Practical Logistics For Extended Travelling

Filed Under: Advice, Travel

Last summer I finished a contract role at work, packed a suitcase and headed off on a long summer vacation following the sun. It ended up lasting for exactly 100 days, where I managed to visit 20 different countries across Europe, the Middle East and Asia.

Had the finances not run out, I could have easily kept traveling for another month or two.

It did take some adjusting to pack up all my things every few days and move on to a new city or country. But the traveling life quickly became real life and to be honest I sort of forgot about my responsibilities back at home.

You might be dreaming of a gap-year backpacking through Southeast Asia, or a working holiday through Central America, or maybe even volunteering in Africa for an extended period of time. There are some logistics to traveling long term that you might not realise as you are planning or packing for a trip. But if you are planning on taking a long trip, consider these before you leave!

The European part of my 100 day trip

Pack as light as possible

This is probably the most obvious, but also the most important.

I guarantee you will not be glad you brought that fifth pair of shoes with you, as you lug your suitcase up the 50th flight of stairs on the trip.

If you can’t easily carry your luggage up a flight of stairs, you have brought too much.

Rollaboard suitcases are wonderful for the smooth polished floors of major airports, but you will be cursing them as you try and drag them through a cobbled street in Rome or up a narrow and steep staircase in Amsterdam.

I’ve written separately about the benefits of traveling with hand luggage only — it makes life so much easier.


This was by far the most frustrating part of the trip, and I have always wondered how Ben manages this long term! The lighter you travel the more often you will have to wash your clothes. I can’t bring myself to pay hotel prices for laundry where it can be $5 just to wash one shirt. So I would ensure that at least one night per week was spent either at an Airbnb, or at a friend’s place with a washing machine, and I’d take an hour or two out of my week to wash my clothes.

Smart, experienced Airbnb hosts will provide washing liquid/powder, because it is an absolute pain to have to go out and purchase this each time, and I didn’t really want to carry around small bags of white powder through airports!

Fortunately as we were following the sunshine our clothes air dried quickly (I don’t trust tumble driers, especially ones I haven’t used before), and there is an odd sense of accomplishment and replenishment knowing all of your clothes are clean. Or maybe I’m just OCD?

Don’t plan everything

I am a bit of a control freak in planning travel though learned to relax quite a bit on this trip. For the final four weeks we did something I had never done before, which was not plan anything in advance. The weather in Southern Europe by September was starting to be a bit unpredictable, so there was little point booking a week on a Greek island if rain was forecast.

It was really exciting as we went into the shoulder season at the end of summer, as there were loads of cheap transportation and accommodation options when booking last minute. It meant visiting places I had never heard of or ever planned to go.

We ended up spending a week in Ksamil on the very southern tip of Albania, because we stumbled across the best beach I had seen in Europe.

We would never have found Ksamil in Albania if we had planned everything in advance

Have perspective when something goes wrong

We were lucky on this trip, that other than some unfortunate weather resulting in several days inside, there were no major hiccups. But on a previous five week Europe trip a few years back, within just a few weeks I managed to:

  • Be without my luggage for the entire time I was in Iceland (thanks Turkish Airlines!);
  • Find my accommodation in Serbia did not have any running water for five days in 35 degree heat, which led to:
  • Developing an eye infection in Turkey; and
  • Having my mobile phone stolen at the same time.

The frustrating part about bad things happening when you are on the other side of the world is that you are less powerful to resolve them than you would be at home. You can’t go down to your local doctor to resolve it quickly and easily –- visiting an eye doctor in Istanbul was not an experience I would want to repeat regularly! I kept saying to myself over and over, ‘if I was just at home for one day I could fix all this.

But of course, you are not.

And you shouldn’t throw in the towel for the whole trip because something isn’t working out, because if you do you will resolve everything in one day and then wish you were back on the trip. I kept telling myself these were all temporary inconveniences that would resolve themselves. And sure enough:

  • My luggage was eventually returned to me;
  • I had running water as soon as I left Serbia;
  • My eye healed; and
  • I survived without a phone for a few weeks!

Resilience is difficult to teach, it needs to be experienced. Just try and remember what is more important and that life will go on.

Take ‘time off’ from the holiday regularly

This is always the tip that requires the most explanation to people. No matter how much you are enjoying the break, particularly if it’s a very active holiday and you are traveling with just one other person, you may need a break from all the activity, and perhaps even from each other. You don’t need to ‘do something’ every single day even if that something is lying on the beach in the sun.

I always try and take one day every fortnight where I do absolutely nothing and not feel guilty about it. If it’s raining that’s always a great day to do it. Stay inside, read a book, watch a movie, have a nap, and have some ‘you time.’

