20 Trips to Take in Your 20s

It’s so easy to go on the exact same trips while you’re in your 20s. Many people fall into a certain type of trip, and then just keep going on it because it’s fun and easy. But your 20s is the perfect time to push outside of your comfort zone and expand your travel repertoire. Instead of always going on a group bus trip through Europe, your annual family vacation to Florida, or a road trip with your pet, check out 20 different trips to take in your 20s.

For most of us, our 20s are a time in our life when we have a little bit more freedom. We have some space to figure things out before everything gets set in stone. For most twenty-somethings, we don’t have to worry about finding a babysitter, getting someone to pay our mortgage, dropping out of school, asking our parents’ permission, arranging pet care or pausing our subscriptions before heading off on our annual two week vacation from work. And even if you do have to deal with some of those things in your 20s, they might not be as rigid as they were for generations before us.

Of course, this list isn’t exclusively for twenty-somethings. If you’re in your teens, 30s, 40s, 50s or beyond, there’s still a lot of awesome trips on this list that you might want to take. But if you are an avocado-toast-obsessed twenty-something, these are definitely the trips to take in your 20s.

1) Solo trip

The number one trip to take in your 20s is a solo trip. I’m a huge fan of solo travel – even if you have a partner back at home. It’s the kind of trip that pushes you outside of your comfort zone. Suddenly, you have to rely on yourself for everything from navigation and itinerary planning to staying safe and avoiding loneliness. It’s scary, but it’s also incredibly rewarding. You learn so much about yourself and you don’t have to waste trip time doing things you hate just because someone else wants to do them.

Not sure about solo travel? I get it. It can definitely be scary. But many people have done it before you and I guarantee you can do it too. If you’re unsure about your destination, check out the best place to go for your first solo trip, as suggested by a group of 30+ travel bloggers!

2) A trip with your parents

Another very important trip to take in your 20s is a trip with your parents. Now that you’re both adults, this is going to be a very different trip than that time you went to Disney as a family when you were five. This is your chance to connect with your parents and actually talk to them. They get to see you as an independent and capable adult and you get to see them outside of their role as “mom” or “dad.”

Some of my favourite travel memories are trips I took with my parents. I love my mom’s sense of adventure and brain for planning (I wonder where I get it from?) and had the best time visiting London, Amsterdam, Germany, Croatia and Montenegro with her back in 2014. And I really enjoyed taking my dad to Europe for the first time and introducing him to Amsterdam and Paris last year. And we’re now less than a month away from our big Europe trip with my mom and Colin’s mom!

3) A trip with your best friends

Taking a trip with your best friends is one of those epic 20s bucket list items. It can be so hard to arrange everyone’s schedule and find a trip that works for everyone’s interests and budgets, especially if you’re all living in different places. That will only get harder as you get older. So take advantage of your freedom in your 20s and prioritize hanging with your besties. You don’t want to let these friendships slip away. Now that you’re all growing up, working on your careers, getting married, moving away or starting families, it’s important to find time to be together.

And once you start this tradition in your 20s, hopefully it’s something you can continue for years to come!

4) Camping trip

For some of us, a camping trip is pretty far outside of our comfort zones and for others, there’s nothing easier than going camping. That’s the beauty of this list of trips to take in your 20s – every trip is different! For me, camping isn’t my greatest strength. I don’t love to pee outside and I really hate the idea of having to pack an entire car full of stuff even if you’re only going for two nights.

But I love roasting marshmallows on a fire, looking up at a bright night sky, turning off my phone for a few days, and spending time admiring the views or playing card games. Some of my favourite trips from the past few years have been our camping trip to Porteau Cove and our annual camp at Pender Harbour.

5) Treat yo self trip

If the idea of going camping makes you shudder, you’re going to love this next trip. In your 20s, I think it’s important that you go on one Treat Yo Self trip. This is a trip that is luxury and makes you feel first class. Note, this trip only has to feel like a luxury trip, it doesn’t have to have a luxury price tag. If you’re on a budget, you can still treat yourself to some luxury by going to a place where your dollar goes farther or by only spending a couple of days in paradise.

For example, our budget was able to stretch pretty far when we were in Southeast Asia. I know it’s not luxury to everyone, but we certainly felt like we were treating ourselves when we got to sleep in giant beds and hang by a cool pool in Siem Reap, Cambodia. So many people hold off on fancy trips, thinking they have to be filthy rich. But you can still treat yo self on a budget!

