To travel with friends or not to travel with friends. That was a question this solo traveller asked herself in August and very quickly decided, yes. Travel with friends. But in the lead-up to the trip, a little worry sat in the back of my head.
To Travel with Friends
It has been years (more than a decade?) since I’ve travelled with a group of friends. I mean, I travelled with fellow vanlifers Katie and Dan to Guatemala, but that’s different. They’re a married couple and I obviously would be the odd one out. (For the record, they were awesome to travel with, even as the third wheel!) Writing this, it’s wild to think of how long it’s been since I’ve travelled with a friend group. I was nervous.
Typically when people are unsure about group travel, they wonder how others will mesh with their own travel style.
That’s not what worried me. I was concerned that I would be the odd duck.
That I wouldn’t mesh well with them, or any group for that matter. I’m so used to doing everything on my own and my trips tend to be more work than play these days. It’s not that I wouldn’t want to go with the group flow, but I knew I’d be working remotely and not exactly in vacation mode like the rest.

Spontaneous Sparks
Before recapping the trip itself, the story of why and how this trip came together is pretty incredible.
You know those friends you always say, “we should go on a trip” with and then it never happens?
These friends, apparently, are the complete opposite!
It was a perfect July evening. A few of us were enjoying a night of live music outdoors, first at a surprise show and then at a local music festival. It was one of those magical summer nights that leave every fibre of your being buzzing. That high vibration energy often appears on the road. At home, its unexpected appearance doubled the giddiness.

Unbeknownst to me at the time, a friend who couldn’t make it out that evening loves Elton John. This factoid is relevant because an Elton John tribute band was playing at the music festival. Enthusiastic friends that we are, we caught the set so we could (boogey and) send them videos to enjoy the music at home.
After the festival, 3 of us were chilling outside and someone mentioned that Sir Elton was playing an upcoming show in Mexico City. A covid make-up tour. Jokingly, the idea was tossed out to catch the concert. Google was searched. Tickets prices reasonable. We eyed each other to gauge if this was more than a whimsical idea. One of us, who’s from Mexico, would already be there visiting family and friends. I had not yet been to Mexico City. The other friend is half Mexican and loves live music.
Things were getting serious. Fast.

Between that late night pizza hangout and 4pm the next day, the rest of our puzzle piece crew gathered for an impromptu brunch. Would the other 3 be in? Was this really going to happen?
By 3:54 pm, tickets were purchased. It was official. We’d be travelling to Mexico City to see Elton John!
I’d say we shocked ourselves right up until departure day. The serendipity of everyone being available (a miracle in and of itself), saying yes, and booking pretty much on the spot was so fabulously out of left field. Even as a well-travelled group, we kept exclaiming over the timing of it all. When does that ever happen?! It felt like being 20-something again and man, was it exhilarating.
The joke of it all was that not one in the group, except for the aforementioned friend, was an Elton John fan. Sure, everyone knows and enjoys dancing to his music. But lyrics? Fun facts? A burning desire to see him in concert? Nope.
What made this trip happen wasn’t a shared love of the performer. It was a mutual zest for life, exploring the world, and spontaneity.

The One Where They Go To Mexico City
Airport Lounges
Three of us arrived in Mexico City earlier in the week. The rest were coming for the weekend. With two of us having the ability to work from our laptops and the other with a flexible schedule, why not extend our stay?
My fellow remote worker is also a points and miles aficionado, albeit the sort that loves lounges, access perks, and so on. In the points world, I’m an anomaly. I fly economy and don’t care for bells and whistles. Much of it is wasteful and, in my not so popular opinion, unnecessary. The entitlement and elitist sentiments I’ve observed in certain points conversations irks me too – but to each their own!
It was my first point of internal tension on the trip. Join the herd or do my thing?
Would I be that person who splits from the group due to personal preference before we even leave the airport? Begrudgingly, I followed through the VIP doors after putting up a little resistance. I got a petty kick out of the fact that we waited half an hour to enter the lounge, despite our friend’s previously declared dislike and avoidance of lines at the airline’s check-in. Smug is not my proudest look but, admittedly, I tried it on for a few minutes.
Through the gilded doors, I left the other 2 to hop on my laptop, fill up a little plate with food, and tap tap away at work. I know what you’re thinking – who’s the party pooper working on a group trip? But I had deadlines to meet and knew my schedule would be chopped up during the week. Plus, there’s something calming about working in an airport. Maybe it was the super dim lights in the lounge…
You know what the true highlight of the pre-flight experience was? My swanky new(ish) black sweatpants. Shockingly, they fit like an average-sized human’s (re: not flood pants). As much as shorter pants have been “in” the last few years, my inner child refuses to accept this trend. Growing up, having pants that were too short was not cool. Those who’ve embraced this short pant trend are clearly beneficiaries of AHP or Average Height Privilege. I haven’t had a matching sweats outfit that fits since I was in Kindergarten. No joke. This 6-foot woman was on Cloud Nine! I have never felt so cool.

