method I wrote about here: Proof of Onward Travel or you can just buy an fully refundable ticket and then, once you arrive, you can go online and get the refund. That’s generally what I do these days!

  8. Dan

    Earl, I used to travel exactly like you – didn’t make any reservation in advance. Especially when going with the car across Europe: I used to drive as much as I could every day, visit interesting locations and then find a nice hotel to sleep for the night. So each morning I never knew where I was going to end up sleeping each night.

    However as I learned more about traveling and prices I found that sometimes it’s better to book ahead of the time. It’s cheaper, and I also avoid being very tired and having to search for a hotel for 2 hours (there are towns in which you can’t find a hotel easily – such as Budapest, Varna, etc), or find that all the hotels are fully booked by others because of a concert in town (happened to me in Munich – happily I was with the car and found a hotel outside of Munich, but I had to drive for 1 hour and I was already dead tired from previous driving).

    Going online to search for hotels while in a new country is often not an option because of the 3G roaming charges – you can easily spend hundreads of euros.

    I will try airbnb.com instead of hotels – I prefer to support local families instead of large commercial organizations such as hotels or hotel chains.

    1. Earl

      Hey Dan – I think it is only cheaper if you stay in hotels as prices tend to fluctuate, while prices for hostels or guesthouses generally stay the same no matter when you book a bed/room. But yes, it is a good idea to check if there is a concert or any other kind of event so that you don’t end up somewhere that doesn’t have any rooms available!

  9. Belle

    Hi Earl,
    I have just found your website and been reading a blog and your post has really struck a nerve with me! I’m currently in the process of ‘planning’ my RTW travel adventure.. for some of the part i have booked organised tours which goes against my grain on so many ways (i’ve booked Nepal with a G/F on an organised tour) and Africa Overland for 73 days with an organised tour! I look forward to reading more of your posts as I’ve just subscribed! Belle
    http://www.travellingbelle.com

  10. Sam

    As usual, a great post. From the title I was expecting something about how doing too much research can lead to you wanting to go *everywhere*, but perhaps this says more about me than you! I really liked the little flashbacks in to your previous travel experience; if this were fiction, I’d say that it made for some great characterisation of this Earl guy!

    1. Earl

      Thanks Sam and I’m all for looking up places online and doing whatever it takes to ensure that desire to travel continues to grow! Research is quite beneficial in that sense. But actual planning is usually not needed…if I remember correctly, you didn’t have hotels reserved on your trip through Syria, right?

  11. Priyank

    Hi Earl,

    Good tips for slow travel although I don’t know what that’s like! People prepare for travels in a variety of ways; I prepare by reading books on history, archeology and art since those topics interest me and give a fair bit of idea about the country and the things I want to see. It seems I can learn languages quickly too, so all those things together are very helpful while travelling and make it very easy to plan-as-you-go even on few-weeks’ trips per year which is all I have. I usually book my return flight and nothing else, and it has always worked out excellent. 🙂

    cheers, Priyank

    1. Earl

      Hey Priyank – Reading up about a place is always a good idea as it does help when you know some of the history and what to expect ahead of time. But I’m glad you’re able to travel with so little planning even on shorter trips…that is the sign of a very open-minded, flexible traveler!

    1. Earl

      Hey Ava – Believe me, once you arrive in Bangkok, within two or three days, you’ll also realize that such travel is not scary at all!

  12. Amanda

    Up until this summer, I’d only ever done shorter trips – mostly around 2 weeks or less. With trips that short (and to destinations that can be popular and/or pricey), you often HAVE to plan ahead, simply because you don’t have time/money to waste.

    But, after traveling for 2 months around Europe this summer with an itinerary that has been more or less planned in advance, I can definitely agree with you that non-planning for longer trips is ideal! If I didn’t have to go back to school in a couple of weeks (and if I could afford it), I would absolutely continue traveling without plans. The freedom to do what you want when you want is definitely great, and I can’t wait to do a longer, more unplanned trip sometime in the future!

