How Do You Know You’re Ready for Long-term Travel?

by Brenna Holeman

Koh Lanta 8

In Koh Lanta, Thailand in 2011, at the start of my long-term travel around Asia

I was recently on the beautiful Thai island of Koh Lanta with my friend and temporary travel companion Kate of Adventurous Kate. We’ve both had our fair share of long-term travel; she has been nomadic for the past five years, and I have lived abroad since leaving Canada in 2006 (save a few stints of work in my hometown when funds were low). My longest trips were to Europe (for four months), Southeast Asia and the Subcontinent (for nine months) and Central and South America (for nine months). Each time, despite the planning and the packing and the excitement and the worry, there were moments when I stopped to think if I was indeed ready for long-term travel. It’s a huge decision, after all.

I’ve received a few emails from readers over the years asking the same question: “How do you know you’re ready for long-term travel?” I totally get it. You know you want to travel. You’ve read the packing lists and advice blogs. But how do you know that you are definitely ready to take the plunge to travel for two months, six months, or… indefinitely? Long-term travel may not be for everyone, as it is vastly different than a week holiday to the beach. It requires a bit of planning, a lot of optimism, and a healthy dose of an open mind. And while it can be incredibly rewarding, exciting, humbling, and FUN, it can also be stressful, challenging, and eye-opening (none of which are necessarily bad experiences to go through in life).

So, how do you know if you’re ready for long-term travel?

Brenna in Moscow

Travelling through China, Mongolia, and Russia for two months

You know that you won’t be satisfied until you do it. This is probably the most important point. It’s totally fine to have doubts, and to question yourself before a long adventure (or any adventure), but if you know in your heart that your wanderlust won’t be satiated until you try it, you’re on your way to creating an incredible long-term journey.

Italy 3

Burano, Italy

You’ve planned your finances. I am always very suspect of bloggers and travellers who say things like, “Anyone can travel!” Well no, not everyone can, and I consider it quite an elitist statement to make. The truth is that travelling costs money, and so you need to be in the position where you are able to save at least a little bit of income in the first place. Travelling doesn’t necessarily cost a lot – there are loads of countries where you’ll spend much less as a tourist than what you probably spend in your home country, depending on where you’re from – but it is vital to accurately plan your finances before, during, and after your travels. Things change of course, and you can never know exactly how much you’ll spend, but it is important to have somewhat of a handle on what you’d like to spend daily or monthly. If you plan on working on the road, or becoming a digital nomad, that’s also something to research and consider when managing your budget.

I’ve written extensively about how to save money to travel the world, including a history of how I saved money to travel. I always recommend that people save a bit more than they’re planning to spend (for emergencies and/or special situations and experiences) and that you have a bit of money saved up for after your trip so that you don’t return to absolutely nothing in the bank (if you’re planning to return, that is).

Guatape Colombia

In Guatapé, Colombia during a long-term stint of travel around South America

You’ve tied up any loose ends. I talk about this in the post How to Plan For a Very Long Trip (which you might want to read if you are indeed thinking of long-term travel). If you are planning to leave home for an extended period of time, you need to think about the logistics of leaving your home life behind. Will you need to quit your job? Will you need to pack up your apartment? Do you have a pet that will need taking care of? If you’re travelling with a friend, partner, or family, how are each of you going to contribute to the trip? (By the way, you can read more tips about travelling with your best friend here.) The sooner you take care of these loose ends, or things that may hold you back, the better – it means you’ll have more time for all of the fun stuff, i.e. planning your dream adventure.

Yangon 6

Yangon, Myanmar

You’ve discussed your trip with your family and friends who won’t be joining you. I believe it’s good to talk about your dreams and desires with those you love. If you don’t have anyone in person in your life to discuss these things with, I suggest taking a look at online forums, blogs, and Facebook groups about long-term travel; the internet is full of them, and I’ve always found it to be a very welcoming community.

Convincing your friends and family that you want to travel long-term can sometimes be difficult; I’m well aware that I was extremely lucky that my loved ones all actively encouraged me to travel (um, unless that was their subtle way of trying to get rid of me). I will be writing a blog post about this subject soon, but ultimately, only you will know how to deal with your loved one’s fears or discouragement. I think that providing them with as much information as possible – blogs of other long-term travellers, for example, or your expected itinerary – is definitely a way to help.

Pai Thailand 6

Pai, Thailand

You’ve thought about how you’ll cope with the bad days. Unfortunately – just like life – travelling isn’t all unicorns and magic. While the happiest days of my life have all occurred when I’ve been on the road, I’ve also dealt with loneliness, illness, anger, grief, frustration, heartbreak, and just about every other negative human emotion or feeling while I’ve been travelling. Depending on whether or not you’re travelling solo, you may or may not have your usual support network to rely on if you’re far away from home. This doesn’t have to be a scary thing; it can actually be quite empowering and esteem-building to know that you’re able to handle these things on your own. I honestly believe that if I didn’t travel, I’d still be the girl who occasionally panicked about trying a new restaurant because I might not know where the bathroom is (yes, really). Travelling is the best thing that’s ever happened to me, but – again, just like regular life – I’ve still had to deal with some tough shit while doing it. It’s OK if you feel nervous about dealing with these emotions far away from home, but it’s also important to emotionally prepare yourself that not every single day will be perfect. Make sure to include some down days in your travels; it’s crucial to be able to rest and reflect.