Sardine Rides
Our red-eye flight was delayed by quite a bit. Luckily, I can sleep anywhere and still banked a few winks on the plane. Exiting the airport around 1:30am, after waiting for the only Priority-tagged bag in our group (*stifles laugh), we got into the funniest Uber ride ever.
Picture this:
Me, 6-feet, the remote worker, 6’2″, the flexible schedule friend, teeny tiny. Two medium-sized luggage, 1 carry-on suitcase, 3 backpacks, 1 hot pink cowboy hat. And a Chevrolet Spark. The look on the driver’s face when he saw us was priceless. Determined and clearly a “yes man” (unlike the SUV driver later in the week who left us stranded after a half-arsed loading attempt), he wordlessly packed up the vehicle with luggage split between the front seat and the barely existent trunk. In an instant, the 3 of us became much closer friends, sitting on top of each other to close the doors. The car very slowly chugged along to the Airbnb, steadily humming it’s own “I think I can” mantra. We sleepily giggled the whole way.

First Impressions, 101 Dalmatians, and Busker Observations
I have often said that first impressions don’t hold much weight. More often than not, they’re inaccurate (re: incomplete) representations or not so memorable. Mexico City, however, has rizz. From its lush and leafy calm streets in Roma Norte, to the abundance of bookstores and book-themed cafés, to the variety of artful details in bricks and doorways and trees, to the rolling Spanish tongue, our first 24 hours together were captivating.
All 6 of us remarked at some point during the trip at the number of (very well-behaved) dogs in Mexico City. The street scenes reminiscent of 101 Dalmatians; pet owners strolling with their pups and dog walkers leisurely minding groups in the park as if enjoying a casual café catch-up.

On more than one occasion, I observed how people treated buskers differently than at home. Instead of sonic wallpaper to be consumed sans acknowledgement, café patrons were kind, thanking and tipping the musicians as they came around to each table, hat outstretched for their talent and time. People of all ages reciprocated the musicians’ efforts. I want to know more about this admirable part of Mexico City’s culture.
On the other hand, the choreographed carpet sellers were paid no attention.
Bookstore Cafés and Details
My favourite part of Mexico City was the continuous reveal of book shops and bookstore cafés. Some streets housed inviting secondhand sellers, dark and crammed and alluring with the scent of aged paper and ink. Others featured colourful, trendy shops and cafés. There was even a library speakeasy!
For half of the week, I hunkered down to work in bookstore cafés. It’s nothing short of a miracle that I accomplished anything and didn’t leave each day with my arms full. Honestly. If there’s any hope for the (human) written word (in print, no less!), it’s in Mexico City. I was in heaven. For this trip I researched nothing. You better believe that any return visits will be well-planned explorations of every fascinating book nook.

Another simultaneously striking, yet subtle, aspect of Mexico City that I adored was its endless detail. Intriguing and beautiful intricacies covered every surface. The bricks. The doorways. The sidewalks. The trees. The trees! Oh my, the trees. The whole city is an art piece. One could visit Mexico City, forego all of its impressive museums and, instead, walk the neighbourhoods, observing and absorbing its elaborate surfaces and layers. Little peekaboos. Bold craftsmanship. Intention. Semiotics at play. Yum!
Some of my favourite moments in Mexico City were spent meandering at my own pace. The only thing missing was my camera to document and exercise my own creativity. Next visit. This act of walking and observing, or sitting and observing, is truly one of my favourite activities.
Art collectives seem to be quite popular in Mexico as well. I stumbled upon several galleries and shops, many of which belonged to co-working artists. Another fascinating statement on local culture.
Fancy Gulps
Our lounge-loving friend is also an amateur foodie and verified cocktails connoisseur. Their worldwide travels, including a previous Mexico City jaunt, are often gastronomic in nature. Said gustatory enthusiasm accompanied us. Our friend organized visits to their favourite spots, with a few new cocktail bars added into the mix. On one night the theme was speakeasies, another was books. Both are up my alley, though I’m less magpie, more flamingo or chickadee. Glitz and coveted reservation lists are less enticing than the quirky, common, and overlooked.