    1. Earl

      Hey Amanda – For shorter trips, absolutely, it makes sense to plan or else there would be a lot of wasted time. But for long-term travel, it’s quite the opposite as having that freedom is a key part of having a rewarding journey. Hope the rest of your trip went well!!

  13. Elle of Solo Female Nomad

    I am big on planning when I will only be in a certain area for a short time. In that case, I like to have my accomodation and transportation booked; especially if it is high season. When it is a long-haul trip I take alot of pleasure in being spontaneous, changing any plans I did make at a whim. Certainly, as a solo female traveler, I like to have the first nights accomodation booked.

  14. Andy

    I have thought about getting rid of the Lonely Planet or at least use it for quick reference or in emergencies only.

    What I found is that interacting with the locals is a great way to get the best deals on tasty restaurants and good accomodation and even some local sightseeing secrets that the traveling masses don’t know about. If you don’t speak the language there always be someone around who can help you out in english.

    Don’t let yourself be led around by the nose by your guide book or by tourist websites. It kills all the adventure and mystery that travel ought to be about. Thinking back the most amazing travel experiences came when I kept an open mind and went with the flow and the people I met. I my earlier travels I sometimes made the mistake of having a fixed idea in my head about what I wanted to see and do and while I did see and do all those things eventually, sometimes it felt like crossing tasks off a to-do-list like in a day job.

    A plane ticket and a room reservation for the first couple of nights is really all you need.
    Everything else will fall into place once you’re there.

    In travel, always keep an open flexible mind as much as possible. You’ll have much more fun that way!

    1. Earl

      Hey Andy – Exactly…guidebooks can be equally as dangerous as it becomes so easy to just follow the recommendations inside without ever finding information out on our own. There’s nothing wrong with having them, especially to learn about the history or things like that, but using them as the only source of travel information is not a good idea at all.

      Plane ticket and room reservation for a couple of nights is definitely more than sufficient!

  15. Audrey

    Many of our best experiences and travel decisions happened because we didn’t plan and had the flexibility to follow a whim or recommendation. That’s how we ended up in China for 3 months without planning to visit (but someone told us in Central Asia, “Go now before it’s all bulldozed” so we did) or in Burma in early 2008 (someone recommended it). Sometimes I think we take the “no planning” thing a bit too far 🙂

    My only suggestion with planning is when you are going during high season – like Colleen mentioned – as it helps to sort out something in advance so that you’re not stuck with only the most expensive options available. That’s happened to us a couple of times…not fun.

    1. Earl

      Hey Audrey – Definitely good advice about traveling in the high season to popular destinations….organizing some aspects of such a trip ahead of time makes perfect sense.

      And I do love how sometimes a lack of planning actually leads us to an entirely different country and completely alters our original plans. I’m sure you experienced it when you were in China, just standing there one day and it suddenly hits you that you are now in a location that you never imagined you would be in at that very point in time. When that happens to me, it’s smiles all around!

  16. Colleen

    One thing I would add on the topic of planning is this. If you are traveling anywhere in Europe during August, pre-booking lodging, at any price level, including camping, is highly advised. My family was bitten in the budget a few times during the summer there because in several cities and towns the cheap lodging and hostels were completely filled forcing us to into rooms double or triple what we normally spend. Actually August of 2009 found us sleeping overnight in the Dover ferry terminal for lack of rooms in town (those fill up fast with all the following morning ferry departures.) Also, we slept rough one night on the shadowy side of a municipal building’s lawn somewhere in France because I was not shelling $185.00 for a room. (I was having a moment of irascibility.) It was a cool experience, literally, and I’m glad we had it. Once. = )

    Europeans take the month of August to travel. This, surprisingly for Americans, often includes workers in the travel industry. Oftentimes a hotel or two in a given area will be completely closed for the month of August. Sometimes restaurants or shops are closed. And the campgrounds are packed.

    1. Earl

      Hey Colleen – Traveling during peak season is a different story and you’re right, in order to avoid paying high prices for accommodation, it can be a good idea to book ahead of time. Unless a person does want to sleep on the lawn of a municipal building more than once! I’ll pass on that!

