I’ve travelled solo, with romantic partners, with besties, and in groups; good and bad trips, domestic and international. And what I’ve found is that what happens on a trip—the things I do, see, and enjoy—vary greatly based on who you have with you. You can’t always choose who comes, but you can always choose who you ask!

If you’re new to travel, and looking to branch out into taking trips but aren’t sure if you should do it alone or with a tour group—I’ve got you covered. My advice is first, ask yourself:

What do I want to get out of this trip? For example:

I want to explore the local ruins and museums.

I want to rest and read books by the pool, and come back refreshed.

I want to let loose; bar hop and go dancing!

I want to go hiking as much as possible.

…and so on. Of course, this isn’t an exhaustive list; people travel for a hundred reasons. You might have multiple goals in travelling—like, I want to visit a specific art gallery, spend time eating at nice restaurants, and go shopping. Try writing down all the things you’re looking forward to—things that you’ll be disappointed if you don’t get to do on your trip. Defining your reason for travelling is the fastest way to figure out how to make a great trip happen.

Once you’re clear on this, ask yourself—is this something you want to experience with someone else?

The benefits of solo travel

I’m very pro-solo travel; you get to wake up when you want, spend your days doing whatever your heart desires; lends itself to spontaneity in a way that doesn’t involve another person, and makes compromise a non-issue. I also find that when I’m on my own, I’m more challenged to depend on myself instead of others; having to figure things out solo builds the confidence that you can handle whatever challenges life throws your way. I often come back from solo travel feeling like I’ve learned something new about myself (as well as the world!).

With that in mind, solo travel can also have some drawbacks if you’re not used to it. It can be more expensive when you’re not splitting the costs of a hotel room, or getting a group rate on an excursion. There’s safety in numbers, and being aware of your surroundings becomes much more important when you’re solo. There’s also the loneliness factor (sometimes there are ways to combat this—check out my post on Building Community While Travelling).

The benefits of partnered / romantic travel

If you’re travelling with someone else, it’s inevitable that there will be compromises. But there can also be joys in travelling with another person!

If you’ve got a romantic partner, there are so many reasons why travelling together is a good idea. You get to see your significant other in new and different situations, including how they react in unfamiliar places; how they handle jetlag and international cuisine; how adventurous they’re comfortable being in new countries; or how much walking is “too much”. Many things seem more romantic abroad; a dinner out is now a candlelit meal in Paris; a sunset on the beach is an emotional experience because you’re in Bali.

Having said that; as romantic the potential can be, there’s also the potential for things to go pretty poorly. I know people who have been dating who took trips too soon, and it pretty much ended the relationship. Limited space, cramped quarters, unfamiliar cuisine, a gap of space between the floor and the door to the toilet where you can hear everything that goes on in there—all these things have the potential to be very, very unromantic. Approach this situation with your eyes wide open!

The benefits of the singular Travel Buddy

Of course it doesn’t need to be a romantic partner you’re travelling with; some of my best trips have been with just one other friend!

Unlike a group trip, having just one friend will mean that you’ll be pretty influenced by their wants and needs during the trip. In the planning stages, you’ll probably be able to have deeper conversations about what you’d like to do, and you’ll be able to see if their “list” matches yours. If it does, great! But you’ll be able to tell if there’s a mismatch if the lists have almost nothing in common with each other. If one of you wants to enjoy the spa at the hotel together and the other wants to explore the city, one of you might be disappointed. There’s always room for compromise, though; especially if you’re comfortable splitting up and doing things as singles at different points in the trip.

The benefits of group travel

In my experience, a group trip comes about in one of a few ways, but normally follows a sequence of events: Someone finds a reason to go somewhere (a bachelorette trip; a Taylor Swift concert; a destination wedding; “check out this crazy hotel, we have to go!”), and suggests it to the group. Then the most organized person will come up with some Airbnb or hotel options that will float around the group; one will be picked and booked.

Some of the trips that I’ve taken with groups have been awesome, all centred around people I know well and appreciate. I find it works best when expectations are set early (“It’s Kayleigh’s birthday and she loves to relax, so I figure this will be a weekend to chill, visit the village, and go on long country walks!” is a good heads-up for anyone who thinks that this excursion will be a non-stop party), and that the expectation to RSVP has no pressure attached, as no one wants to be stuck with a roommate who doesn’t want to be there. It can also mean that expenses are split many ways, which can make for a cheaper trip.

I won’t lie; the group trips I’ve been on have sometimes been chaotic, but the chaos is worth it to get a big group together. As someone whose default setting in friend groups is, “whatever makes everyone happy”, I find it hard to stick my neck out and say “I want to do X or Y”, and I find that I tend to go along with what everyone else wants (this is sometimes what you need though—someone says “let’s play hide and seek in this old Victorian mansion” and you need someone else to say “Sure!).

Going with the flow also helps because of the organizing that has to happen to get a group of people together—the biggest group trip I’ve taken was with 18 friends, and figuring out how we’d all be fed meals was an undertaking in itself, between cooking and reservations for groups of our size.

There can be difficulties when it comes to travelling in large groups, including logistics and costs (my favourite app is Splitwise for expenses shared between people!). It can also be tricky if you’re someone who gets social anxiety. I’ve been on trips like this where I feel overwhelmed and want to take some time out, or go to bed early; but sometimes finding quiet is difficult if you’re sharing a room.

Truthfully, I love a group trip—but I’ve found that the more I travel with big groups, the point isn’t “I’d like to see a place” as much as it is, “these people mean a lot to me, and we’re coming together as friends somewhere cool”. If you’re leaning more towards wanting to see a place and want a big group around, there are companies that will arrange group tours on international trips; you’ll be with a group of strangers, but you’ll probably walk out as friends!

By now (hopefully!) you’ve got some food for thought about the company you could keep on this trip. Now’s the time to go back to your list—think about the things you want to do at the place you’re looking to go. Imagine what it would be like there solo, with a partner, a best friend, or a large group. What picture looks the most like what you’d want to experience?

No one can make the decision for you, but hopefully by thinking through the dynamics of having others involved, you’ll be able to make the choice that works best for you.

I want to hear all about the trips you plan—happy travels!