You might feel you are missing out by not seeing every single thing in every single place you visit, but trust me, it will preserve your sanity.

Even on holiday, you need to look after yourself.

Mix up your activities

I couldn’t have had only one ‘type’ of holiday for 100 days.  I would go mad with the boredom/repetitiveness.

Sure, I could have had a $1,000 per night overwater bungalow at the Conrad Rangali in the Maldives with endless room service and day spas, but after a week I would have been ready to do something different. Equally I can’t do walking tours around a big city for 10 cities in a row.

Where possible, mix up your activities. If you’re sick of lying on the beach, explore a nearby town. Feeling overwhelmed by a city? Do a day trip out in the countryside. If you’re sick of the cold weather see if you can do a side-trip skiing somewhere. It can get boring doing nothing believe it or not. After a week of lying on the beautiful sleepy beaches of Ksamil, Albania, it was wonderful to catch the ferry over to the Greek island of Corfu and explore the bustling old fort town.


This is one of the last things you’ll feel like doing but one of the most important. I found going for a run or long walk as soon as I woke up was the only time each day I found the time and energy to do regular exercise. Jogging through the back streets of Bosnia did receive some odd stares, but it felt like I earned that afternoon beer that would call my name as soon as the sun started to set!

I also try and have at least one alcohol-free day each week. This was harder than it sounds because it wasn’t like I had work the next day.

Logistics back home

Life will go on back home. Bills will be due, mail will be sent to you, errands will still be required. Obviously move as much of your physical mail online as you can. It’s also a great help if you have loved ones back home that can occasionally help out by checking on your property, opening/sending you your mail and even helping with the odd errand. You can certainly bring them back some souvenirs in gratitude.

Don’t forget to pay your bills on time — they will not accept ‘I was on a really long holiday’ as an excuse for not paying on time.

Bottom line

Ben often talks about his ‘ultimate first world problems.’ And I admit sometimes I laugh when he notes something like the small size of his on-board shower, or the less-than-stellar year of his vintage champagne.

Equally I’m sure some of you will laugh at the idea that anyone would need some sort of advice guide for how to cope with an extended holiday, other than to ‘relax, do what you want and enjoy.’ But if you are fortunate enough to travel for an extended time (and I do thoroughly recommend it!), it’s important for your sanity and well-being to look after yourself.

Do you have any tips for long-term traveling?

  1. Thank you for this article, James. Leaving next week for a two month trip around the world. Your article offers good perspective. I will definitely be heeding some of your advice.

  2. Kudos..have to admit..a very good written report!

    One step at a time and you will convert every stubborn Lucky supporter here and how good you are evolving..

    Could not believe I am praising you right now..probably hell has frozen!
    Just a joke! ..keep the good reports coming..

  3. Another tip would possibly not to squeeze in that many places in the span of 100 days? I’m not sure if that gives you enough time to get the proper feel of each place you visit.

    If anything, you could learn more on slightly longer stays on each trip…like the fact that countries with Orthodox Christian populations usually have their Christmas on January 6th or 7th 😉

  4. Can’t stress “do not plan everything” enough. As a matter of fact – plan only the necessities. The best perk of an extended trip is that time is on your side. Talk to people (locals, ex-pats, other travelers), and you will find out everything you need to see and how to get there. This is much more useful than TripAdvisor. It’s also a much more relaxing way to go about things because when plans don’t go the way you want, all it does is cause stress.

  5. I took a long trip last year and one of the things I had to figure out, but which was most fun, was how to get my hair cut a few times while I was gone. I know most people would just let it grow, but long hair drives me nuts, and to me it was part of the fun to see how it’s done elsewhere, so I researched how to make it happen. It was not as easy as you’d think, but it all worked out and made for a fun adventure.

  6. @ Julia – some of the countries/cities I had visited before, and was only visiting for a specific event, so didn’t feel the need to spend more than a few days there.
    Others had poor weather so I moved on after a few days to better weather.
    Some were really expensive destinations, so would have cut the trip short had I spent a long time there.
    I spent 18 days in Italy on this trip so learnt plenty there ; )

  7. Great article. Despite my nits every so often, I ‘m really enjoying your articles and the perspective you bring. Cheers!

  8. @ James:
    How about avoiding to “carry around small bags of white powder through airports” by using laundry detergent tablets/pods?

  9. James, thank you for this article – and overall all the fantastic content you have been bringing so far. It is very refreshing and you do have great writing skills :)!
    Like you, I have a tendency to over organize trips when I go somewhere, mostly out of fear that if I wait last minute, hotels will be sold out or too expensive, and I’ll just end up worrying about it. Do you have any perspective on that?