  17. Steve C

    Another good post and question for comment Earl! First off, there are many very good comments by your followers above. I most concur with Colleen and Jeremy in the way I like to travel. Flexibility is the key to having the best long term travel. If your trip is less than a month, then you may want to plan it out a little closer.

    If you are “planning” a year or more to go around the world, I would never suggest a RTW ticket. In my 2 year RTW adventure, I found that when all was said and done, adding the cost up of all the one-way tickets was way cheaper than one RTW ticket, AND it allowed endless flexibility. Many times our next flight was determined by the deal we got on a ticket. We had a rough list of all the places we wanted to see but there was no particular order except what weather dictated.

    I also can confirm that in all my travels without prior reservations, I’ve always had a place to sleep, eat and a ticket to get there. And, the few times that I have made a hotel reservation, more times than not it ended up being a “one hour stand” type of place, if you know what I mean.

    The best suggestion I could give to those who are planning a long term RTW adventure is what you have written. Listen to seasoned travelers, as they have been there, done that. Stay completely flexible. You can’t know who or what is around the next corner, but you can place yourself to be there when it happens.

    1. Earl

      Hey Steve – I agree with you about the RTW flight tickets, especially when heading off on an extended journey. These days, I find that flights really aren’t that expensive, especially with all of the local budget airlines that now exist in every region of the world. And I just can’t imagine being locked into an itinerary because of pre-purchased flights. So many things can happen and as I mention in the post, it is almost a guarantee that a person’s plans will change. And like you said, considering that it really isn’t more expensive to purchase individual tickets throughout your trip, then a RTW ticket just doesn’t make sense any more.

  18. Chris

    Haha! Nice post. I nearly was going to sleep in a train station in Wellington earlier this year, only to meet a Mauri man on the street who ultimately invited us to his home. We stayed for three days, met his wife and kids, went to a local festival and ate Mauri food. By the time we left we felt like part of the family. One of the best experiences of the adventure.

    There have been times when I wished I had planned a least slightly more, but I’ve certainly encountered some amazing twists and turns that would never have happened with more planning. Here’s to adventure.

    1. Cindy

      I’m really glad to hear you were treated well in what I assume to be the NZ Wellington, such a cool city! (In which case, it’s spelt Māori – for future reference 🙂 )

    2. Earl

      Hey Chris – That sounds like a very cool turn of events in NZ…one minute you’re stuck without a place to stay and the next minute you’re having an unforgettable experience…the wonders of travel!

  19. Alex

    I only book the flight to the first country. If I did more than that, I know I’d be disappointed. In the last week, I’ve considered going from Israel and Egypt to more of Africa, to Thailand, India, Nepal, or to India, Malaysia, and Thailand… etc.

    I probably won’t really figure it out till I’m in Egypt. Who knows where the wind will take me.

    1. Earl

      Hey Alex – I like that style of travel…not knowing where you’ll be in a week from now and it could be any continent on the planet! Let me know where you do end up after Egypt!

  20. Will

    Hi Earl,

    It’s funny that you wrote this post as I am “planning” for my travels. I like to research areas with activities that I like to do. Then, (like you said) stay flexible because you never know when you are going to change your mind.

    It’s reassuring to hear that shelter, food, and transportation should be relatively easy to find. However, what about the sparsely populated islands in Indonesia?

    1. Earl

      Hey Will – I find that the sparsely populated areas are quite easy to travel around as there won’t be so many other tourists. You can simply show up somewhere, ask around for a place to stay and that’s about it. Of course, it’s often good to do some research so that you know you are heading to a region of the world or to a country that offers the kind of things that you enjoy, but beyond that, travel really is much easier than we think. I’d be surprised if you are ever stuck without a place to stay, even in the more remote islands of Indonesia!

  21. Emily in Chile

    I tend to plan a lot in terms of doing research beforehand just because I’ve found that it helps me enjoy a place if I have an idea of what there is to do. But I also try to stay flexible since it’s so true that some of the best travel experiences come up organically once you’re on the road.

