Where to next? The art of traveling with your gang
Adventures get sweeter when you already know who you want by your side.
Do you know what the best thing about being in your 50s is? Well, aside from being financially independent, it is knowing exactly who you want to surround yourself with. By this time, you have already built a circle of people who bring out the best in you. Solid friendships. The kind that do not just last through dinners and parties but through travel, shared rooms, and week-long itineraries.
Finding your rhythm
As I sit here working on this piece, my friends and family, who also double as my travel mates, are in the kitchen cooking dinner. After a long day of hopping between Denmark and Sweden, we come home to a group that, despite their own tired feet, still puts together a warm meal.
My job? I have happily claimed my place in the breakfast and clean-up crew. It is a rhythm we have all settled into, a system that just works.
For the seven days we have been here, there have been no fights for the bathroom, no missed departure times, and no late-night wanderings. At this age, we actually like being home by 8 p.m. and in bed by 10. The energy of our younger years may have dimmed, but it has been replaced by something better: comfort, laughter, and an unspoken understanding of each other’s quirks.
Of course, everyone has naturally fallen into a role. The most fashionable one in our group has the final say on outfits each morning, and it has to pass her standards. Another is our official guide, ensuring we do not waste time getting lost. I am usually the go-to for solo shots, making sure the photos are magazine-worthy, tall and thin included. Then there is the comic relief who keeps us laughing, and the resident enabler, whose greatest joy is ensuring we go home bankrupt but happy. She beams with pride when she is the one who discovers the perfect item for you to buy.
In Copenhagen, another friend has made it her mission to point out the handsome men we pass on the street. And let me tell you, there are plenty. The best part is imagining all the possible scenarios because the Maria Clara in us is still alive. We may giggle, whisper, and admire, but actually walking up to say hello? That is another story.
Sometimes, we even assign love stories to complete strangers, like the tall blond man in the black coat who must surely be a brooding writer, or the guy at the café whom we decided was secretly a prince in disguise. We may be in our 50s, but our imaginations are still as playful as teenagers’.
The ups and downs of traveling together
Traveling with friends, however, is not always as effortless as it sounds. For many, it goes by trial and error. Just because you click at home does not always mean you will survive sharing bathrooms, meals, and tight itineraries.
Some friendships do not make it past the trip. I have heard stories of relationships unraveling after a disastrous vacation. A best friend suddenly becomes an enemy because one hogged the mirror every morning or refused to chip in for taxi fares. One person’s dream itinerary can be another person’s nightmare. And sometimes, the smallest irritations snowball into fights that no one recovers from.
So how do you know if you and your friends are ready for that next level, traveling together? A few things help.
First, match your interests. If one loves hiking while another would rather die than trek a mountain, it is not going to work. Personally, I will happily walk 10,000 to 15,000 steps in a city. But running trails? Not this momma. Common likes and dislikes save you from arguments.
Second, go Dutch. Splitting expenses keeps things fair. No one should be forced to carry someone else’s bill unless it is a planned treat. There is something freeing about paying your own share and not feeling indebted.
Third, pull your weight. If you are in an Airbnb, clean the dishes, cook, do the laundry, and keep your things tidy. In a hotel room, respect each other’s space. Nothing strains friendships more than living with someone who believes the rest of the group is their personal staff.
Fourth, be on time. Nothing ruins a trip more than waiting endlessly for the latecomer who cannot seem to leave the room without applying another layer of lipstick.
And finally, contribute ideas. Do not let one person carry the entire planning load. Research, suggest, and share the responsibility. Even if your suggestion is not chosen, at least you showed that you care about the experience of the group.
Your constant companions
Another secret to traveling well together is humor. A sense of humor can smooth over almost anything. Missed the train? At least you have a funny story. Ordered something strange for dinner? Laugh about it. Ended up lost in a neighborhood no one has heard of? Pretend it is part of the itinerary. When laughter is your constant travel companion, even the mishaps turn into memories you will retell for years.
And then there is the comfort of routine. Younger travelers often push themselves to squeeze every possible activity into one day. But at our age, we have learned that it is okay to slow down. We can spend half a day in a museum and then the other half sitting at a café just people watching. We know our limits, and we respect them. We do not need to climb every tower, conquer every trail, or attend every late-night party.
What we need is connection, laughter, and the simple joy of being together.
Half the joy, half the people you’re with
With my gang, this Vienna, Copenhagen, and Malmo trip proved yet again that we have the right formula. We have tested each other through different cities, cultures, and cuisines, and we are still planning the next.
That is how you know it works. When, instead of vowing “never again,” you find yourself already asking, “So, where to next?”
At this point in life, the destination is just half the joy. The other half is the people you are with. Traveling becomes less about ticking landmarks off a list and more about building moments you can look back on with a smile. And if you find yourself still laughing together on the flight home, still sharing snacks, still sending each other photos weeks later, then you know you have found the ultimate travel companions.
Because in the end, being in your 50s is not just about knowing who you are. It is also about knowing who you want to bring along for the ride.
