167. The Truth About Traveling with Other People | Luxury Travel Solutions for Groups

Traveling with other people can create some of your best memories, but it can also bring out tensions you never expected. In this episode, I’m sharing the real reason group travel gets complicated and why the destination is rarely the problem. I’ll take you behind the scenes of trips with family, friends, and complete strangers, and reveal what actually determines whether a group comes home closer than ever—or ready to never travel together again.

Waitlist for 2027 Group Trips:
https://makinmemoriestravel.myflodesk.com/setjetting2027

Subscribe to First Class Friday, my new Substack: https://jetsettingwithme.substack.com/

Links Mentioned in this episode:

• 162. 4 Epic Set-Jetting Trips You Can Join in 2027: A Luxury Travel Preview
• 154. How Set Jetting Brings Your Favorite Shows to Life, from A Luxury Traveler's Perspective
  
  

Book a Meeting with Michele here: https://tidycal.com/texasmfs/15-minute-meeting

Connect with Michele on IG: @jetsettingwithmichele or on Facebook: www.facebook.com/groups/MMTinsiders

Contact Michele to plan your next vacation: www.makinmemoriestravel.co/contact

This episode was produced by The Podcast Teacher: www.ThePodcastTeacher.com. 

Transcript

Welcome back to another episode of Jet Setting with Me. It's me, Michele, your friendly wanderlust instigator.

Yes, this episode was originally slated to be about embracing trips to Europe again — but I’m always wont to change my mind. Let’s get into it.  

I want to talk today about something that comes up in my inbox more than almost any other topic. Not which cruise line. Not which hotel. Not even which destination. The question I get asked more than almost anything else — especially from people considering one of my curated group journeys — is some version of this: what if I don't get along with the group?

The question makes complete sense. Traveling with other people is one of those things that sounds wonderful in theory and occasionally becomes complicated in practice. Whether it's a family trip, a friend group, or a trip with people you've never met before, the interpersonal dynamics of group travel are real — and they don't get talked about nearly enough.

One more thing before we get into it — if you are not yet subscribed to First Class Friday, my brand-new Substack, I would love for you to join me there. It publishes every Friday morning, and it is where I go a little deeper: the travel stories, the behind-the-scenes of what I am planning, the books I am reading, and the life in between the trips. It is free to subscribe, and the link is firstclassfriday.substack.com. (of course it is linked for you in the show notes.) 

SECTION ONE: THE QUESTION EVERYONE ASKS

When someone reaches out about one of my set-jetting group trips — the Bridgerton trip, the Emily in Paris trip, the Outlander trip (which, if you don’t already know about the 2027 group set-jetting trips, go back and listen to episode #162) — they almost always want to know two things. Where are we going, and who else is coming. In that order.

The second question is really the first question in disguise. What they're really asking is: will I belong there? Will I like these people? Will they like me? Will I end up at dinner across from someone who talks about themselves for three courses and then goes to bed early while I'm looking for somewhere to dance?

These are fair questions. I asked similar ones the first time I traveled with a group I hadn't chosen myself.

Here is what I have learned from designing and leading group trips: the group is almost never the problem. The expectations are.

When people travel together because they share a genuine passion — a show they love, a story that moved them, a destination they've been dreaming about — that shared foundation does more work than any icebreaker exercise ever could. You already have something. You already have a reason to be in the same room. Everything else builds from there.

My Bridgerton trip to London and Bath proved this to me in a way I genuinely did not anticipate.

Our group had never met in person. They had connected briefly on a welcome Zoom call two weeks before departure — a happy hour where everyone could put a face to a name before we all showed up at Heathrow. We had also matched roommates intentionally, pairing people based on travel style and personality rather than alphabetical order or whoever happened to sign up at the same time.

What I did not fully expect was what happened the moment the last flight landed and the whole group came together for the transfer to Bath. Something clicked. Immediately. Not gradually — immediately. The shared experience of having watched the entire Bridgerton series, of having followed our guest host's content, of having chosen this particular trip for the same reason — it created an instant common language. The van ride to Bath felt like a reunion, not a first meeting.

The night before we departed for home, two of the women I had matched as roommates knocked on my door in their pajamas. They had come to tell me that the roommate pairing had changed something for them. That they had stayed up talking, that they had found in each other something they hadn't expected to find on a group trip with strangers.  Want to hear even more about this amazing trip and how bonded we became as a group?  Episode #154 is for you.  

