5 Trips You Really Need To Take In Your 20s

Jac in Liwa Desert UAE

A little extra reflection as I officially leave behind my 20s and embark on the great journey into the next decade of my life. I started The Occasional Traveller in my mid-20s, but even before I started blogging I had already accumulated some travel experience with my family since I was little. My 20s travels were significant because there were many firsts – first solo experience, first trip without the family, first actual solo trip

Each of these trips has been instrumental in shaping me in to the person that I am today, so for my 20-something year old readers out there, the young ‘uns reading this, here’s my sage advice for you on 5 types of trips you should take in your 20s, when you’re old enough to be independent and legal for most things, yet young enough to really have a ball of a time (and recover quickly from it!).

Remember though, that age is no limit to travel, and an older or younger person could still appreciate any of these trips I’m describing below. Also, it doesn’t mean you have to take 5 separate trips – you could possibly achieve all 5 milestones in a single trip if you are creative!



Trips in your 20s - Backpacking Sheep
Bring the important stuff but leave the sheep at home, no matter how little space it might take up! Pic by Mohammed Jawed via Flickr CC

Set yourself a modest budget for your travels and stick to it – Squeeze your belongings in a backpack and sleep in a shared dormitory with ten other people so you can afford an extra few days of travelling; Scout out freebies and bargain on everything you can to stay within your daily budget; survive on street food and the cheapest booze you can find so you can afford to fly home. Technically, you can do this at any point in your life, but you’ll probably weather it best in your 20s, where you’re young and foolhardy enough to gloss over too-thin mattresses, bumpy tuk-tuk rides and piss-tasting wine.

Do this to fully appreciate the value of getting what you pay for when you can afford it – you will only truly value the simple pleasures like good service, cleanliness and a full stomach when you’ve experienced what it’s like to do without. You’ll also learn much more about yourself as you figure out quite quickly what are necessities to your way of life, and what you can do without.

>> Read about my Taiwan Trip back in 2007, as a recent graduate on a budget for my first backpacking trip.




Trips in your 20s - Long Train Ride
I’m pretty sure that’s how we all look by the time hour infinity rolls around… photo by Jonathan Kos-Read via Flickr CC

It’s all about the journey and not your destination. Whether it’s an ultra-long bus and train ride or a cross-country road trip, hop into your desired mode of transport and watch your day go by and the miles pile up as you trundle along to your next destination. You’re young and have all the time in the world, right? Also when you do finally reach your destination, you can toss your bags aside and start exploring the new place immediately, a thing your body will find it harder to do as you get older.

Long journeys provide you lots of free time to ponder life and its mysteries – it can be hard to catch up on your reading or writing on a bumpy ride, but you’ll never need anything but quiet time to think. You will learn to appreciate the efficiency of modern day travel, but also gain patience and appreciation of the slow ride. Or perhaps just gain the ability to sleep anywhere at anytime, moving vehicle or not, and that is a great skill to have as a traveller!

>>Read about the time I took a 16-hour train ride from Danang to Hanoi.



Trips in your 20s - sand rainbow
This definitely doesn’t look like home (but I could live with that!) Chasing the Gold by Kris Williams via Flickr CC

Nothing says ‘you’re not in Kansas anymore, Dorothy’ like a climate that you’ve never encountered in your life. Beach bunnies, look for snowy mountains and chilly winds for a change while Eskimo types can try heading for the deserts and rainforests. The weather is one of those fundamental things that you don’t quite notice when everything is going well, but can wreak total havoc on your travel plans if it wanted to – cancelled flights, closed attractions, or just general discomfort – not everyone adapts well to a change in weather, but you’re definitely likely to handle it better while you’re younger and stronger.

You’ll either love it or hate it, but either way you’ll surely appreciate the reminder that Mother Nature is all powerful, and that the world is a much larger and more diverse place than your comfortable little hometown, especially if you live in a stable place like Singapore, sheltered from natural disasters

>> This tropical-city girl is not much of a snow bunny, but I survived Munich’s wintery Christmas just fine!