Enter the second point of personal tension.
It’s funny. At home, I often wish there was more nightlife. I enjoy a good buzz, getting dressed up, and experiencing new spots. But, when presented with (a plethora of) options to do so in Mexico City, I wasn’t nearly as keen. Part of that can be attributed to being locked in to work mode. No room for hangovers when deadlines are looming. Unlike my salaried compadre, I don’t get paid if the work isn’t completed and the client unhappy. I had also recently resumed my fitness routine after nearly a month on the road. Sluggishnish was not on the itinerary. On the road alone, I also rarely drink and never seek out bars. As a solo female traveller, it’s a risk I’m not willing nor wanting to take. My enthusiasm for back-to-back-to-back bar hopping nights quickly waned.
So, what was the resolution?
The great thing with group trips, though we were only 3 for the first half, is that (depending on dynamics) not everything has to be a shared activity. I teeter-tottered between not wanting our friend to feel alone and honouring my own needs. A quiet night in finishing up some work called my name. I answered and headed for the couch. I felt a little bad when they ventured into the night on their own; our non-working friend had also tapped out. The balance, in my mind, was that the rest of the group would soon join, at which point nights out would resume.
A lot of tacos were devoured during our time in Mexico City – and I ain’t mad about it! One must indulge in the world’s specialties on home turf. Taco stall hopping was the perfect way to practice Spanish and meet new people, both locals and other foreigners. On one such self-led taquería tour we made friends with a solo travelling French man. He subsequently joined us on many more adventures throughout the week. We also met a really lovely vendor named Jorge who introduced us to Glorias, a popular Mexican caramel and walnut candy.
Again, my friends had compiled lists of where to go and what to eat – the best street food stalls, the popular restaurants, the specific tacos “you must try”. Since I’d visited Mexico before and eaten many fabulous Mexican foods on that trip, I didn’t mind the monothematic menus.

While my friends love researching locations before a trip, I typically dive in afterwards. The luxury of sharing the travel mental load was another major highlight (*salutes, IYKYK) of group travel. What do you mean I can leave my bags with someone instead of squeezing myself and luggage into an awkward airport bathroom? Dinner plans? Already sorted. Airbnb research? Done. Wowzas. Those used to travelling with a partner, friend, or family member might not realize the joy and privilege of said freed up brain space, but I definitely did. What a treat!
For me, this was the most “vacation-like” aspect of the trip. Similar to the month I spent in Guatemala, I could relinquish my Type A tendencies and comfortably don my Type B self. I’ve missed that! When you’re not the full-time planner and adventurer, it completely changes the experience.
Their efforts and enthusiasm for the treasure hunt reminded me that advance knowledge can be beneficial, adding a layer of appreciation and awareness to travel that I’ve turned away from in recent years. Sometimes I think I’ve oscillated so far from my plan-plan-plan days into go-with-the-flow and loving the surprise of travel that it’s time to rebalance the scales.
Eltón! Eltón!
As mentioned at the beginning of this piece, the spark that kickstarted this trip was to see Sir Elton John rip it on the keys. For (nearly) an octogenarian, I can confirm, he’s still got it. While Elton’s performance appeared innate and easy, I’ve never exerted more energy to see a concert in my life. It’s a trek between the metro and the uphill walk to the venue. And I was in in heeled boots, no less! It was, however, worth the effort.
Our group dressed the part, with sparkles and sunglasses, glo-sticks, and a whole lot of energy. Our seats, 4th row from the top of the gigantic Banorte stadium, sheltered us from the rain and provided a panorama view. Perhaps the “nosebleed” section needs to be rebranded to the “canopy chairs”.

The stadium, known as both the Azteca and Banorte, is massive. Nearly 90,000 seats! According to the interwebs, it is the largest stadium in Latin America and the world’s 8th largest football (soccer) stadium. I’ve attended plenty of (American) football games at Notre Dame which seats nearly 80,000, but this place felt immense. Part of it was the dizzying ascent to our seats. Steep was an understatement. I don’t know how anyone could be drunk in that stadium and not plunge to their death. Then there was the terrifying “width” between seats. Oh. My. God. I held on to each person I passed for fear of stumbling on a stranger’s foot and going ass over tea kettle down the stadium rows. Childhood me couldn’t climb the stairs with spaces between them for the potato sack slide at Sportsworld. It’s a wonder I made it up and across these concrete tightropes!