6) Challenging trip

This is going to look different for everyone, but I think it’s so important to go on a trip in your 20s that challenges you. Of course, we all love going on fun and relaxing vacations. But I think most of us also travel to grow, to learn about the world, to discover new things and to change who we are. That won’t happen if you don’t challenge yourself.

For me, a challenging trip that I hope to go on one day is a trip to India. I know I’m going to be uncomfortable with the poverty, the overwhelming sounds and smells, Delhi belly, navigating and so much more. But it’s a trip I want to push myself to take and has been on my travel bucket list forever. Other trips that challenged me this decade were the summer I interned in Swaziland as a “psychologist” and my big miss trip to China.

7) Staycation

A staycation is a trip you take in your own backyard. Treat your city like a tourist and do all of the things you take for granted while living there. You can even make it more fun by booking yourself into a hotel. Staycations are a great way to appreciate all of the awesome things to see and do in your own city, save some money, and feed your wanderlust when you’re unable to go on a big trip.

A few years back, Colin and I had a great staycation on Granville Island in Vancouver. I had won a few nights at a hotel and it was really fun to hang out on Granville Island, see a show and feel like tourists in our own city. We also did a staycation/weekend trip hybrid when we headed up to a log cabin in Hope and spent the whole weekend watching movies and admiring the view!

8) Back to somewhere you love

These days, there’s such a priority on new-ness. Everyone wants to do something new, be the first one to do something, and tick another country off of the bucket list. So what’s the point in revisting a country you’ve already been to?

There are actually a ton of reasons to go back to somewhere you love. You get to know that place more deeply, appreciate how a place changes over time and slow your travel. Plus, I love the idea of having that place that you go back to every few years. For me, that place is definitely London and I can’t wait to head back again soon.

9) Shitty trip

Listen, at some point in your life, you’re going to go on a shitty trip. You’re going to have a trip that’s full of mishaps and mistakes, you’re going to hate a place, and you’re going to have bad travel days. Might as well do it in your 20s!

That’s not to say trips in your 30s, 40s and beyond won’t have their share of mishaps too. Unfortunately, there’s no age limit on shitty trips. But your 20s is a great time to dive head first into these mistakes and learn from them. Hopefully the mistakes aren’t too grave and you can bounce back from them. Take your learnings from this shit trip to make your next trip better.

10) Something all inclusive

A lot of older people fall into a trap of only visiting the same all inclusive resort in Mexico every year or only going on all inclusive cruises. So why would I recommend this as one of the trips to take in your 20s? Because you shouldn’t knock it before you try it. It turns out, all inclusives can actually be kind of fun. There’s no pressure. You don’t have to plan anything and it’s a great way to really slow down and relax.

Of course, you don’t have to make this your new mode of travel. While I have enjoyed a cruise or resort in the past, it’s not my preferred trip. I would much rather be moving around, interacting more with the local culture and planning my own itinerary. But I see the value in an all inclusive and am glad I’ve had the opportunity to try a few out.

11) Budget trip

This is likely the trip that most twenty-somethings can already check off the list. Of course we’re going to be doing a lot of budget travel because we’re broke (hello, student loans and entry-level jobs). Budget travel can be a lot of fun. You don’t have to sacrifice the quality of your trip just because you’re pinching your pennies.

The best way to go on a budget trip is to choose a cheap destination and get a great flight deal. Bacpacking across Southeast Asia, staying in dorms in the hostels of Europe, or couchsurfing across North America are all great budget trips for your 20s.

12) Weekend trip

Mastering the art of a weekend trip is an important skill to acquire in your 20s. With a weekend trip, you’re short on time so need to learn how to make the most of what you have. You have to choose a nearby destination, so you don’t spend half the weekend getting there, and a place with enough to do but not too much. The perfect weekend trip helps to shake up your home life and feed your travel-addiction, without being too boring or too stressful. We had the perfect weekend trip to Dresden from Prague!

As you enter your 30s and beyond, weekend trips might become a better option for your life. When you have to deal with the constraints of full-time jobs, your partner’s schedule, children in school and other obligations, you might only have a weekend to get away. In your 20s, learn how to make the most of it.