Trips in your 20s - Language
Korea was the destination of my first solo trip, and man the language is really just a bunch of shapes and lines to me (this is coming from soneone whose mother tongue is Chinese!) Photo by Alfonso via Flickr CC

Visit a place where you can’t read the signs nor speak the language – where even the simplest things like asking for directions becomes an adventure in itself. You may end up lost for hours, ordering something you didn’t intend or just end up not speaking for days because there is no need to.

It will teach you to be adaptable and creative as you figure out how to make yourself understood. It will keep you humble as you learn to put your trust in strangers and how to trust your gut when nothing else makes sense. You will also learn that some things are universal and very much the same throughout the world, no matter how foreign it may seem or what language we speak, and it’ll keep your mind open as you move on in life.

>> Read about my first solo trip to Seoul, where I made it through a week even without understanding the language, and a particularly frustrating attempt at ordering lunch.



Trips in your 20s - Leap
. You don’t literally have to leap off a cliff to be epic! Photo by Shiv Shankar Menon via Flickr CC

Imagine that one cool story you want to leave behind for your hypothetical grandchildren to remember you by – whether it’s hiking the Amazon or going to your first music festival, going bungee jumping or just travelling out of your country for the first time, there is no better time for being awesome than in your 20s; you’re old enough to be independent, generally less burdened and legal in most aspects, yet young and foolhardy enough to take up any challenge that comes your way.

Push your limits and find out what they are, because you’ll never know until you try! Besides you need some great memories to enter the new decade with!

>> I’ve rolled down sand dunes, I’ve eaten raw Chicken, I’ve been touched by a manta ray… It’s not the most impressive list, there’s till a lot more room for epicness though, but I am giving it a shot!


If you’re a young working adult in your 20s trying to balance life and travel, stay tuned to the Travelling Occasionally section, or here’s a great read over at Twenty-Something Travel.

What are your suggestions for trips you should take in your 20s? Share them here!

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26 comments to 5 Trips You Really Need To Take In Your 20s

  1. Love your blog. From experience, another thing you should try is getting lost. I’ve gotten lost in too many places to count but like everything you’ve listed, it makes for awesome experiences. (:

    Also, I think you should check out this website I’m working at http://gobeyond.sg
    We feature stories of Singaporeans who have been to countries off the beaten track – think Latin America, Africa, Middle East, South and Central Asia. Inspiration for your long trip?

  2. Jac I love these suggestions. I’m only a few weeks away from 30 and I’ve done most of these trips, except #2 (did 8 hours in transit) and #4 (I mean I was in Europe, but everywhere I went people still could speak English, so I don’t know if that really counts). I would also add these trips for your 20’s.

    – A solo trip. Traveling alone can be an amazing life changing experience. Even if it’s just a weekend away at a nearby city.
    – A road trip with friends. I love road trips, and there’s nothing better than hitting the road with friends, stopping at quirky attractions along the way, singing along to the radio on the way, and ending at a fantastic destination.
    – A family trip. Traveling with your family as an adult is a different experience than traveling with your family as a kid. I learned a lot about my family, and myself during a family trip to Mexico for my cousin’s wedding. I also drove my grandparent and great-aunt to Kelowna (2 day trip) and it was a great experience.

    • Thanks Alouise! I have to say the 16 hour train ride was probably more comfortable than the 12-13 hours it takes me to fly to Europe from Singapore, but probably because I can lie down flat and walk around with a good view šŸ™‚

      A solo trip I think is definitely something one should embark on at some point in one’s life. Whether 20s or whenever, but it’s true that you’re properly ‘legal’ for most things in your 20s so that’s a good time to do it!

      Same goes for the friends bit, I’ve always travelled with my family most of my younger days, so travelling with friends was pretty liberating (and quite interesting) for me!

      And yeah it’s different with family – It’s great because we have a whole history of memories to recall as well – still enjoyable though, but quite different feeling.

