The Ultimate 20 Trips to Take in Your 20s

Updated May 29, 2020.

Since I recently entered my 30s, I’ve been reflecting on the person I’ve become—what I love about myself, what I wish I’d done before now, what I can improve, why I am the way I am, etc. And I realized on a recent trip to Bali that travel is not only my favorite hobby, it has shaped my life!

I took 5 international mission trips with my church youth group in high school—two to Ontario, Canada; three to Ensenada, Mexico—but I started traveling solo in my twenties, and those trips and experiences have shaped my life in ways I love. Here is my list of 20 trips to take in your 20s to challenge yourself to become your best you!

 1. Your First Trip Abroad

If you haven’t been out of the country by the time you reach your 20s, do it! It will make you wiser, more well-rounded, and help you understand yourself and the world you live in. It will change your life in countless ways! I can look back on my trip to Japan when I was just 20 and see how it was a turning point in my faith and my life.

More here: What to Expect on Your First Solo Trip

 2. The Solo Trip

Trust me, you can do it! My trip to Japan was my first ever solo trip. I couldn’t read road signs or understand the language (though I surprised myself when I quickly learned enough Japanese to get around), and I loved how it made me feel: empowered! You don’t have to go to a place where you don’t speak the language, though. Anywhere out of your hometown or home state counts. Not so sure about that?

Check out my Solo Travel page for tips
and encouragement to give it a go!

 3. Girls-only (or Boys-only)

Sometimes you just need to getaway with a friend! I’ve taken trips to the Bahamas; Asheville, NC; St. Augustine, FL; and Paris with my girl friends, and we always have tons of fun! In 2009, my fiancé broke up with me a couple of months before our wedding, so I had this whole honeymoon trip booked (that I paid for in advance!) for a seven-day cruise to seven islands in the Caribbean. I asked my friend who was going through a divorce to come with me, and we lived it up island style all week long! Never waste an opportunity–just go!

More here: 10 Reasons to Island Hop the Caribbean

4. A Challenge Trip 

Odds are, there is something out there you do not want to tackle. For me, it was the cold. So what did I make myself do right after college? Go to Alaska in the winter time! I went ice climbing, camped on an ice-covered lake, flew a two-seater airplane, and ate Alaskan salmon–in Alaska! I conquered the cold and survived with only 4 hours of daylight each day. I discovered I CAN do anything I want, and I had some of the best sleep of my life. Take a trip to truly challenge yourself, and you’ll realize just how awesome you are!

 5. The Dream Trip

Have some place in mind you really want to go? Take the energy and fearlessness of your 20s and make it happen. For me, it was Australia. Ever since I was little, I wanted to see an opera at the Sydney Opera House and swim at the Great Barrier Reef. When I turned 28, my then-boyfriend (now husband!) made my life-long dreams come true! I realized that even though it seemed like a distant unattainable dream, it was within reach! By the way, I already knew he was the man for me, but he proved it because he paid for two hotels rooms each night. The good ones are out there!

More here: What to Know Before You Visit Australia

 6. A Trip with a “Grown-up” Friend

There’s something to be said for taking a trip with your peers, but it’s important to maintain friendships with people a few (or many!) years older than you. We can learn a lot from people who’ve lived through their 20s and beyond, and believe it or not, they’re a whole lot of fun! My friend Brenda and I went to Boston for a weekend together, and we had a blast!

 7. The “Risky” Trip

By risky, I don’t mean stupid! I just mean you should go to a place that makes people say, “Why would you want to go there?” And then go without listening to anyone’s criticism. I went to Turkey for two weeks with my friend Andrea and a friend of hers from college, and while it had never been on my short list of places to go, it is now one of my most memorable trips!

We saw the ancient ruins of Ephesus (like in the Bible), I took a hot-air balloon ride over the Fairy Chimneys, and we took a boat ride on the Bosphorus Straight between Europe and Asia! Throw a dart at a map, ask a friend where they want to go, or do an Internet search for the top 10 places to go in the world and pick one you never considered before. Then make it happen!

Check it all out on my Turkey Page!

 8. A Long-term Trip

I’m not talking years, just a few months will do. Truly immersing yourself in a culture (or a variety of cultures!) for 4-12 weeks will open your eyes in ways a weekend excursion or weeklong in-and-out vacation just can’t. You’ll have to figure out grocery shopping, living arrangements, toiletries, some of the language, and more, and it will make you feel like you can do anything! Spending three months in Japan was such an eye-opener. You can do it! Just remind yourself that people live there every day–and you can, too!

More here: How to Plan Long-Term Travel in Europe

 9. A Visit to Faraway Friends

Solo travel rocks, but it’s also good to experience a new place with a trusted local–you’ll get an experience you couldn’t get just being a tourist! I’ve visited friends in Alaska, Switzerland, Turkey, and Japan–actually, in all of those cases, I visited friends of friends, and I’d never even met them before! Seriously, just go. Think you don’t know anyone abroad? Ask around. Brainstorm. Know people in the military? They move every couple of years!

