I’ve never been someone who wants to go on the same trips year after year; I know some people have a favourite place to spend their Christmases or summers, but I always want the novelty of a place I’ve never been before.

Whenever I go somewhere new, I often feel the need to suck the marrow out of every experience. My rationale is: this might be the only time in my life that I’m in this place! I want to see, hear, and experience everything this place has to offer.

But lately, I’ve been revisiting places; in 2025 alone I’ve taken three trips to places I’ve been to before. I don’t regret any of them, or wish I’d opted to go somewhere different or exciting.

One trip was to Ontario, Canada—my partner and I visit Stratford and Cambridge to visit family at least once a year. This is a trip we’ve made at least 5 times at this point, so much so that we have it down to a science; from off the plane to baggage claim, then quick sandwich at the café nearest where we pick up our rental car. We even know what “En Route” stop we’ll be stopping at when we hit the road to break up the trip in even parts (and avoid bathroom disasters).

The point of this trip is always the same: our aim is to spend time with loved ones. The activities we do vary (sometimes it’s outlet malls, sometimes antiquing; once it was theatre) but we’re there to enjoy quality time with our families. So it’s kind of fine, in a way, if these trips feel similar in my memory; the goal of the trip hasn’t changed.

The second trip I re-took this year was to Paris, France. I’ve been to Paris a handful of times, but never under the same circumstances. When I was in my 20s, (and was varying degrees of being broke), I was super lucky to have a friend who lived in Paris that I could stay with.

I once got a ferocious cold, and almost cancelled on her; she was desperate for company and begged me to visit. So I shlepped over, only to spend almost the entire weekend sleeping on her sofa, sick out of my mind. Somehow, that was still fun. Another time, a booking mistake (my fault!) meant that our outgoing train was missed—a friend and I booked a BlaBlaCar and drove with three strangers. Each time, getting there was its own adventure; and each time, a visit to spend time with a friend.

When I went this year, the circumstances were very different. My friend has long since left Paris, and with it, the free accommodation; so not only was this a solo trip, but I was staying in a tiny hotel which didn’t feel very safe. I went with ideas for things I wanted to do, where in previous trips my focus would have been going-with-the-flow. And being in my 30s, I had a bit of money—so I could spring for excursions, tours, and souvenirs.

Lastly, I spent five days this summer in Sintra, Portugal, for a friend’s wedding. The first time I went to Sintra, it was a day-trip with a group of people I’d met in Ericeira—I’d stayed in a hostel where the stay included surf lessons. One person had suggested renting a car to Sintra, and we saw the Pena Palace and not much else. I remember it fondly as one of the cheapest international trips I’ve ever been on, knowing I never want to stay in a hostel with multiple bunk beds in it again. When I went this year, my partner and I were able to afford a decent hotel, and had time and space to enjoy the sights and sounds that Sintra had to offer.

So, why go back somewhere you’ve been before? Honestly, nine times out of ten, I will probably still opt for somewhere new over somewhere I already have memories of being. But if you’re thinking of revisiting a place, consider the following:

What did you feel like you missed out on the first time? There’s nothing more annoying than coming back from a trip, and in telling your friends about it, getting the response of “Oh, did you see the Cool Museum of Awesome Stuff You’d Love?” when you didn’t get the chance (or hadn’t heard of it). What attractions would you experience that you hadn’t the first time?

What experiences would you like to have again? When I was single, there were definitely times when I’d think, this place is so romantic or I’d love to go on a date here. Life circumstances might mean that you’re a different person, who has a different goal in mind for this trip that you want to see come to fruition. Or the place you’re going to might also have changed it’s appeal, depending on the time of year; I’ve been to Calgary, but never when the Northern lights can be seen from the city, and I’d love to go back for that.

Do you want to take a bit of pressure off the anxiety around trip planning? Going somewhere you’ve been before can have a kind of stress-relieving effect; knowing what you’re getting into with directions, languages, and currency can take make some of the challenges that come with travelling obsolete.

Did you have fun last time? The answer doesn’t need to be “yes”! There are trips that I’ve gone on where on the way home, I think, Wow. I was really not present on this trip, or I wish the weather had been nicer, or That carbon dioxide leak really put this break into a tailspin. If you didn’t have a good time, what’s wrong with a second take?

Do you like to take the same trips? I hope you’ll let me know in the comments; and as always, happy travels!