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5 Trips You Really Need To Take In Your 20s

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

Qasr Al Sarab Me

Moving on…

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!

1) A budget backpacking trip

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, when 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.

2) A trip with more than 12 hours of transit

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.

3) Spend time in a place with a completely different climate from your own

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!

4) Go someplace where you don’t understand the language at all

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.

5) Do something epic

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!

Whatever adventures you decide to go on, just make sure that it’s what you want to do – it doesn’t matter how old or young you are! Also, here’s a great read over at Why wait to see the world.

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


Sunday 14th of August 2016

Traveling solo is interesting but scary. I hope I can find some courage to that soon. Nice article by the way!

Jaclynn Seah

Tuesday 16th of August 2016

You just need to take that first step, you can do it! :)


Monday 6th of October 2014

Great advice :)


Tuesday 16th of September 2014

I am omid that I live in a desert and desert villages of Iran. If you travel to Iran, I invite you to also visit the village.

Jaclynn Seah

Tuesday 16th of September 2014

Well thank you for the invite Omid, I'll remember that if I ever find myself headed that way in future :)


Monday 15th of September 2014

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 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?

Jaclynn Seah

Monday 15th of September 2014

Thanks Huey! Will check it out :) Have awesome travels!


Thursday 19th of June 2014

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.

Jaclynn Seah

Thursday 19th of June 2014

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 :)

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.