5 Trips Everyone Should Make in Their 20s

Last summer, I was blessed to be able to attend the destination wedding of one of my dearest friends, whom I hadn’t seen in ages. We met while studying abroad, and were practically inseparable for months. To this day, it’s possibly the most “like a sister” relationship I’ve ever had with someone not related to me. Still, life happens, and being separated by several continents took its toll. Then, she invited me and several other study abroad friends to her big day, and we made it happen. It was one of the sweetest, most genuinely fun and heartwarming reunions I’ve ever had.

And a year later, it’s got me thinking. (Thanks, #FacebookMemories.)

I’ve had some pretty awesome adventures in my life, but my twenties have brought some incredible memories. And I’m not alone. Almost anywhere I go, whenever I make new friends who’ve traveled, no matter how old they are, there’s something about The Twenties. It’s the decade of exploration, both geographically and introspectively. And nothing beats when the two go hand in hand.

So in recognition of enjoying my final six months of this decade of escapades, I’ve compiled a list of what seem to be the best trips every twenty-something should experience.

The Crazy Week with Your Ridiculous Friends

Let’s just go ahead and get this out of the way. Traveling with a group of your closest friends is the best. Especially when you have the energy to keep the party going for the entire trip. Pick an exotic location and just go nuts. Dance all night. Drink all day. Pretend you can speak the local language better than you actually can. Be nice to everyone and be up for anything. This is the trip your kids will grow up dreaming about taking because 30 years later, whenever you get a little tipsy and start reminiscing, it’s your go-to reference for the most fun you’ve ever had.

Best experienced when: You have any reason to celebrate anything at any time.

The Self-Discovery Trip


Dogs also make excellent travel companions. (@Theodore Roosevelt National Park)

A few exes ago, when I was freshly single and not-quite-ready-to-mingle, I decided to go off for a weekend alone. To be honest, the “weekend” turned into a really long day and partial night of trying to navigate my way around a mountainous region that even my GPS gave up on. But overall, the escape was a success for what I needed at the time. So when a few years later I needed a major change of pace, I decided to up and move myself, my dog, and all of my things across the country. Alone. I’m not the most patient person, but I was reminded during both of those trips that there’s something almost charming about hitting the road alone to just explore and give yourself the solitude to reconnect with nature and with yourself. Both journeys surfaced moments of fear and doubt, but I wouldn’t trade the experiences for anything. There’s a lot you can learn about yourself when yours is the only voice to listen to.

Best experienced when: You’re questioning everything and wondering how you got here.


Only BFFs pull over to the side of the road to awkwardly pose in front of border signs.

The BFF Reunion Road Trip 

This is probably a top contestant for the Best Trip Ever award. Just make sure you choose the *right* BFF (so I’ve heard). In my case, I couldn’t have chosen better. Even though we grew up together as cousins, we’ve sometimes lost the communication battle against time and space. Still, whenever we get to see each other, it’s effortless to pick up where we left off. And even though it was just a couple days of driving down the Pacific Coast, it was one of the best adventures I’ve had. I was left feeling like nobody knows me better, we could tackle anything, and even if the universe decided to test our bond, we’d just come out stronger for it. I started with a best friend and I ended with a sister.

Best experienced when: You need to get away but don’t want to do it alone.

The Parental Escape

Don’t freak out: You WILL get your adventure on during this trip. And you will never regret it. I’m not talking your average “family trip.” In fact, I think it’s safe to say that your kids will probably be in college before you’re ready to tell them the truth of what went down during this trip; of how their grandparents behaved like utterly ridiculous and phenomenal human beings. Because here’s the thing about being in your twenties: Your parents are starting to see you as an adult. Sure, you know you’ve been an adult for years, but now that you’re out of the house (hopefully), they’re actually starting to see you as one. So when they ask if you’d be interested in going to anywhere but here with them—just you, no siblings—say yes.


Ziplining in the rain? Pura vida!

First of all, even though you’re an adult, let’s face it, you’re broke. This is (at least partially) a paid trip. Take it. Secondly, yes parents are desperate for bonding, but even more than that, they want you to think they’re cool. That they can connect with you. This is your chance to make them prove it. Get your mom to smoke hookah and zipline. Get your dad to ride a camel. Get them to dance in public like they haven’t since before you were born. It’s pure magic. And if it’s only with one parent, well, even better.

Best experienced when: Mom and/or Dad needs a break and they miss you.  

The Summer Family Camping Trip

Growing up in the Pacific Northwest, this one doesn’t seem like a big deal. It might even be a little confusing. I know literally just one person who lives in Seattle but has never been on a family camping trip… but she didn’t grow up here, so I don’t hold it against her. Still, there’s something about joining the Family Outing as a Twenty-something that sets it apart… especially if you grew up in a big family like mine that seems to always have a healthy dose of toddlers and preteens running around the camp sites. As the “older kids” become outnumbered, it becomes less and less cool to join in. There are friends to hang with. Sports to practice. Books to read. So you ditch. The years pass and people stop expecting you and don’t bother to act sad that you’re not there. But then, one summer, all of your friends are busy. All the sports are on hiatus. Nobody is getting married or having a baby or celebrating a birthday. There is literally nothing else to do. So you show up to the camping trip. And it’s completely unsurprising how nothing about it has changed. And it’s completely comforting and endearing and fun. The Aunts all miss you and love that you made it. The Uncles offer you beers. And the cousins want to hear any and every story you’ll tell, and crawl all over you like a jungle gym and show you all their newest tricks and discoveries. And life is wonderful.

Best experienced when: Nostalgia and nature are your best bets.

One comment

  1. […] 5 Trips Everyone Should Make in Their 20s […]

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