This blog post was updated on January 2, 2018.

There’s a sweet spot for traveling that happens when you’re in your twenties. As a teenager, it’s likely that you lack the funds to properly travel… Not to mention that your parents probably wouldn’t let you go skipping around foreign countries by yourself. When you hit 30, avalanches of responsibilities make it increasingly hard to get away. It’s important to take advantage of those ten years—they’ll give you fresh eyes, cultural fireworks, and a deeper understanding of the world you live in. But traveling as a young twenty-something is very different than traveling at 29. Here’s our take on traveling through the years, the best places you should go for every year, and all the ups, downs, and side to sides that come with that age.

When You’re 20, Party in Portugal

Traveling when you’re 20 is exciting and scary. If you’re alone, it’s likely that this is the first time you’re trying to navigate the complicated waters of booking hostels, feeding yourself, doing meaningful activities, and trying not to get too drunk. The Portuguese are incredibly warm, friendly and accommodating.  So when you stumble into your first hostel, clueless and lost,  you’ll be greeted with smiles, directions, and endless amounts of help. Portugal is home to fine food, port wine, and rich music. In Lisbon, there are parties that last ’till morning and mojitos are served in buckets. Cities are filled with Moorish and Medieval ruins and even if you have a hard time planning your days, you’re sure to stumble into something significant. Walls covered in graffiti and little kids playing soccer in narrow and hilly alleyways will feel magical. The smell of fish frying behind unseen corners and the booming sound of fado from small clubs will make you question why it took you so long to leave in the first place (let’s be real, it was probably your parents).

When You’re 21, Sightsee in Singapore

While traveling through Europe at the age of 20 is exciting because the drinking age is low enough that many Americans can experience bars and clubs for the first time, once you’ve turned 21, you’ve gotten the partying out of your system (hopefully!). That means that traveling for culture becomes a priority. The best place for that hotpot of ethnicities is Singapore. The population is a mix of foreign-born diplomats, Chinese, Korean, and Indian immigrants (and more!). Despite its relative age—it’s only been self-governing since 1959, Singapore has become an economically dominant country, earning the title Asian Tiger (the three other Asian Tigers are Taiwan, South Korea, and Hong Kong). Singapore is also a modern crossroad for major religions. Here you’ll find people practicing Islam, Buddhism, Hinduism, and Christianity. The city is also a great start for those scared of exploring an Asian country where the language and food can feel extremely foreign. English is the primary language and because of all the foreigners, many kinds of food can be found. There’s no better place to explore different cultures than in Singapore!

When You’re 22, Unplug in Greece

It’s common for travelers to struggle with deciding exactly which island they should visit when traveling to Greece. For 22-year old young travelers, we recommend you head to the island of Santorini (especially if you’re obsessed with taking photos). It’s known to be one of the most romantic destinations in the world but it’s also a tourist hot spot for amazing culture, incredible views, great history, and of course their unique beaches. Strolling around this island is surely a must as the traditional architecture and landscapes are what the island is well-known for. The white colored houses, churches with blue domes, picture-perfect streets and the landscapes is what you’ll appreciate most about Santorini. Looking to soak up the sun? Then we recommend going to the Red Beach where you’ll be surrounded by volcanic lava red rocks and red sand with crystal clear water. If you have the time, it’s best to take a 7-10 day trip to Greece so you can island hop and see more of the country. The island of Mykonos (popular for its nightlife and beaches) is only a short ferry ride away so it may be a good idea to take a lengthier trip to capture more of what this magnificent country has to offer!

When You’re 23, Explore Japan Confidently

Image via Flickr – CC BY-SA 2.0 – Pedro Szekely

A lot of the Western World shares very similar cultures and values, and sometimes, it can be scary to step outside that comfortable niche. So, it’s wise to take the dive into a very different place after you’ve matured a bit. And by the time you’ve turned 23, you’ll have had the chance to take your first steps into the real world and are ready for the challenge. With that confidence, you should visit a place like Kyoto where the language is foreign, the food is mysterious, and the letters are written in a script that you can’t even read. Learning to navigate and enjoy such a complex landscape is something that should be executed as early as possible because it will build a deep-set confidence that you can apply to the rest of your life. The sight of Japanese castles and cherry blossoms, as well as evenings spent in pod hotels might seem alien at first, but with a bit of courage and a pinch of practice, the strangeness of it all will quickly disappear. Best of all, nothing else will ever feel like a challenge again.

When You’re 24, Go Dancing in Brazil

Image via Flickr – CC BY 2.0 – tetedelart1855

Brazil is complex. The city has recently seen a revival in its economy, it’s been the center of a lot of media attention, and it is the only Portuguese-speaking nation on this side of the Atlantic. When you’re 24, it feels like it’s you against the world. Finding a balance between work, friends, and family becomes more complicated. You don’t know what you want with your future. Maybe some people you know are even starting to get married. The sensual, fun, and punk attitudes of those living in Brazil are inspiring. While you’re here you don’t have to sweat the future, because Brazilians savor the present. Every party, every festival, and every conversation that is presently happening is the most important thing in the world. Going to Brazil at 24 lets you forget about the future and focus on the now. Here, stretches of sand and waves swallow your thoughts and you’re able to understand what is and isn’t important to you.