    1. Earl

      Hey Emily – In the end, it certainly comes down to doing whatever we each feel most comfortable with and doing some research on your destination is of course worthwhile. It’s good to know what there is to do in each place and luckily we can find out that information without having to create a concrete itinerary.

  22. tyrhone

    Agreed, even in China, where I have found less english spoken than any other country I have been to, somehow things just work, as long as you think about what your doing, you can always get to your destination, find a place to sleep,eat, and generally be merry.

    My girlfriend is the planner of the 2 of us, but since traveling long term, even she has loosened the reigns, because every few weeks/days we change what we want to do, and it always seems to work out for the best. We went from a “planned” year in south east asia, to 4 months there, then China, and in a couple weeks…Chile! This travel thing is wanderful (excuse the pun).

    1. Earl

      Hey Tyrhone – That’s the thing, once you start traveling, you quickly realize that too much planning just isn’t necessary or worth it at all. Things do tend to work out for the best, especially if you stay positive. So you’re off to Chile…good choice indeed!

  23. Jeremy (TheTravelApprentice)

    Travel planning is a balance for me, I plan which cities I want to go but not necessarily how get to each place. I typically plan my first night because I like to have that sorted out but after that I wing it. That being said, I love planning… it gets me pumped for wherever I’m going but once you get out there traveling, everything becomes spontaneous anyways…

    1. Earl

      Hey Jeremy – I think doing research is always a good idea, at least a little anyway. And when I said ‘planning’ I was generally referring to the booking of accommodation, flights, buses or anything else that becomes finalized and set in stone before you actually arrive. That’s what can be dangerous in my opinion but choosing cities that interest you naturally makes sense, as long as you’re open to adding new destinations once you arrive!

    1. Earl

      Hey Ryan – Laziness works too as I’m sure you’ve always found a place to stay and eat during your travels. Keep staying lazy I say!

  24. The Travel Fool

    Great article Earl. On my extended trips I rarely have any concrete plans. It’s more a loose set of ideas on where I want to go and what to see. And like your article it tends to change quite often, but that is what makes the travel so fun. Having the flexibility to make changes or decisions on where to go on the fly. Sometimes I might meet someone that tells me about a place I had not heard of or festival occurring and all previous plans are out the window.

    1. Earl

      @The Travel Fool – I like that phrasing, ‘loose set of ideas’…that’s exactly what planning should be in my opinion! Much better than a concrete set of ideas!

  25. Globe Trotter

    I’m a female solo traveler. In all my travels, though I read up and do preparation, I have never pre booked an accommodation because all my flights are on standby basis and there can be occasions where I can’t get a seat to my destination.

    What I normally do is to check out a few accommodation options, get myself familiar on how I may find my way there from the airport. And, I just appear at the doorstep!

    When at the hotel, if they have a room for me, I then pull out my laptop to book online to get the cheaper internet rate. If they don’t, I walk around the vicinity which I have read up online in my preparation and walk around to find one.

    1. Earl

      @Globe Trotter – Thanks for that comment as it’s great to hear from a solo female traveler on this topic. Seems like you have a very good system in place by finding out information about your options but not confirming anything ahead of time. And that’s always a good tip about booking online even when you’re in the hotel lobby 🙂

  26. Earl from iPadNomads

    Ha ha,this post brought back memories of our arrival in Vietnam nearly 7 months ago to start our world trip. After spending so much time packing our things and preparing for our trip, we never got the chance to even look into Hanoi! We arrived just after 11pm with no clue of anything and took a taxi into town. My wife couldn’t believe I was able to actually fall asleep in the taxi even though we though we had no accommodation lined up!
    It ended up being the theme for most of our trip as we have now been to 22 countries and have only had places set up in a few cities before our arrival. Colombo, Sri Lanka was probably the hardest place to find something in our budget and late at night, but flexibility has been key for sure.
    We too stayed in Romania a few days longer than we planned and being flexible also meant not going to a place we wanted to go to because we didn’t have the time to fit it in with another place we wanted to see. While we have booked most of our major flights in advance, a majority of our time in a city is planned out when we arrived and we definitely have no regrets over the past 7 months.
    A lesson we learned early in our travels was that we weren’t going to see everything, so we weren’t going to stress out trying to see as much as we could but were going to experience everywhere we were!