  3. [email protected] says:

    All my time during my 20’s I have been traveling solo around my country (Philippines). Last year I have decided to travel farther places and end up being here in Singapore. It was my first time to experience being in the budget trip as the exchange rate in this country is much higher than my country. At first, I find everything was expensive. Then I just have to learn from that experience. I learned to prepare my own pack lunch and re-cook left unspoiled left over foods to keep up to the minimum daily spending thus I can use the savings on buying things I want while traveling.
    The next experience that I had while on a solo travel is when I went to Europe last March. It was my first time to travel more than 12 hours in the plane. I felt uncomfortable during the flight but later on I just got used to it and maybe I was also very excited to land to my destination country (Spain).
    When I landed at Spain, I felt the experience of different weather condition (12 degree celcius) and being with people speaking a different language. Thank God I was able to understand and speak a bit of Spanish that made me communicate with the people there. It was a very exciting experience.
    The excitement of flying out to a new destination always helps me through the flight too. Coming home is often a different story!

    • great experiences Clariza! Your 20s sound pretty happening šŸ™‚ and yes I love Spain too!

      I think in your 20s, you’re just more hardy and resilient, and not so dependent on comfort and little luxuries, so travelling is just easier that way…

  4. Nice read! I agree that you need to at least take one of all those trips. I would add a few other trips I’ve found to be defining in forming your identity as a traveller. Do at least one multicity/ multi country trip. If anything it teaches you how to organize and plan for different things (including packing!). Also do a trip with your closest friends. You may be surprised to find out you’re not the most compatible to travel together and may appreciate your differences a bit more (or find out you love each other more and more)

    • great advice! I think friends you travel with and stay friends after are your friends for life šŸ˜›
      and yeah multi-city is pretty exciting – I went from hot UAE weather to Munich winter, that was pretty surreal!

  5. Still in my twenties (but only for a couple more years šŸ™ )… and I totally agree! Left my job to travel more and haven’t regretted it yet.
    Just wondering if you have tried couchsurfing! Surfed a couple of times and would totally recommend it as one of the trips we should take in our twenties too.

    • Awesome to hear Hendric! I haven’t tried couchsurfing though I’ve heard fairly good things about it so far, and yeah that might be something you’re more willing to endure as a younger person who doesn’t mind literally sleeping on a couch! Could depend too – though I value privacy more now, I think I’ve gotten friendlier with age and am more sociable now than I was a couple of years back šŸ˜›

    • And it’s great to see that Manfred! It does make me feel better about growing old – some people think your travels have to end as you age, but for others like you and Suzanne, it’s like you’re just getting warmed up! šŸ™‚

  6. Did all of the above Jaclynn and would join you in recommending it. Became a lifelong travel addict and revisited some of the early destinations on a much larger budget but the original perspectives were priceless

    • Thanks Paul! I always wonder about whether I’ll revisit a lot of early destinations because there just seems to be so many other places in the world to visit! But yeah I’d love to see how my perspective shifts with age and experience šŸ™‚

  7. Welcome to your next decade! Travel wants, needs and circumstances definitely change as one proceeds through life’s trajectory. As I’m about to enter a new decade myself (yours X 2), I realize, looking back, that each phase had its highs and lows, but overall, I can say, “no regrets” — partly because I followed the advice you give in this post. (BTW, I love your first photo with the guy on the bike with a sheep on his back. You nailed your advice there too — definitely, leave the sheep at home!) Travel on and write on!

    • Never too late to just give it a shot! For all you know, maybe you might just like budget backpacking šŸ™‚

      And also a must-try for the solo trip! It doesn’t matter even if you decide you don’t like it in the end, just giving it a shot will really make a lot of your travel priorities and style clear!

  8. Great advice! I agree on all of it, especially the one about budget backpacking. I’m in my thirties now, and I feel how “comfort” and “luxury” are gradually becoming more and more important, when I travel:)

    • Thanks Mitzie! Somehow I was a lot more willing and able to just put up with bare necessities back then, but perhaps it comes with having more disposable income and an aging body that being comfortable is pretty important now šŸ˜‰

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