This might help: How to Find Cheap Flights

 10. The Heritage Trip

Where did your family come from way back when? What is your heritage? Go there and see how those people lived before they emigrated. What was going on in the homeland at the time they decided to move?We’ll find out more about ourselves when we understand our family’s past. Part of my mom’s family moved from the Heidelberg area of Germany to Virginia in the 19th century, so visiting Heidelberg (and their incredible Christmas markets) was so exciting!

More here: 10 Reasons to Visit Heidelberg

 11. The Educational Trip

OK, this is not as boring as it might sound! This could be a study abroad program, a class located anywhere in the world on any subject, or perhaps even teaching abroad. Teaching English as a Second Language is pretty easy anywhere in the world, since the only requirement is that you are a native English speaker!

Related: 10 Trips to Take in College

 12. An Exotic Trip

What does exotic mean to you? What do you envision when you think of an exotic location? Go there! It might be Alaska, or it might be Rio, but wherever it is you should experience it! For me, islands are the ultimate in exotic. Check it out–the wavy Atlantic to the left, the calm Caribbean Sea to the right:

Keep reading: The World’s Most Epic Landscapes

 13. Island Hopping

You can do this on a plane or on a cruise, but however you do it, enjoy it! When my girl friend and I took our 7 islands in 7 days cruise in the Caribbean, it was fascinating to see how unique each island was compared to the others. All beautiful, but all different! Make it your mission to find the differences and enjoy them!

St. Kitts has twice as many monkey residents as people, and Dominica has amazing black sand beaches. Relatedly, the Big Island of Hawaii has an active and constantly flowing volcano, while Kauai is the oldest of the Hawaiian Islands and its volcanoes went extinct hundreds or even thousands of years ago, creating different terrain within the same archipelago.

More here: How to Choose Which Hawaiian Island is Right for You

 14. Experience an Old World

In our world today, we are bombarded with the newest of the new, instant gratification, and “breaking news” every minute of the day on our social media. Challenge yourself to explore thousands of years of history in Japan, Egypt, Greece, the Baltics, or Turkey. Especially for Americans, it’s amazing to see things that are so much older than our country!

 15. Check Out a New Hemisphere

Go Down Under! Or if you’re already down under, go up top and see how it is for a while! Does the toilet really flush the other way? Only one way to find out for yourself! Experience the opposite season, challenge the things you think you know. Change it up completely!

 16. A Celebratory Trip

Travel is always a celebration for me! But it’s extra special when you go somewhere for a bachelor or bachelorette party (yours or someone else’s!), a birthday, graduation, or special anniversary. A year after foot surgery, I celebrated my left foot at the equator in Ecuador! There is so much about life to celebrate, so find a destination that’s meaningful to you and go!

 17. A Hostel Trip

I’ll admit, I am not the biggest fan of hostels. I’ve had a couple of negative experiences, but I’ve also had a couple of positive ones! I stayed in hostels on a two-week solo trip through Eastern Europe. Other than the naked man on the terrace in Bratislava and the yelling hostel owner in Krakow who insisted I hadn’t paid yet when I had, the other hostels were actually fun! I met some great people who also love to travel, and I got to stay close to the city center on the cheap! Seriously, hostels are sparse, but they’re not that bad… and I appreciate staying in a regular hotel now!

Hostels will help you meet people, but also help you appreciate experiences like this: Legendary Hotels of the World!

 18. A Luxury Trip

Alternatively, save up for a night in real luxury and see what it’s like! Reward yourself after a few nights in hostels with a fancy dinner and a night at a hotel with a spa. If you really don’t think you can afford a luxury experience, take a look at hotels in Southeast Asia–they know how to do luxury right, and the area is generally known for being affordable. Check out discount websites and do some Internet searches for luxury hotel deals! Show yourself that you’re worth being treated well.

Get the deets: Staying at the Royal Hawaiian, Waikiki

 19. An Event Trip

What kind of event? That’s up to you! See your favorite musician in a place you’ve always wanted to go. Run a marathon in a far-off land. I met my husband in Prague just days before he ran the Prague Marathon with a mutual friend! Celebrate New Year’s in a new place. See how another country celebrate’s their independence or other national holiday. My Love took me to the opera… at the iconic Sydney Opera House!

 20. A Family Trip

Enjoy some time with your family. By the time you get into your twenties, your family should be starting to see you as an adult. Instead of visiting them at their home–perhaps the one you grew up in, staying in your childhood bedroom–meet up at a destination to level the playing field so no one has “home court advantage.” Explore a new place together as a family, proving yourself as an adult but also walking your family into the idea that you’re a grown-up, too! I met up with my mom and younger brother for some fun at Green Gables in Prince Edward Island and Halifax, Nova Scotia, and we had a ton of fun!

Did I miss one? Have you taken one of these trips already? Feel like you’ve missed out because you didn’t take one of these trips and you’re already into your 30’s, 40’s, or 50’s? Never fear! Pick one of these trips and make it happen!

Want more trip inspiration? Check out my Travel Tips Page!

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