    1. Earl

      Hey Earl – I think that’s what happens…the more you travel the less inclined you are to plan. But that’s funny about Vietnam! And it’s probably a good thing that happened as it showed you right from the beginning that there really wasn’t anything to worry about. You can always find a place to stay, although, your wife probably found the place to stay that night considering you were sound asleep in the taxi 🙂

  27. Paul Fuller

    I usually plan everything down to the last detail, which sometimes works in my favour but if you are somewhere where you know you will probably never be again then you may want to spend more time there or as little time as possible there. This happened to me when I was travelling around America with friends after uni last year. We booked everything down to the last detail and set ourselves times and dates to be in certain places and looking back in hindsight I think the trip would have been more relaxing if we didnt plan as much. A friend and I am booking a trip to Thailand to visit friends working there and we have no idea where in Thailand they will be posted or where they will be living so I think ‘the plan’ will be to just book flights and basically go with the flow on this one, therefore we will have no restrictions, no barriers and can enjoy our surroundings at our leisure. 🙂

    1. Earl

      Hey Paul – I’m quite sure that your plan (or your ‘non-plan’) for Thailand is going to work out very well in the end!

  28. Colleen

    In 2008/9 my teenage sons and I traveled for a year visiting 20 countries, 10 in SE Asia and 10 in North Africa, southern Europe and the Middle East. We never booked a room. Our approach was to arrive at a border or airport and begin. We used the LP and RG guides for each country. We’d just read up on the next country on the train, plane or bus there. We’d usually go with a recommendation from one of the guide books for our first night. If we didn’t really like a room that was shown to us at first, we might ask to see another or check out a different hotel down the street. We usually saw as many sites as we could fit into the day, except when we took a rest day where we did nothing except chill, read, eat and stroll the neighborhoods we were in. For long term travelers rest days are highly recommended. They recharge you and give you time to absorb, read and plan for your next week. Usually our rest days coincided with a particularly good room that made us say, “Hey, let’s cool our heels here for an extra day.”

    The entire world is overwhelmingly user friendly. You could be airdropped into the jungles of Papua New Guinea and probably some tribe would find you, put you in a hut, feed you and send you with a hug down the river the next day in a canoe to the first big town. People are kind, friendly, helpful and caring everywhere you go. Guide books make it easy to find lodging anywhere in any price category. We’re low-to-the-the-ground budget backpackers and that’s what we enjoy most. It puts you in closest contact with the culture. Same with street food. Eat like the locals. It’s fun, cheap and tasty. = )

    Bottom line: For anyone considering overseas travel for the first time, it’s easy. After a week on the road you will already have acquired 90% of the skills you need to travel anywhere. After a month, you’ll be a pro. You can do it!

    1. Earl

      Hey Colleen – You said it perfectly about learning the skills necessary after a week on the road. Almost every first-time traveler I know is shocked at how quickly it takes for them to become so very comfortable with every aspect of traveling in a foreign land. And you’re right about the friendliness of people and had me laughing at your description of being dropped into the jungles of PNG. We have this tendency to think that the world is dangerous or that strangers will always be out to get us when in reality, that’s very, very far from the truth!

  29. Melissa @ Suitcase and Heels

    I’m a self-confessed plan-a-holic. I really enjoy the planning part of a trip, thinking about all the things I could possibly do and places to go. Sometimes the anticipation is a small part of the fun of travel. I’m not a full-time traveller so my schedule needs to be a bit more fixed than some. I almost always book accommodations ahead of time and some attractions and tours but I like to try to leave my day to day itinerary free and easy. See what I feel like doing that day and go with it. Generally, if there’s a tour or attraction that I’d be disappointed to miss out on if it sold out, I’ll book in advance.

