Trips To Take In Your 20s | Trips Every Man Should Take In His 20s

Your 20s. There likely won’t be a decade you look back on as fondly for the freedom, excusable irresponsibility and welcome uncertainty they afforded and fostered.

Emotionally, financially and geographically, your 20s are a decade of rapid personal evolution, of hardships and success, and of confusion and clarity. It is perhaps the decade whose beginning feels furthest from its end, yet manages to go by so fast.

Your 20s are a decade ideally suited for traveling, for no other decade’s travels are as likely to shape you as a person or be as diverse. For example, 21 might have you backpacking through Southeast Asia and partying until 7am, and 29 might have you splurging on a couples’ massage at a beachfront resort in the Caribbean.

So while your path through this decade is yours to forge, here are my five humble suggestions for the five types of trips to take in your 20s.


1. Travel By Yourself

Trips To Take In Your 20s | Trips Every Man Should Take In His 20s

Every man should take at least one solo trip in his 20s. Preferably as early in his twenties as possible.

Traveling alone allows you time to think, to be introspective and to learn about yourself. It allows you to rely on your own brain power to solve problems and to make decisions. After all, while there’s no shame in asking for advice and weighing the opinions of others, a man should also be able to make decisions on his own.

Traveling solo will force you out of your comfort zone, and make you feel like more of a real live adult for overcoming the challenges and emotions you can face while experiencing the world on your own. Trust me, you’ll emerge braver, more confident and more outgoing too.

Suggested Destinations: 

A cross-country road trip, or a road trip to a city you’ve always wanted to visit is a good place to start. Better yet, travel out of the country. To ease into it, try Iceland. The people are friendly and they’ll be plenty of other travelers to befriend. To go all in, try a country like Nepal. The culture shock and challenges are real — but so is the beauty and confidence you’ll derived from successfully traveling in such a foreign place on your own.


2. Travel With Friends (And Travel To Party!)

Trips To Take In Your 20s | Trips Every Man Should Take In His 20s

While schedules and budgets might not always align, when they do, jump on the opportunity to travel with your friends. And if you can’t get a whole group together, one or two buddies will do.

Just remember, traveling with your friends should be all about shared experiences, and by default, building stronger bonds. Traveling with your friends is also the perfect time to take the quintessential “your only young once” party trip, especially if you weren’t able to (or didn’t get your fill) in college.

With your wingmen by your side, forget being shy and try and meet as many new people as possible, and use your buddies’ encouragement to try foods and travel activities you otherwise might not try.

Just remember, this is a team trip — chill, go with the flow and have a good time. And even if disagreements do arise on the road, chances are you’ll all get over it in about 5 minutes.

Suggested Destinations: 

For classic party trips, consider Southeast Asia (plan your Asia vacation here) or Greece (island hopping, beach bars and riding ATVs = win win win). Closer to home, try Belize for its surfing and jungle adventures, or rent a boat and spend a weekend at America’s Lake Havasu, Lake of the Ozarks or one of these other party lakes. In the winter, you can’t go wrong with a ski trip to a mountain like Breckenridge.


3. Travel With Your Significant Other

Trips To Take In Your 20s | Trips Every Man Should Take In His 20s

Chances are, your 20s will be your most formative dating years.

But before you get down on one knee, travel with your girlfriend or boyfriend. And not just a weekend trip. Go somewhere for at least a week — and the further away the better.

Why? Because traveling with someone is the fastest way to figure out what they’re made of. Are they adventurous or timid? Do they buckle under stress or can they go with the flow? Are they fun-loving or a Debbie downer? Can the two of you talk for hours on a plane but also exist in comfortable silence? Does their presence make experiencing wherever you are ten times better? Bottom line: if you don’t match up on the road, you probably won’t match up in the long term at home.

And if you’re years away from thinking about marriage, you should still travel with your significant other(s) as much as possible. On the pro side, travel can seriously spice you a relationship (because couples who travel together have better sex lives). And on the flip side, traveling together might just be the fastest way to figure out if you should keep dating or move on to someone new.

Suggested Destinations: 

 The newer the relationship, the easier you should keep your travels. Try a weekend trip to The Hamptons, Palm Springs or Nashville. Moving forward, try a California Road Trip to see how well you do in a car together for hours. From there, go for bigger and more travel-heavy trips, like a multi-city trip in Spain, Australia or Peru.


4. Travel With Your Brother

Trips To Take In Your 20s | Trips Every Man Should Take In His 20s

There’s no other relationship quite like the relationship shared between brothers.

A brother is your first and most important best friend, and your relationship should be one you work to grow as strong as possible as early in your life as possible. The perfect way to continue building that bond and acquiring even more lifelong memories: traveling together.

But you need to act now, while you’re both free of responsibilities likely to arise in your 30s — like having a wife and kids.

While later life’s responsibilities won’t prevent you from traveling together entirely — it’ll certainly change where and how you travel together (say goodbye to partying with your bro in London, Bangkok or Montreal like you used to and hello to wholesome family vacations).

Don’t have a brother? There are just as many reasons to travel one on one with your sister, your dad or your mom.

Suggested Destinations: 

Try Nicaragua (staying and surfing at Maderas Village is a good idea), hiking in New Zealand, beach-hopping in Vietnam or exploring Vancouver Island. 


5. Travel To Learn

Trips To Take In Your 20s | Trips Every Man Should Take In His 20s

While you’ll always learn something about the destination you’re in, even if it’s strictly a party trip, think about how much you’d learn if you took a trip for the primary purpose of learning.

This doesn’t mean you can’t party, it just means you’re traveling for more than just the crazy stories. This also doesn’t mean you need to spend you entire trip in museums (although you should visit museums and spend more than an hour). You can travel to learn about beer, to learn a language, to learn about where your great grandparents grew up or to learn about a historical event or city that fascinates you.

Whatever it is, you’re traveling because you’re interested in something — and a man who pursues his interests and pursues knowledge is the kind of man you want to be and the kind of man people want to know.

Suggested Destinations:

This entirely depends on what you’re interested in and what you want to learn. The world is your oyster.


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Trevor Morrow
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Trevor Morrow

Trevor is a traveler, writer and video maker on a mission to help you craft the best travel experiences possible. From adventurous trips with friends, to romantic trips with someone special, to splurge-worthy trips of a lifetime, he's got you covered.
Trevor Morrow
Follow TMT!
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