  10. Your comment about not carrying white powder in airports, brought back the memory of an arrival luggage search in Tokyo. The passengers stuck waiting in line behind me and my wife let out a collective gasp as the inspector, elbow deep in our checked luggage, pulled out a 1kg bag of salt we had purchased in Thailand.

  11. @ Frank – I always worry those pods will burst in my luggage given they disintegrate even in cold water!

  12. Ben this is a great post, but many of us are worried that you are going to get burned out with all the writing you’ve been doing. You’re posting almost as much content as Lucky.

  13. @ Chip Douglas – I appreciate your concern but honestly, I’m only writing one post a day while Ben manages 7+.

    It only takes me an hour or two per post nowadays and honestly, opening the laptop, pouring a glass of wine, putting on some music and just writing is probably my favourite part of the day. I find it very relaxing.

  14. Great article! We did 3 months in Tokyo and definitely learned a bunch of these the hard way. Like ConEd (NYC’s power company) won’t let you log in from another country to pay your bill. Even with a VPN it didn’t work. We ended up doing a Remote Desktop screenshare with a computer back on my desk in the US to log in and pay our bills.

    Another big thing I learned is that it’s next to impossible to buy shoes or clothes of any sort when you’re 6’1 240# in Japan. I ended up bringing a big suitcase full of emergency/special occasion clothes and shoes and stashed it in a friend’s stairwell in Tokyo when we were out exploring different parts of the country.

  15. Nice article, James. I did 35 countries last year and as I write this am leaving Central America for the South Pacific. May I add:

    • consolidate everything into one light carry-on bag such as eBags weekender
    • 8kg max; you can buy stuff literally everywhere, that includes Africa
    • an ultralight down jacket is also great for sleeping on chilly flights and can be rolled into an ultra lightweight stuff sac and used as a pillow if somehow necessary
    • when your Airbnb doesn’t have laundry facilities you can usually get 2kg of laundry done cheaply in town somewhere; waste of time to do it yourself as the savings is minimal
    • don’t ever check luggage; repeat

    You can rent bicycles, scuba gear, climbing equipment etc literally everywhere these days … so I say why take stuff that potentially can get lost or stolen … not worth it if you’re globetrotting

  16. Speaking of white powders… my aunt used to tell this story about the days when she smoked cigarettes. She used to make occasional driving trips across the US-Canada border. Back in those days, border control was pretty lax, but she was randomly stopped once and her car was searched. The agent pulled open her car ashtray to find it full of white powder. She had put baking soda in to control the cigarette odor, but it was tense few minutes while he figured that out…

    Anyway, aren’t those Tide pods full of *liquid* detergent? So you can’t take that many with you, and they have to fit in a 1 quart bag, etc etc etc. I’m more worried about the quantity I would need for an extended trip, than that they would burst. Just wrap them in a few ziploc bags.

  17. Being an engineer I’m pretty detailed oriented and usually it saves me but when it comes to trips, other than the flights and hotels, I don’t plan my days. You never know how you’ll feel so I avoid all bus tours, and a detailed itinerary. I’ll set some goals like visiting this castle or go somewhere else but won’t plan to be at place x at 0800 and then the next place at 1000, etc.

    Long term travel can be really difficult with “simple” things. An ex-coworker retired and he and his wife are living on a sailing boat so they don’t have a permanent address (sold the house). They had to jump through a lot of hoops to figure out where to forward mail to, etc.

    Post 9/11 even getting a PO Box requires a permanent address.

    I’m surprised someone hasn’t come up with an easy and affordable way to do laundry on the road considering we can get Amazon deliveries in a day or two, Uber/Lyft, gmaps, etc. You’d think you could set up an app and a laundry service and pick things up in the morning and get it delivered that night or the next day for a reasonable fee (and not the incredibly outrageous hotel fee).

  18. Excellent article! I’ve just forwarded this to my son who’s embarking on an open-ended trip following his upcoming college graduation.

  19. You lucky, lucky people who can pull together three months of leisure travel. I haven’t been able to get more than three weeks off together in the last 15 years. My advice, when you visit a place, even briefly, like this trip of James, do it keeping in mind that you may never get a second chance – careers have a way of taking over in middle age – take it from me. I spent three months in the Greek Islands after college and my big regret is that I didn’t get to the mainland to see the important stuff. Planning is important but free form is good for the soul. Nice job, James!

  20. Spot on about the laundry. I remember a few instances where I spent more time than I’d care to admit trying to find detergent. Now I make sure that my Airbnbs have those stocked.