Back to the concert. I thought the visuals on the screen were disjointed and weird. AI-like even. Non mi piacciano. But that didn’t matter. We saw Elton John live!
The audience loved him, chanting “Eltón! Eltón!”.
The man directly behind us was his biggest fan. Experiencing a crowd is often just as enjoyable for me as the show itself and Mexico City delivered.
Post-concert, we witnessed rainy season in full force. The stadium lights mingled with the downpour and we became hypnotized by the expansive sparkling waterfall. Mother Nature read the costume memo and delivered its own stunning show. Waiting for things to let up (silly us!), we hung back with other concert-goers despite security insisting everyone leave. Eventually we ventured out into the rainy night, accepting our inevitable soaking.
Tension point numéro 3 (not really…this one’s just for dramatic effect!)
Myself and another friend were wearing new leather boots. Mine, black leather and more expensive than I’d like to admit (a true splurge). Theirs, brand new leather cowboy boots that took a weekend of scouring Mexican shops to find. Both of us refused to tempt fate and have them ruined. Our Mexican friend noted our resolve and convinced nearby cleaners to give us a garbage bag. While some might have worn the bag to shelter from the storm, we dropped our boots into the heavy duty plastic, our friend slung it over their shoulder like Santa Claus on Christmas Eve, and, giggling, we made our way back to the Airbnb via Mexico City’s streets, subway, and an Uber barefoot.
I live for stories on the road (/in life) like this!
The Surprise Day
The day after the concert, our Mexican friend had arranged a surprise excursion. All we knew was when to depart, that bringing snacks and alcohol was suggested, and that their friends from Mexico would be there too. Everyone was super excited.
We split into 2 of their friends’ cars, unaware of the route or destination. Our friend pointed out places of note as we zipped along the highway, leaving Mexico City. The car ride was as much a means of transportation as an opportunity to get to know their friend and them better. Over the years, I’ve come to deeply appreciate spending time with friends in places where they grew up or spent formative years. Whether they lived in other countries or elsewhere in Canada, there’s something very special about spending time with a person in a place and with people that’ve shaped them.

The surprise turned out to be a trip highlight for the whole group.
Green, red, and white flags appeared above the street and we were told that it was close. We arrived at a place called Xochimilco. It’s a cultural UNESCO World Heritage Site, a protected nature reserve, and a living reminder of Aztec populations past. It wasn’t until the parking lot, however that we were informed of the day’s activity: an afternoon of dancing and drinking on the water, floating in a trajinera, or flat-bottomed boat. Amaaazing!

