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Our 
Story

It Started With... A Trip
 

One chat in Mexico, one idea that wouldn’t quit. (You know, the kind you get after a few glasses of vino.)

 

What if we could bring back the magic of a gap year, but make it work for where we are now? The kind of experience that pushes you out of your comfort zone, introduces you to lifelong friends, and reminds you who you are when you step away from the ordinary.

 

That’s why we created It Started With a Trip.

We are the customer.

We’ve done the solo thing, tried the group tours, and kept hitting the same walls - overpriced trips, exhausting schedules, zero flexibility.

 

So, we built what we were looking for

→ The sweet spot between solo travel and group tours for people like us, who want connection without cliques, structure without rigidity, and experiences without the overwhelm.

→ A gap-year feel, made for grown-ups offering the freedom, fun, and self-discovery of a gap year, but reimagined for people with careers, commitments, and a craving for more.

→  Built around shared mindsets, not just destinations, with groups of like-minded travelers at a similar life stage, creating space for meaningful connection and stories worth telling.

Ready for your own It Started With moments too...? Let's go get it!

Choose Your Travel Vibe 

Solo​​

 It started with me 

No waiting around for someone else to book.

No plus-one required.

Just you, a plane ticket, and a group of solo travellers aged 30-49 who get it and turn into fast friends and the kind of trip that reminds you why you love to travel.

Solo doesn’t mean alone - it means going all in, on your terms.
Duo​

 It started with us 
Travelling with your best mate, partner, or that one (or two) friend who’s always up for an adventure? 
 
You’ve got your built-in travel buddy, but this isn’t just a trip for two. Meet new people aged 30-49, share new experiences, and be part of a group that feels like old friends by the end of it. 

The best trips aren’t just about where you go - it’s who you meet along the way.

Where Will Your Next Adventure Be?

The Middle Ground Thats Been Missing

​Not budget, not luxury - just real travel that hits the perfect middle.

Travel with Meaningful Connections

​It’s not just about the places you go; it’s about the people you meet along the way. That’s why we keep our groups small (max 14)

Your Trip, Your Way

In addition to a full itinerary you'll have the chance to add further bucket list items.

Recharge
and Reset

We get it, some group trips are go, go, go. We believe in the balance between adrenaline and downtime.

Your
It Started With Moment

Everyone travels for their own reason. Whatever brought you here. This is where your it started with moment begins.

Reclaim Your Bucket List

Launching 2026
Save your seat before they all go!
Image by Jaman Asad

CAPE TOWN

Image by kilarov

BALI

Image by Tyler Lastovich

NEW ZEALAND

Image by Polina Rytova

ALBANIA & MONTENEGRO

12 DAYS OF WINE, WILDLIFE & OCEAN VIEWS

8 DAYS OF TEMPLES, TRAILS & ISLAND LIFE

12 DAYS OF WILD PEAKS, GLACIAL LAKES & ADVENTURE

12 DAYS WILD SWIMS, WINDING ROADS & WINE AT GOLDEN HOUR

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