The Iconic Travel Experiences You Should Have In Your 20s


Taking time to travel in your 20s is always a good idea. The decade is a sweet spot in life — when endless doors hiding fresh experiences suddenly open up to you. Independence is at a high. The whole world is waiting. It’s a beginning. The memories, successes, and failures you collect along the way will be with you for the rest of your days.

But where, oh where, to start the journey? We’ve compiled a list of some of the bucket list-worthy, iconic life moments we should all aim for in our wanderlusting 20s. These are the trips and journeys that can come to define us going forward. These aren’t specific places or destinations. They’re experiences.

While we don’t put too much credit into the old axiom of using travel to “find” yourself, we do put a lot of merit in using travel to winnow away your biases and fears, pushing you to become a fuller, more open version of you. Let’s dive in.


The backpacker trails in SE Asia, the Surfer Trail down the Central American Coast, the Banana Pancake Trail through Thailand, the Hippy Trail from Pakistan, the Grand Tour through Europe, the Gringo Trail tracing the Carribean…. there are a lot of well-trod trails that’ll help you launch your first adventure. Theoretically, you could start the Grand Tour of Europe in Lisbon and end up in Istanbul, then take the hippy trail across the Middle East and Central Asia to Delhi then jump on the Banana Pancake trail until you end up in Bali. You will not be the first to do it and you certainly will not be the last.

The point is that traipsing across well-worn paths means you’re going to see an incredible amount of the world. Seeing the entirely of the Eurasian continent from the brisk Atlantic all the way to the warm waters of the Pacific is a great place to start a life of travel. You’re also going to find plenty of worldview-sharing, experience craving vagabonds like yourself.


Just to the left or right of those well-trod trails is the whole rest of the world. It’s about going to Bhutan instead of Vietnam with half your high school class. It’s visiting Serbia’s cool winter markets instead of the more famous Christkindlmarkts of Austria. It’s finding the pockets and out-of-the-way spots that will lead to something unique. Real adventure awaits on the fringes of the mainstream.

Look, the trails are great, but come at a cost. Boracay in the Philippines is closing because we’re literally killing it through tourism. Point being: Once you’ve got a few miles under you, be sure to strike out on your own. See the Stans of Central Asia, trek across Siberia, ride a bike through Canada’s Arctic. Find a new place that isn’t already tagged in 20,000,000 Instagram posts and go there.


Travel is never defined by distance. It’s defined by the connections you make and the ways those connections enrich your life.

So, on the flipside of all this globetrotting is taking the time to explore what’s around you. Taking short trips to the national parks, state parks, and points of interest in your own backyard might be the most rewarding travel there is. Eating in your area’s best restaurants, getting to know your nearby brewers, bartenders, and farmers, and seeing the beauty in the world that’s right outside your door is an essential part of a well-rounded life.


You know what else is awesome? Spending some time on a deserted or inhabited island. Maybe take a friend or a loved one, or just rock up on your own. Live by your wits. Eat what you catch. Enjoy the solitude. Take pictures. Write something. Run through the jungle naked. Connect to nature and allow it to nourish you.

Do it safely and smartly. But do it.


Sailing across an ocean gives you the greatest sense of just how gargantuan this planet really is. Another huge benefit is how enlightening traveling around and across oceans can be — because, spoiler alert, you will be tested.

You’re able to see wholly unique cultures from, quite literally, around the world. And then you start to see how connected we truly are. You see the chilis from the Americas in China. You see the spices from Sulawesi in Chile. You see the art of the Siberians in Vancouver. Traveling by sea and exploring the diversity of cultures around an ocean gives you the greatest insight into how truly singular we really are as humans while highlighting the flourishes of our individuality that make our respective cultures all so unique.


Criss-crossing a whole continent is another great way to see the massive size of the earth and the endless depth of humanity, nature, and wildlife. Whether it’s taking a train from Lisbon to Moscow and then getting the Trans-Siberian to Vladivostok or taking the Trans-Canadian from Prince Edward to Vancouver or getting in a van and driving from Cairo to Cape Town, continental travel is a must when you’re young.

By exploring a whole continent at once you’ll realize how small we really are … and how you can spend an entire life and never see it all. Important lessons all around.


98 percent of Americans are direct and recent descendants of immigrants. Most of us have grown up with the nuance of the ‘old country’ in our lives — whether that’s ravioli on the Thanksgiving table next to the turkey or a German Oktoberfest in actual October instead of September, you all know what we mean. White, black, and Asian Americans have a home country that’s not America(n).

Go there! See where your family lived. Sit in a pub in Ireland where your grandfather was born and talk to the locals. Climb a mountain in India to a temple that your grandmother looked at every day on her way to school. See the plains of Africa that were once your own. Connecting to our past and feeling the energy of a place we likely spent thousands of years evolving in and adapting to is a crucial element of life. Embrace it and see what you find. You will be surprised by how familiar it can feel.

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Cold winter’s day in Berlin.

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This is a very subjective option. For some people, it’s the outdoors (it’s filled with bears and wolves sometimes and they will totally eat you). For others, it’s a place with big waves (that will pound you into the sand). For yet others, it may be political hot spots.

It’s up to you. Think about what scares you. Identify it. Research it. Reach out and talk to people who’ve been there. Then go and master that fear (while always being respectful to those living there). Don’t forget the sunscreen.