    1. Earl

      Hey Melissa – Haha…hopefully it felt good to confess 🙂 And I think it’s all different when a person is on a shorter trip that is not open-ended or several months in duration. It does make sense to organize and plan certain aspects on shorter trips in order to avoid wasting much of your day finding a place to sleep. Having the itinerary free each day is also the key as you never know what will happen or what you’ll discover when you walk out of the hotel each morning!

  30. Derek Hippler

    I think this is absolutely true for long-term travel, but I’d highly recommend the opposite for short vacations or people new to travel. If someone has a very limited amount of time to travel (a week or less), they lack the flexibility you mentioned and they might only find out about the best spots right when they’re about to leave. For people who are a bit nervous about travel, planning ahead can take the anxiety out of the trip by removing their Fear of the Unknown.

    – For long-term travelers, I think you’ve nailed it.
    – For short-term or nervous travelers, I think they’d benefit from some research and a list of things-to-see (though not an itemized itinerary; those are universally terrible).

    1. Earl

      Hey Derek – I agree about short-term travel for sure. Planning is quite wise in those situations. I was simply talking about long-term travel with this post as that’s what I know best!

  31. Christine

    As a woman traveling alone, I echo Gigi above; it’s most prudent to have a landing spot for the first night, and then I look for places the locals go (sort of like eating at truck stops stateside; that’s where all the trucks are, and those guys know where the good food is.). A trip to Thailand began as part of a group and after 1 day, I realized it was too “planned” and commercialized for my taste; lots of waiting around, side-shopping trip to jewelry store by the guide, eating “Americanized,” etc. So I loped off on my own w/out itinerary; had a blast.

    1. Earl

      Hey Christine – Having the first night or two planned is a good way to go as well. And then, once you’ve settled in, keep that itinerary open and see where the adventure leads!

  32. Christine Hayes

    Like Gigi, as a woman, I usually book my first night in a place and then play it by ear as I go forward. Where I am struggling now is planning my trip for the fall. There are some things I need to reserve, such as the Ayurveda retreat and the Vipasanna Meditation course (I am still on the fence about that), but what I am struggling with most are the plane tickets and dates. I plan to fly into India to Mumbai to Delhi and then need to get to Karala and back to Delhi, which aren’t a problem for dates, but after you tour I want to go to Mumbai, possibly fly to Almaty to see an old friend, back to Mumbai for the Vipasanna and onto UA ad Oman to see other friends before returning to Boston. I also want to be flexible to spend part of my friend’s holiday with him and travel elsewhere together. What do you recommend? I used to fly to a place on an open-ended ticket and then go with the flow until I was done and call to choose a date to fly back. It appears open-ended tickets are a thing of the past according to my recent research. Isn’t it a lot more expensive to buy separate tickets for each part of the journey? Thanks as always for your insight and information!

    Best,
    Christine

    1. Earl

      Hey Christine – It’s really not so expensive to buy several individual tickets, especially in regions that have many budget airline options. And luckily, India and the Middle East are two of those regions. I was just looking at random flights the other day and found one from Amritsar in Northern India to Dubai for $150 USD round-trip on IndiGo Airlines. That’s quite a deal. And flying within India is quite cheap too, especially between major cities. It’s common to fly between Mumbai and Delhi for $40 USD one way and even from Kerala to Delhi for around $60 USD.

  33. Gigi

    Yes! Having flexibility is so nice when you’re traveling. I would add the caveat that as a woman traveling alone, I always book one day in advance (before I left Rome for Tuscany, for example, I booked my first night at a hostel), just so that I know exactly where I’m going and if my train is late and I’m alone at night, I know I have a room.

    I also do book ahead a little more in more expensive places during their high tourist seasons. And now that I travel full-time while running a business, I book places a little farther ahead, just for peace of mind. (Though, honestly, not much peace of mind has come of it, now that I think of it, as last-minute cancellations have been the name of the game since I left the U.S. So perhaps I should stop trying to plan so far ahead!)

    1. Earl

      Hey Gigi – That seems more than reasonable to book that first night in advance. And there’s only one way to get rid of those last-minute cancellations…avoiding making the bookings altogether 🙂

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