Vientiane Laos 1

Vientiane, Laos

You’ve educated yourself on the countries you want to visit. This goes beyond which visas you’ll need or how to say ‘thank you’ in the local language. I think it’s a great idea to read up on the places you’ll visit for some knowledge of the country’s customs, geography, history, politics, and their approach to tourism (either online or in guidebooks – most guidebooks have a great section at the front with necessary information). This shows a level of respect but it also will mean that your trip will start off a bit smoother. It will also help you to engage with the local people more.

In terms of planning where you want to go, I would suggest not creating too tight of an itinerary; travelling long-term means that you’re able to go with the wind, so to speak. However, I would recommend researching the countries you’d like to visit and figuring out their best seasons, when certain holidays occur, and so on. I personally never plan anything in much detail on a longer trip, because I believe it’s good to be spontaneous once in a while… plus you never know who you might meet, or if you’ll fall in love with a place and want to stay longer (or the opposite), but I do always read up on a country to figure out the ideal time to visit and the best route to take.

Amritsar India 8

Amritsar, India

You’ve vowed to keep an open mind. I always think that, above all else, the best traveller is one with an open mind. If you’re going to travel long-term, you must accept that life will often be drastically different than the life you’ve left at home. As mentioned earlier, that can be very challenging, but it will most likely be exciting and invigorating, too. You will see and do some truly amazing things, things that were only possible because you decided to take the plunge and travel. And if you do it all with an open mind (and, as I always say, an open heart, open eyes, and occasionally, an open wallet, too), you’ll have one of the greatest and likely most life-altering experiences ever. Vow that you’ll be open about new places, new people, new experiences, and that you’ll let your open mind lead you on some wild and beautiful adventures.


Machu Picchu, Peru

At the end of the day, sometimes you never really know if you’re truly ready. But if you believe you are, and you have your finances in order, and circumstances are right, and it’s what you want more than anything… all right then, what are you waiting for? Just book the ticket. You won’t regret it, I promise.

Have you ever travelled long-term? How did you know that you were ready for it?

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Christine November 30, 2015 - 4:59 pm

YES re being financially ready. I hate it when I hear about people going into debt or quitting their job with absolutely no plan. I love travel, but I think that it’s important to do it responsibly and take all of the factors you outlined above into account. Great post!

Brenna Holeman November 30, 2015 - 5:15 pm

Thank you so much, Christine! I’m glad you like the post, and glad you agree that it’s so important to be financially ready, too.

Rachael December 2, 2015 - 6:31 pm

I agree! I’ve just recently come back from travelling to zero money in the bank, and had to rely on my parents a bit before I found a job. AND, travelling is so much more enjoyable when you’re not worrying about if you can afford dinner!

Brenna Holeman December 3, 2015 - 2:11 am

I agree – I’m glad I often waited a couple more months just so I could save as much as possible instead of rushing off without as much money (and then having to either really stretch my budget or come home early). Saving more allowed me to occasionally do things that were more expensive, like scuba diving, paragliding, or language classes. Thanks for your comment, Rachael!

Jenia November 30, 2015 - 9:09 pm

I would add one more — you know you are ready for long term travel, if you want to do it, AND, circumstances align just right. For us, we were both ready to leave our jobs when we made the decision, we had paid off most of our student debt, and we had finished a major house renovation all within months of making the decision to just go.

Brenna Holeman December 1, 2015 - 4:59 am

Yes, that’s a great point, Jenia! I suppose that falls under the “loose ends” category, but you’re totally right.

Elina November 30, 2015 - 9:20 pm

Huh, the first time I travelled anywhere alone was for nine months and before reading this I didn’t consider it long term (I had plans to come back etc) but now I’m like yeah, I guess it was. So maybe that’s how you know 😀

Good points though, especially the finances. I am hoping to make money as I go but I am terrified that I wouldn’t be able to make enough money to get by because that’s happened before. I slightly disagree about planning though, it is important but at the same time if you already know your plans exactly you’re gonna miss all those other places where your new travel friends invite you to tag along to 🙂

Brenna Holeman December 1, 2015 - 5:00 am

I never think you should plan things down to the day… but having a rough idea of where you’re going and when it always nice (in terms of knowing the seasons, knowing when your friends will also be in town, knowing when there’s an event, and so on). I personally never plan trips in much detail but I always have a rough idea! And if those ideas change, well, that’s fine, too. 🙂

Rachel December 1, 2015 - 2:02 am

I think that you’re first point was the kicker for me. I just KNEW if I didn’t travel long-term, I’d never be satisfied and I’d have so many regrets. I’d never get over it and I’d probably never stop browsing travel blogs while I worked at a job I didn’t really care for. I’ve been in South America now for two months and it has been excellent and so rewarding. Yeah, there are some lonely days and some other not so exciting days when I need to rest, but nothing unbearable or crazily different from life at home.