That moment is why I do this work.

When someone asks me what if I don't get along with the group — my honest answer is: on a well-designed trip built around a shared passion, with people who chose to be there for the same reasons, it almost never happens. When there's friction, it almost never comes from the group. It comes from something else entirely.

SECTION TWO: WHAT GROUP TRAVEL ACTUALLY REVEALS

Here is the thing nobody tells you before you book a group trip: travel doesn't create conflict. It accelerates whatever is already there.

The cousin who is difficult at Thanksgiving is going to be difficult in Amsterdam. The friend who cannot decide at dinner is going to struggle at the restaurant in Prague. The family member who needs to feel heard before they can move forward is going to need that in every city, at every meal, on every excursion — because that is who they are, not a product of the destination.

I say this not as a warning but as a reframe. Because the reverse is equally true. The people who show up for each other at home show up even harder when they're somewhere extraordinary together. The friend who remembers what you ordered last time. The family member who quietly checks that everyone is keeping up. The travel companion who finds the thing that will make you laugh when the afternoon goes sideways. Those people become more themselves on a trip, too.

Group travel is a magnifying glass. It does not create character — it reveals it.

I have been planning a family trip recently. A river cruise, specifically, which is genuinely my wheelhouse. And I will tell you that even as a travel advisor — even as someone who does this professionally, who has been to these cities, who knows the Jewish history and the shopping and the best excursions that no cruise line will ever put in their brochure — navigating the dynamics of planning travel for the people you love most is its own particular complexity.

People who would trust a stranger's expertise without a second thought will sometimes second-guess someone they love, because the relationship adds stakes that a transaction simply does not carry. There is no professional distance. There is only the history between you, the love between you, and the very human desire to get it right for them.

What I have learned from that, and from years of designing group trips professionally, is this: the logistics are almost never the hardest part. The hardest part is the people. And the people are also always the best part.

SECTION THREE: HOW TO ACTUALLY MAKE IT WORK

Whether I am planning a family river cruise or curating a set-jetting journey for eight strangers who share a love of Scottish Highlands and kilts, three things consistently change the dynamic before anyone boards a plane.

The first is establishing one decision-maker early. Not a dictator — a designated tiebreaker. Groups that try to reach full consensus on every decision lose hours and goodwill to choices that genuinely do not matter. Someone has to be the one who says: we're going left. On my curated trips, that person is me. On a family trip, it needs to be someone. Decide before you go.

The second is building in solo time. The best group trips I have ever taken or planned include deliberate windows where people scatter. An afternoon with no scheduled activity, no group commitment, no agenda. You come back to dinner with stories instead of grievances. White space is not wasted time — it is the thing that makes the rest of the time sustainable.

The third is setting the tone before departure. A pre-trip note, an email, a welcome call — something that establishes what this trip is and what it is not. What to expect, what to leave at home, what the shared intention is. On my group journeys, that welcome Zoom call does more work than any printed itinerary. People arrive already knowing each other. They arrive already invested. The trip begins before the trip begins.

CLOSING

Back to the question that started all of this: what if you don't get along with the group?

Here is what I know after years of designing trips for every kind of group: the question almost never becomes the problem. The shared passion does the heavy lifting.

What travel gives you — any travel — is a version of yourself you cannot access from your couch. What group travel adds to that is witnesses. People who were there. Who saw what you saw, felt what you felt, and will remember it alongside you long after you are home.

That cannot be planned. It can only be created through the conditions you set before you ever leave home.

If you are curious about my 2027 curated group journeys, DM me at @jetsettingwithmichele or find the link in the show notes.

If you have a group travel story — a trip that bonded you to strangers, or a family trip that tested you, or a roommate match that surprised you — I genuinely want to hear about your version of the pajama moment. My DMs are always open.

COMING UP NEXT WEEK

Next week — Episode 168 — I am talking about a show I have been waiting for since the moment it was announced. The Little House on the Prairie reboot just dropped on Netflix, and I have thoughts. Set-jetting thoughts. The kind that involves Laura Ingalls, wide-open prairie skies, and a destination that belongs on your travel list for reasons unrelated to covered wagons. That is next week.

Until next time, make every journey a memory worth savoring.