How hosting group trips for solo travelers became my favorite side hustle

I didn’t set out to start a travel business. I just wanted to see the world—and not do it alone. The first trip wasn’t a product. It was a WhatsApp group chat, a shared Google Sheet, and a half-joke that if we booked the same Airbnb, we could split the cost and pretend we weren’t strangers.

We met in Chiang Mai. Seven of us. One from Singapore. Two from Berlin. One guy who didn’t talk much until the third night. No one wanted to go home. That was the beginning. Not of the brand. Not of the revenue stream. But of the insight: people aren’t just traveling for landscapes anymore. They’re traveling to belong. I didn’t know it then, but that was my first group trip for solo travelers. And it changed everything.

I had always traveled solo—backpacked through Eastern Europe, joined pop-up language exchanges in Mexico City, booked last-minute tuk-tuks in Phnom Penh. I loved the autonomy. The control. The choose-your-own-adventure-ness of it all. But around my late 20s, something shifted. I wasn’t just looking for new places—I was looking for people I could eat dinner with, not just grab food around. And I wasn’t alone in feeling this. I started noticing the quiet signs.

Instagram DMs from old classmates: “You’re always going places—how do you plan it?”
Replies to my stories: “I want to join next time!!”
Comments from hostel bunkmates: “I wish someone else handled the logistics.”

People weren’t saying they were lonely. They were saying they wanted ease, safety, connection—and a reason to stop waiting for their friends to be “available.” That was the emotional gap I didn’t see coming. And once I saw it, I couldn’t unsee it.

At first, it felt weird to take money for it. I wasn’t a travel agent. I didn’t have a license. I wasn’t “qualified.” But I was doing the work. I was researching accommodations, handling bookings, fielding questions about visa rules, creating Google Maps of vegetarian spots, managing the group vibe when people got tired or anxious. I was being the unofficial trip lead.

After the third unofficial trip (Vietnam), I sat down and calculated my costs. Flights, hotels, transport, SIM cards, buffer nights. I realized I was spending hours planning trips that were fun—but exhausting. I didn’t mind. But I also knew: if I was going to keep doing this, it had to sustain me too.

So I made a Google Form. I set a price. I called it a “co-travel experience,” not a tour. I capped it at 10 people. And I told myself: if even 5 book it, that’s my sign. Seven booked. And I made my first profit—$1,300 after all expenses. More importantly, I felt something shift inside: I wasn’t just helping people travel. I was designing belonging.

People think running group trips is about picking the right restaurants or organizing hikes. That’s part of it. But the real magic is invisible.

It’s making the introvert feel seen without making them perform.
It’s defusing tension before it starts by setting tone in the WhatsApp group two weeks before the flight.
It’s choosing accommodations that feel communal without forcing forced bonding.
It’s being the “emotional facilitator” without turning it into therapy.

In some ways, it’s a mix of being a camp counselor, Airbnb host, customer service rep, and quiet leader. You don’t run the trip by barking rules. You set the vibe through trust. I build itineraries with intention: one shared meal a day, one optional “push yourself” activity (e.g. sunrise hike or scooter ride), and always a buffer day for rest.

The structure isn’t to control the group. It’s to protect energy—for them and for me. That’s what people pay for. Not the Google Sheet. The design of the experience.

By the fifth trip, I wasn’t feeling the same buzz.

I was fielding PayPal refund requests from a last-minute cancellation.
I was reading the Airbnb fine print for the third time because someone wanted their own room last minute.
I was staying up past midnight checking everyone’s arrival times.

I loved the community. But I was burning out quietly. Because I didn’t build this like a business—I built it like a friend doing everyone a favor. That’s when I realized: a side hustle that runs on people’s emotions needs real boundaries.

So I made changes.

• I automated trip registration using Typeform + Stripe.
• I created a cancellation policy and made it clear.
• I added a planning fee separate from the accommodation bundle.
• I stopped answering DMs outside office hours.
• I included solo time in the itinerary. For me too.

The results were immediate. Fewer misunderstandings. More respect. And surprisingly—more bookings. People trust you more when you respect your own time.

You’d think most people who book these trips are in their early 20s. They’re not. My average guest is 31. They’re smart, independent, emotionally literate—and tired of waiting for their friends to commit. Some are new to solo travel. Some are done with flaky friends. Some are just… in a life transition and want company without pressure.

And here’s what they don’t want:

• To be treated like clueless tourists
• To be sold an itinerary packed with Instagram stops
• To be forced to do “icebreakers”

They want real connection. Soft community. Flexible plans. Someone to worry about logistics so they can just be. I started using the phrase “intentionally lighthearted” to describe the vibe. Not intense. Not indulgent. Just… designed for adults who’ve done therapy, like good food, and crave a little structure in their chaos.

Is this scalable? Not really. Could I hire trip leads? Maybe—but then I’d be a team manager, not a host. Should I launch an agency? I’ve been asked. But the answer is still no.

What I’ve realized is this: not every good idea has to scale. Some businesses are beautiful because they’re boutique. My sweet spot is 4 trips a year. That’s enough to fund my own travels, grow my email list, and build deep community—without erasing my love for the experience.

And the minute I lose the joy of it, I’ll pause. I’m not afraid to evolve. This is the difference between a hustle and a trap. A hustle funds your life. A trap starts controlling it.

If you’re thinking of hosting group trips, start here:

1. Know your why. Are you doing this to make money, build brand equity, or fund your lifestyle? Your structure depends on that.
2. Design for your energy, not just your audience. If you hate small talk, don’t host meetups. If you love planning but not leading, sell itineraries.
3. Charge like a professional. You can be kind and still value your time. Transparency builds trust.
4. Don’t promise magic. Promise clarity, safety, and light structure. Magic will happen on its own.
5. Be ready to hold space. People bring their real selves on these trips. You don’t need to fix anyone. Just hold space—and set boundaries.

I’m not an influencer. I don’t post reels of drone footage. I don’t have merch. But what I do have is something rare in today’s world: a way to make strangers feel safe enough to be themselves. That’s what I built. And I’m proud of it.

Group trips for solo travelers isn’t a novel concept. But I didn’t need novelty. I needed alignment.

I built this side hustle by following two truths:

1. People crave real connection more than perfect itineraries.
2. The vibe is the product—and the product is trust.

That’s it. No deck. No VC. No 10x. Just one woman, one form, one group of curious humans—and one quiet decision to turn belonging into a business. And that’s more than enough.