Brenna Holeman December 1, 2015 - 5:01 am

That’s so awesome, Rachel! I’m so glad to hear you’re loving it. Have an amazing time!

Paige December 1, 2015 - 2:39 am

I love this post–long term travel is very much my dream/goal right now, but I know I’m still working on getting my sea legs, so to speak. I’ve read lots of “what are you waiting for” type posts, and while I definitely understand the emotions behind that attitude, I know the “drop everything” method wouldn’t work for me at this point in my life. Also, I laughed out loud at the where’s the bathroom in this restaurant problem! (At a recent dinner out I watched two of my friends almost walk into the kitchen and then wander around the back of the restaurant confused at separate points in the meal–the struggle is real!) : ) Hope you have a lovely time in Bhutan!

Brenna Holeman December 1, 2015 - 5:02 am

Thank you so much, Paige! Yes, I agree that at some point you just need to say, “OK, I’m going,”… but it’s also important to have at least a few things in order. I hope that you get to travel long-term very soon, it sounds like you’re on your way!!

Julie December 2, 2015 - 9:32 am

Amen to everything you’ve said. I have always known I’ve wanted a stint of long-term travel (1+ years) and have literally been saving money for over 10 years for it. I have a friend who went the ‘just go’ route and found herself back at home within a few months because the income from a new website didn’t come fast enough to support a family on the road. C’est la vie!

Brenna Holeman December 2, 2015 - 2:00 pm

Thank you very much, Julie! I’m really glad you like the post. And wow – you are going to have such an amazing trip! 😀

Daniela @ Grumpy Camel December 2, 2015 - 10:45 am

Thank you for writing this. I’m glad I’m finally reading something that’s more honest than the ‘just do it’ and ‘anyone can travel the world’ type of articles out there.

Planning finances can seem daunting and disheartening (which is probably one of the reasons many give up on a long-term trip) but I think it’s the first thing that indicates whether it’s the right time to do this. Plus you don’t want to spend the rest of your trip worrying about running out of money.

Brenna Holeman December 2, 2015 - 2:01 pm

Thank you so much, Daniela, I’m really happy you like the post! I totally agree with what you’ve said about finances. A lot of blogs just say, “anyone can travel” without talking about all of the planning and logistics that are behind it… that can be a bit misleading, I think!

Michelle Schroeder December 13, 2015 - 12:07 am

Love this! We are currently traveling long-term and we’re not sure when we will be done. It took lots of planning for us to get to this point!

Brenna Holeman December 13, 2015 - 11:28 am

Thanks a lot, Michelle! Keep having an amazing adventure…

Zalie December 14, 2015 - 12:15 am

These are some great tips and I really hope they encourage people to do some travel planning in the near future!!

Brenna Holeman December 14, 2015 - 10:33 am

Thank you, Zalie!

Kylie December 17, 2015 - 1:02 am

When are you coming to visit the beautiful Australia?

Brenna Holeman December 17, 2015 - 12:36 pm

I have been to Australia in the past… but I’d love to visit again!

The Danger of Someone Else's Dream - This Battered Suitcase December 17, 2015 - 10:31 pm

[…] tons of articles on how to save money to travel the world, what to keep in mind if you’re planning to travel long-term, and so on, it doesn’t mean I believe that every single person will want to follow […]

Helen Manton December 22, 2015 - 12:51 pm

I thought i was ready for long term travel: i am currently doing a 6 month stint around some of SE Asia and Indian Sub-continent. After 10 days, i had a massive slump and considered heading home as ‘i just can’t do this’. A month on from my departure, i am in Vietnam and still continuing the next adventures!

Brenna Holeman December 23, 2015 - 10:06 pm

Happy travels, Helen! I hope the rest of your adventure is absolutely wonderful.

James Kolber December 27, 2015 - 1:31 am

Ready to move, everything is pretty mudane, need to regain eye of the child.
Been gone 5 years now, 11 countries . Still tickin

Sarah September 29, 2016 - 4:29 pm

Love your writing. My husband & I have been on the road for 10 months now with no end in sight & never been happier. Like you say, there are bad days & being away from loved ones is tough but we reached the point we where we just had to just to do it or we would have regretted it forever. Sx

Stephanie April 21, 2017 - 4:48 pm

I’ve had last minute doubts before every solo trip I’ve taken! I think that’s normal- and it’s important to distinguish between nerves and crippling fear.

Brenna Holeman April 21, 2017 - 5:53 pm

Agreed, Stephanie! 🙂


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