  21. And I forgot to mention about the laundry problem – there are usually owner/operator type folks in European laundromats that will take care of a load of laundry complete from start to folding for under $10. I have people I’ve used for years in selected cities where I travel frequently on business.

  22. Nice post. I like the bottom picture, with the lovely beach and the rocks. Where is that?

  23. @ Christian – I raided the OMAAT image library for some of these images! That is Los Cabos, Mexico.

  24. 2 years ago, my wife and I both took a leave from our jobs and left LA w/ our 2.5 year old daughter on a one way ticket to Bangkok to travel until we were ready to come back home. A lot of what you wrote is very good advice that we practiced on our trip. We had the first 7 nights in Thailand booked and the rest of the trip was booked as we went along. It was stressful at times as I was constantly researching online on where to go next or where to stay or how to best get there, but it was the best experience of our lives.

  25. In the U.S. there are a few companies that will scan and email your mail for you. They all seem to have mixed reviews however. I went with a family member — also mixed reviews.

  26. Great post, James!

    One thing I would add is to be sensitive when planning relaxing time after hectic city exploring time. I’ve booked myself a resort stay after a week and a half exploring big cities and I found myself shocked by the sudden change of pace and couldn’t enjoy the relaxing time because I wanted to be back in the action.

  27. Take a bit of laundry into the shower with you every couple of days, shampoo makes great laundry soap. It will only add 2 – 3 minutes to your shower and you’ll have clean stuff to hang up.

  28. Another vital consideration is medications. Even if you’re only talking over the counter and not prescription meds, it is very likely that with extended travel you will end up in a country where Tylenol isn’t sold or something as ubiquitous as Neosporin may not be available without prescription. There is no need to stuff your luggage with medication (probably a bad idea depending on your destination) but packing the essentials so you don’t have to search for a pharmacy every time you need something as simple as a bandage is good sense.

  29. Another great article, James. What a treat to read it.
    Out of curiosity – have you been to Portugal? Noticed you missed it in your 100 day trip across Europe.

    Cheers & keep up the good stuff!

  30. @James – the important question is whether that evening glass whilst writing is goon, or whether you are raiding the local Tesco for 5 quid plonk 🙂

  31. @ Pedro – I wasn’t trying to visit every European country on that trip! I’ve been to Porto before which was beautiful – hoping to get to Lisbon this summer.

  32. @ Rezzadogs – even though its hard to find in London – an Australian Pinot Noir ; )

  33. $5 to launder a shirt? You must be staying budget places ( these days it’s more likely $10, 15, 20). So I use ‘wash and fold’ service ( and travel with fabrics that don’t require ironing and look presentable without it). Some even collect and return.
    Decent shoes. I don’t understand people who pay a fortune for travel but try to skimp on the basics. A pair of good shoes might cost $3000-500 but are wothrth the investment in comfort and health, IMO.

  34. @ Paolo – if I was being charged $20 to launder a shirt I would just go out and buy a new one.

  35. I spent 3 weeks travelling in 6 West African countries with only a carry-on sized bag. Would have a pain with anything more.

  36. I have just started a 100 day international vacation, I left on the 1st May from the Gold Coast and flew down to Sydney on Qantas and then to Bangkok on Emirates in business class on points and after a week in Bangkok it is on to Dubai for a night then Paris for 5 days where I pick up a rental car for 75 days to travel around France, Spain, Italy and Switzerland before returning home on the 8th August. I read and chuckled when you mention the laundry situation and also find this part of a long vacation frustrating. All the different machines and instructions often in a foreign language and even buying laundry detergent can be a challenge, is it ok for a top loader and a front loader. Though I didn’t plan it i have been lucky enough to select a lot of apartment type properties particularly in France that have laundries in the buildings. Also I find that some items left on the parcel shelf behind the back seat of a car in the European summer dry very quickly if there is no alternative.

    Unfortunately I don’t travel light and on departure I had two checked bags though in total they only weighed 22 kilograms a carry on and a small backpack and in the past this has been a small problem in particularly getting on and off ferries but that is a small price to pay in my opinion and something I choose. I usually have a car so the don’t have the constant on and off trains.

    It is a small price to pay to enjoy 3 months hopefully enjoying a beautiful European summer.

  37. I never plan for my trip (except selecting the destination) and that trip become one of the best trip of mine.. but yes, few things that you have mentioned would always be taken care of regarding the tour.

  38. I hope you didn’t do all of that by plane and that the map is for illustration purposes only. If you did all of that by plane that is outrageously environmentally destructive given the efficient and convenient rail services available in most of Europe and the shortness of some of those hops. Good article though.

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