When You’re 25, Enjoy the Finer Things in France

Image via Flickr – CC BY 2.0 – Pug Girl

Like a fine wine, it takes a little while to ripen enough to enjoy France. Halfway to thirty, you’re young enough to get flushed in the cheeks as your lover, fiancée, husband, or wife drags you between charming Parisian side-alleys, but experienced enough to appreciate the dry sting of an aged and oaky Bordeaux. In Paris, you must spend time to appreciate things. It is not something that can be rushed through youthful bliss, but rather, each bite savored, each kiss lingered upon, and each museum strolled through. But at night, with street lights twinkling on The Seine the city unfolds for those with fire in their hearts. France is best explored in two because cheese tastes better when it’s fed to you and the Eiffel Tower seems lovelier with someone standing next to you. At 25, you should spend time learning how to love someone else, now that you’ve nurtured yourself. Love them as you would want to be loved. And in Paris, with its endless bakeries, cafes, and gardens, you will take the moments necessary to explore the city of love with someone you love.

When You’re 26, Rediscover Yourself in Argentina

Image via Flickr – CC BY-SA 2.0 – Hernán Piñera

As the tides change, and for the first time ever you’re closer to 30 than 20, taking the time to nurture different parts of your life, be it a focus on family, work, or hobbies becomes important. It’s easy to get swept away in professional success, and have the drive and energy to push the limits of work while forgetting to call your mom or get drinks with your friends. Argentina, with its glaciers, rocky terrains, jungles, and beaches is the embodiment of diversity. After all, the best places and the best people are the ones that are diverse—in thought and interests. At 26, you should go to Buenos Aires and spend time embracing new hobbies and discovering new loves. Take a risk and go solo hiking or hit a dance club and perfect your salsa skills. After working through college and your early twenties, it’s time to take a step away from the grind and let yourself breathe. Wake up early and drink the best coffee of your life—not because you need the caffeine to get you through your day, but because the bitter taste of freshly ground Arabica is like nothing else in the world. Eat dulce cakes and wipe the sticky syrup off on your pants. Take a walk under the stars, and let all the deadlines, stress, and tension that has built up over your early 20s go, even if it’s just for a couple of weeks.

When You’re 27, Be Stress-Free in South Africa

Image via Flickr – CC BY 2.0 – David Stanley

There’s a certain amount of excitement and richness associated with South Africa. Its recent conflicted past contrasted with beautiful bleached cliffs and turquoise coasts, a visit to South Africa reminds you that not everything that glitters is gold. Despite South Africa’s recent history, it has turned itself around into a modern, exciting, and lovely place. It’s come a long way in a short amount of time. At 27, it may seem like your future is set in stone and that you’re on defined paths for your personal and professional lives. But a walk along the coast in Cape Town or a drive through Johannesburg will remind you that things can change, and if you’re not happy in a relationship or something else in your life, you can make that change. With homes that are open and minimalist and the infectious mentality that less is more, South Africa can de-stress and unclutter the minds of the busy, driven, and lost 27-year-old. If you’re trying to figure out your future and change your past, South Africa is the best place to go!

When You’re 28, Adventure in Iceland

Image via Flickr – CC BY 2.0 – Kamil Porembiński

As 30 looms in the not-so-distant future, and mortgages and babies become part of daily discussions, the need for a vacation that feels like another world feels necessary. Whether you’re dealing with diapers already or just the idea of them, it might feel like the world is a monotonous routine that is sucking your soul away: wake up, work, sleep, repeat. But there is magic, and it can be found in the sparkling green Northern Lights or in the depths of bubbling sea green hot springs or at the top of rolling green hills. Iceland’s landscape feels alien and that ethereal beauty is so different than any daily routine that it can feel like jumping in a bath filled with ice water. With a population of around 300,000, you can go miles without seeing anyone, and the barks of bosses and the cries of children become distant whispers. Iceland at 28 is perfect. You’ll find places to relax, places to discover, and places to meet people. The change from bachelor to dad can feel strange, but Iceland can help make that transition feel natural.

When You’re 29, Discover Something New in America

Image via Flickr CC Alan Eng

After exploring the world and understanding other people’s cultures, habits, and foods, it’s finally time to understand your own world. If you’re from America, exploring the USA is easier than most of the other listed destinations. For one, at 29, you probably have a myriad of responsibilities tying you down, or even a beloved pet that you can’t stand leaving behind. But the best part about exploring your own country is the fact that you can pile everything you need into a car, head South, East, North, or West and just drive to a destination. In New York? Head to California. In Texas? Let’s head to New York. Pick the spots along the way that interest you the most. This could be a visit to Mt. Rushmore, a night at the Grand Canyon, or a cabin in the Rockies. America has all kinds of sights to see, ranging from spanning plains to urban sprawls—a trip across it is an exploration of one of the world’s most culturally diverse nations. The beauty of a cross-country road trip is that you can make it themed, be it a culinary discovery (BBQ and tacos anyone?) or a long-stretching Museum Mile (American Gothic and more). The ins and outs of middle America have a lot to offer that at 29 are easily accessible and important to know. You never know, it might end up being useful being able to find Idaho on a map.


Have you made some amazing trips throughout your twenties? Let us know what your favorite place was in the comments below!

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Lover of cheese. Trash panda enthusiast. Avid nap-taker and fridge-hunter. Occasionally writes and sometimes travels. Responds to "Chloe" and "Generous Overlord."