13) Well-planned trip

If you’re used to going on group trips, hiring a travel planner, or leaving the itinerary up to your friends or family, it’s time for you to push outside of your comfort zone and plan your own trip. A well-planned trip is one that takes some time and research. It means scouring the internet for the best flights, hotels and things to see, do and eat.

For some of us (me), being in the planner position of a trip is a natural fit. I love planning trips. I love creating spreadsheets, looking up flights, reading through travel blogs and coming up with the perfect itinerary. But if you’re not used to this role, it’s important to give it a try, step up and take responsibility for your travel.

14) No-plan trip

On the other hand, I also think it’s important to go on a no-plan trip in your 20s. This is the exact opposite of a well-planned trip. This trip is spontaneous and you fly by the seat of your pants. As a planner, I have to admit that a trip like this makes me nervous and I haven’t been on too many.

But I do love the idea of letting a place surprise me and just winging it each day. By doing both a well-planned and a no-plan trip in your 20s, you can find the perfect balance between planning ahead and being spontaneous that you want to take into your future travels.

15) A trip that lets you down

Unfortunately, you’re not going to love every trip that you take. Sometimes you’re going to hate a place. You might have heard great things from friends about their trip to Paris, fallen in love with photos of Peru on Instagram or always imagined you would fit right into Singapore life, and then be utterly disappointed when you arrive.

That’s okay. Trips are sometimes overrated and will let you down. You thought it was going to be one thing but it turned out to be something else. Try to make the most of it and apply the lessons from this trip to your next one.

16) A trip that impresses you more than you thought it would

On the other hand, sometimes a trip that you had no expectations for (or even one that you were dreading) can turn out to really surprise you. An underrated trip is a great one to take in your 20s because it shows you that you can’t knock it until you try it.

I managed to tick off both trips #15 and #16 back in 2014 on a visit to Switzerland. I was convinced that I was going to love Geneva, but it ended up being really expensive and kind of boring. Plus, our train reservations fell through so we never made it to our next Swiss destination. Huge let down. On a whim, we decided to take a bus to nearby Annecy in France, with no clue what it would be like. And it became one of my favourite cities in Europe! This charming and beautiful French town totally impressed me.

17) No trip

A big lesson to learn in your 20s (that I’m still struggling to learn) is that you can’t always say yes. As someone who spends a lot of time reading travel blogs, looking up flights and interacting in travel groups, both for my personal interest and for my work, it can be really hard to say no to a trip. “But the deal is just so good!” or “I’ve always wanted to go there!” I’ll tell Colin.

But sometimes we have to prioritize other things in life. Sometimes the trip we have to take is actually no trip at all. Even though it looks like everyone on social media is running off to a new, beautiful destination every other day, that’s not real life. We all have commitments, budgets and non-travel goals we need to respect too.

18) Travel hacking trip

If you’re in your 20s in this day and age, it’d be silly if you weren’t making the most of all of the great travel hacking options available to you. Gone are the days of waiting to meet with your travel agent at the mall who would do all the bookings for you. These days you can do the research, find the loopholes and book everything online.

There are lots of great ways to get into travel hacking and save money on your trips. I’m a big fan of finding cheap flights and saving money on accommodation by earning free hotel nights or using Airbnb. You can also couchsurf, house and pet sit, or volunteer to get free accommodation. There are loyalty programs, airline miles, credit card points and so many other ways to hack your travels.

19) A trip back home

If you left your hometown to head off to school or work, an important trip to take in your 20s is a trip back home. I left Toronto in 2010 to attend university out in Vancouver. And while I didn’t officially start calling Vancouver home until years later, I think I knew then that I wasn’t coming back to Toronto. Almost a decade later, and I’ve spent most of it living in Vancouver and now, living in Prague.

Going back to Toronto and visiting with my family is important to me. I have lots of family and friends back home and it’s hard to keep up with everyone. My favourite time to go back is over Christmas when it’s just a blur of family events and way too much food. It’s chaotic and crazy but it’s also the best way to see everyone all at once.

20) Wedding trip

Let’s be honest. You’re in your 20s so a wedding trip (or seven) is just inevitable. This is the decade where half of your trips will be flying all over the place to attend weddings, showers and bachelor/bachelorette parties. Better start earning those airline miles!

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And there you have it, the 20 trips you should take in your 20s. Of these 20 trips to take in your 20s, how many have you been on? Which trips are you excited to go on?

 

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