The weather was excellent, the location interesting, and their DJ friend kept the energy bumping. Their friends, from different parts of their life, were all welcoming and a lot of fun. A few of them had been to Xochimilco before and we learned it’s popular with locals as well as a tourist destination. Everyone quickly got to introducing themselves and mingling.
Tension number 4 arose
One of the beautiful aspects of travelling is becoming more comfortable with yourself. Exposure to the world and navigating your way through it builds confidence and self-awareness. Similar to when people go away to school, there’s an opportunity to try on different versions of you – or to reveal what was always there but may have been buried under layers of expectations, self-protection, or conformity. This, I believe, happens because you’re physically separate from family and the community that raised you. I don’t think it can happen otherwise.
I am at a stage in life where I know and am comfortable with myself. I’ve read, watched, experimented, analyzed, observed, questioned, branched out, expanded, made connections, screwed up, retreated, learned, tried again, and done many other things one does in a few decades alive. However, as much as any of us are no longer the people we were growing up, they are a part of us.
When 2 disappointing interactions happened on the boat, it was an opportunity.
The first was a repeat of middle school dances past. I was the only female in our group of friends not pulled onto the boat’s dance floor. I did the internal scan: my hands were empty and I was having fun dancing, chatting, and imbibing like everyone else. Next came 2 questions: 1) If I checked the boxes of being approachable and enjoying the day, what else was I not doing to appear that I would also love to participate? 2) Is this a height thing?
Before you come at me that height doesn’t matter, it does. And if you’re not a 6-foot or taller female, then your opinion is moot. Even in non-romantic situations I have been told all my life that I am “too tall”. To each their own. I wanted to dance, so I initiated with one of the guys. We didn’t dance long and it was fun, though chatting afterwards they mentioned that I am “you know, too tall”. Le sigh. (To be clear, for me none of this was about romantic possibility. More so, it demonstrates a common barrier for tall women.)
The second interaction really surprised me. I was chatting with one of our Mexican friend’s friends, who I also knew from home. They were well under the influence and mid-conversation abruptly changed the topic, asking me why, despite travelling the world and “seeing its passion and fire”, do I not just let go and have fun. It shocked me because I was having an awesome time! I took a pause to think and then asked what made them ask the question. To be honest, I don’t remember their answer! Instead, I proudly recognized what I accomplished. While the thought, “What am I still doing wrong that people think this of me?”, did cross my mind, I responded to them seeking understanding instead of reacting. I also made the decision not to ruminate or let it ruin my day, something which younger me would have found difficult to avoid.
This situation, of travelling abroad yet being with people who know you from home, I think, is an interesting dynamic. The home self remains projected onto you while being whoever you are in your mind at that moment. Perception and reality persisting through whatever stories we tell ourselves and/or have imposed upon us. None of my friends on the trip knew about these tension points on the boat. They didn’t necessarily need to, I suppose. In the same way, I do not fully know how they experienced the group trip. It’s another example of sharing an experience with others and it still being completely different for each person.
Really, these were not tension points. They were moments of success in an already outstanding day.
The day ended with everyone gathering for dinner at a restaurant. We had a private corner area to ourselves, ordered family style, and gabbed away until everyone was ready to call it a night. It was a fabulous way to conclude an already awesome experience. One of their friends returned to the restaurant (they had gone home for a rest) to drive us to the Airbnb. I don’t think I”d ever seen a friend extend that kindness in Canada. Maybe it was a one-off because we were guests. But something made me think that’s just how our friend’s friends take care of each other.
Serendipity on the Last Day
For some bizarre illogical reason, this chocoholic did not seek out any on either visit south. Mexico had me covered though. Luckily, on the last day while exploring Coyoacán with the French nomad and his lovely Mexican Couchsurfing friend, we stumbled upon a chocolate festival. How serendipitous!
The rest of my home group had other plans for our last day. I jumped on the opportunity to do some touristing. From using public transportation, to getting a buzz each time I interacted in Spanish, to making new friends and taste-testing our way through the festival, it was another really fantastic day in Mexico.
Five of the six of us had a red-eye flight home. The sixth, our lounge lover, had departed earlier in the day. Our Mexican friend’s friends drove us to the airport. They stayed and hung out, despite the late hour on a work night, until it was time to go through security. You could see how much they care for and love their friend. I was touched by their actions. Throughout the week we had seen example after example of their hospitality toward us and their warm sentiments towards their friend. This gesture still felt above and beyond.
I was once again struck by something we can learn from Mexico.
Maybe it’s because I’ve never asked. Maybe it’s because it’s only recently been offered. But I have never been taken to or picked up from the airport by a friend. Observing how these friends acted with each other was a wonderful reminder and example that we should be less focused on doing everything on our own. Since returning to Canada, I’ve put into action this ethos several times. I am grateful to have crossed paths with all of our friend’s wonderful circles in Mexico.
Another serendipitous moment occurred at the airport when a security guard near us fainted. One of the drivers is a doctor and attended to the woman until paramedics arrived. It was at that moment, when they switched back to pedestrian mode, that we realized we were at the wrong security entrance. We had to double back. We were in the right place at the right time though.
To Travel with Friends or Not to Travel with Friends…What is the Conclusion?
This was a trip for the books. Scratching the surface of a new location, practising Spanish, indulging on tacos, great weather, chill couch hangouts, the fun of getting ready together, live music, personal growth, nights out, walking tours, new friends, and a whole lot of wonderful memories. I can hardly wait until the next group trip.

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Helpful Tips for Booking Your Trips
My Favourite Travel Resources
From massage balls perfect for post-flight stretching to plant-based luggage freshener to a travel mindfulness guide I created with a local therapy company, here are my favourite travel resources to help you plan and enjoy your own adventures.
Flights
If you want affordable flights, you must get into the points and miles game. Check out my Points and Miles Travel Coaching services to help Canadians fly for less than a tank of gas!
Car Rentals
To help you explore new destinations, turn to Discover Cars for a huge range of vehicle options and excellent prices.
Accommodation
There are so many options for affordable, comfortable, and unique accommodation. Some of my favourite accommodation options are housesitting and hostels. I’ve been using Trusted Housesitters and Hostelworld for years. If you prefer hotels, then check out Booking.com.
Activities
Get Your Guide is a fantastic resource for different activities to try when travelling. They have everything from walking tours, food tours, tickets to attractions, and multi-day trips, and more. Check out this super cool view I had of Tallinn when I was in Estonia for the Christmas markets in 2023, all because of a Get Your Guide experience. My favourite tour so far that I’ve been on with Get Your Guide is a fantastic walking food tour I did in Dublin. That experience had a wild twist, but you’ll have to read this blog post to find out why!


