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Wow, your twenties. It’s a really weird age, you have left high school, you are suddenly classified as an adult, but you barely have financial literacy and you are expected to know what you want to do with your life. That’s pretty hefty stuff. Don’t worry though, you can take one of all of these 20 trips to take in your twenties.

Some of you may continue your education, some may start work, and some may take the leap of faith that will change the course of your life forever… the *eternal* gap-year. Regardless of what you are doing, or where you want to go your twenties are for experiencing things, learning more about yourself and creating memories. 

This is the ultimate 20 trips to take in your 20s! 


There are so many benefits of travelling alone. You have to be entirely yourself, learn to socialize with new strangers constantly and your confidence will grow. This is your selfish trip. Eat what you want, go where you want, and meet who you want. 

Travel your home country (Roadtrip!) 

I’m a strong believer in knowing where you come from. You may hate your home town (or love it and just need a change of scenery) but if you don’t see beyond the city-limits you really don’t know what else it has to offer. Get to know your home country and see all it has to offer. 

Check out our Insider’s Guide to Banff National Park.

Girls (or boys) trip! 

You love your besties, and they love you. Besides someone throwing up and maybe losing a phone (which could happen in your home town anyway) there are absolutely no downfalls to taking a trip with your tribe. 


We love backpacking, and definitely think you should but all-inclusive is a really relaxing vacation that you should definitely experience.  It makes our list of 20 trips to take in your twenties due to the ease of it all. 

The "scare your mom" trip 

Go somewhere that will make mom shudder a little bit. I’m not suggesting going into a war-zone or somewhere that is under siege, but go to a country that isn’t so cushy. 

For me, it’s Africa, mom thinks I will be eaten by a lion or something, but it’s calling me and I can’t help but listen. 

Long-term backpacking 

I’m talking 12months + with just you and your backpack (okay and maybe a travel buddy). Go abroad and live in hostels for a bit, you will meet some of the coolest people ever. Your 20 trips to take in your twenties shouldn’t all be fluffy, you should push yourself. 

You can Work for Accommodation to offset costs!  

Island hopping

This could be all in one country like in the Philippines exploring all the islands the country has, or it could be Island hopping through the south pacific and hitting all the island countries up along the way. 

A family trip

It’s so nice to have some bonding time with your family, and your twenties can get hectic fast, so try to make time to get away with your family. 

Yacht or sail trip

If you get sea-sick this may be a miss for you, but spending some time out at sea could be exactly what you need to hit the refresh button, plus the further away from the land you get, the less cell service (AMAZING). 

Your dream trip 

This is the trip you can’t get off your mind, when you talk about places you want to go it’s the first thing that rolls off your tongue. Take that trip. It should be number one on our 20 trips to take in your twenties list, but if you are new to travelling this shouldn’t be your first trip. Get some experience so you can make the most of your dream trip when the time comes.  

The wild-trip 

Whether it’s Las Vegas or Magaluf take that wild, alcohol-driven trip before hangovers start lasting 2-5 days! 

Don’t worry though, you can get drunk on a budget in Australia

The Awakening trip

This one needs to be taken seriously, this is the trip you take to see how other countries are living and really get a rude awakening. Go experience mud-huts and poverty, you will come back from that trip a new person. Once again, 20 trips to take in your twenties shouldn’t all be fluffy, you should push yourself. 

The educational trip 

Go learn to speak Italian in Italy, or how to ski in Canada. You could visit the Auschwitz concentration camp in Poland and learn first-hand what horrors Jewish people faced. It could also be learning about coffee in Colombia. This trip is to open your mind and teach you something you never knew. 

The volunteer trip

This could be building a village, helping a research facility or helping with the aftermath of a natural disaster. This trip is not about you, this trip is about togetherness and working as a single unit to fix the problems our world is facing. 

Camping or Eco-trip 

Now, we strongly recommend you always do your research and make sure you are being conscious of our mesmerizing planet, but this trip should go a step further. 


There is no better way to experience local culture than to stay with locals (try to convince me otherwise, go on). They feed you local cuisine, know all the best spots that aren’t overturned with tourists and are happy to teach you new skills or words in the local tongue. 

Adrenaline trip 

Spend some time chasing adrenaline. Go jump out of a plane, off a cliff or fly through the air. Dive with sharks, go mountain biking or heli-skiing. Experience the ultimate rush of pure-adrenaline coursing through your body. 

Go to a Festival abroad

What is calling your name the most? A full-moon party in Thailand?The Holi-festival in India? Tomorrowland in Belgium? Burning Man in Nevada? Carnival in Rio de Janeiro? Pick one that is screaming your name and just go for it. 

The challenging trip

 What challenges you will be different from what challenges me or Matt, it could be physical like hiking a mountain or living without indoor plumbing but it also could be mentally challenging like facing your fears of spiders and moving to Australia. This trip is meant to show you just how amazing and resilient you are. 

The underwater trip 

We particularly love this one as we are basically fish. Go on a trip exclusively for diving, or snorkelling. The underwater world is something that can only be felt, there are no words that could ever describe just how magical it is to swim along with angelfish or sea-turtles. 

It seems like a lot, but when you look back at your life when you are 85 years old and are no longer fit for travel they will be the memories you cherish. Your twenties are years to grow and build, but that doesn’t exclusively mean build a career and grow your bank account.

We can’t wait to see your adventure! If you have been on any of these trips share your stories in the comments below, or tag us on Instagram @youptourofficial.

If you are planning your trip and want some advice, please Contact Us we are happy to help you get on the road to living your best life.


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