Our Story
Our journey from a small European country to a continent-wide cycling holiday company: the origins, the growth, and what we learned along the way.
This page isn't about what we do or who does it — the About Us page covers that. This is about how we got here. The roads, the mistakes, the decisions that turned a Slovenian day-trip operation into a cycling holiday company covering 20+ European countries.
It didn't happen by design. It happened while testing, riding and refining!
Where It Started
The company that became Cycling Holidays didn't start with cycling at all.
Around 2020, a small team of us launched a few day-trip brands built around showing visitors our home country - Slovenia. Canyoning, hiking, lake visits. Slovenia is a small country with an outsized amount of nature packed into it, and we figured we could show people a side of it the guidebooks missed.
Cycling Was Not The Only Activity
Guests who tried a day ride came back saying it was the highlight of their trip. The roads in Slovenia — particularly through the Julian Alps and over passes like Vršič — are extraordinary on a bike, and we'd been riding them since we were teenagers. We knew where the good descents were, where to stop for coffee, which guesthouses had a terrace worth arriving for. We just hadn't thought of that as a product yet.
The moment everything shifted was a simple one: guests started asking for multi-day tours. Not just a day ride, but a full week on a bike, with hotels and luggage transfer and a route that made sense from start to finish. That was a different kind of problem.
We liked solving it.
The First Riders
The early tours were small. Four or five guests, a route we'd ridden ourselves the week before to double-check the hotels, and a level of personal involvement somewhere between professional and obsessive. We guided the first tours ourselves — literally riding alongside the guests, carrying spare tubes, making restaurant calls from the saddle.
The Trips That Made Us Better
The early tours were not perfect:
A hotel lost a booking on our second-ever departure
A luggage transfer arrived at the wrong hotel
One guest's rental bike had a creak we couldn't diagnose until day three — it was the seatpost
None of it was catastrophic. All of it was the best education we ever had.
Because here is what those moments taught us: the logistics matter more than the scenery. A stunning mountain pass means nothing if your bags aren't at the hotel when you arrive, tired and hungry. Every mistake we made in those early years is now a system, a check, a protocol that runs quietly in the background of every tour we organise today.
The other thing those first tours taught us: not everyone wants a guide riding next to them. They want the freedom to stop when they want, eat where they want, arrive when they feel like it — but they also want someone to have figured out the route, booked the hotels, and moved the bags.
That insight is why self-guided touring became our core format. Not a compromise — the thing our riders actually wanted. We do, however, also cater to those that prefer riding with a guide.
We didn't get here by getting everything right from the start. We got here by caring enough to fix what went wrong — every single time.
Beyond Slovenia
The expansion wasn't strategic in the way a business plan would describe it. It was reactive — driven entirely by the people who'd already ridden with us.
A couple who did Slovenia asked if we could build something similar in Austria. The Danube was the obvious first route — flat, well-signposted, proven demand. We found local partners, rode the route ourselves, tested the hotels, and launched it.
Then someone asked about Italy. Then Croatia. Then Germany.
Each new country meant new roads to ride, new accommodation partners to vet, new logistics to solve — but the model was the same one that had worked in Slovenia. Plan properly, choose hotels carefully, transfer luggage reliably, be available when something goes wrong. Country by country, tour by tour.
The pandemic interrupted everything — and paradoxically, accelerated it. International tours stopped overnight, but day tours in Slovenia boomed. That demand kept the business alive. And the downtime gave us something we'd never had: months to rebuild the product without the pressure of simultaneously running tours.
We rebuilt the GPS systems. Improved the digital guidebooks (which we keep doing on a daily basis). Formalized partner relationships in countries we'd been planning to enter. When borders reopened, we had a better product than we'd had before.
What We Learned Along the Way
5+ years of running cycling holidays teaches you things that aren't in any business book. The lessons that actually shaped how we work:
The best route isn't always the most scenic.
It's the one where the distance between stops feels right, the hotel at the end has a good shower and a terrace with a view, and the road surface doesn't rattle your teeth for the final 10 km. Every route we build is designed around where you sleep, not just what you see.
Luggage transfer is the invisible service that makes everything else possible
Nobody books a cycling holiday because of luggage transfer. But the moment your bags aren't in your room when you arrive — that's when the whole trip breaks. We learned this on tour number two.
E-bikes changed who could ride together, not just who could ride
A couple with different fitness levels used to face a difficult choice: the stronger rider holds back, or the weaker rider suffers. One rider on electric, one on regular, same pace, same experience. It's the single biggest shift in cycling tourism in the last decade — and it's why we offer e-bikes on many tours today.
The best product decisions were made by our riders, not by us
The Danube, Norway, Mallorca — none of them were on a roadmap. All of them were answers to questions guests asked. When someone asks "can you do this?" the answer should always start with yes.
Where We Are Now
Today, Cycling Holidays operates across 20+ European countries with over 160 tours — from flat riverside paths for beginners and families to Alpine road cycling for experienced riders. The team has grown from five people guiding their own tours to a network of travel advisors, route designers, local partners and logistics specialists across the continent.
How About Other Brands and Activities?
The country-specific brands - Slovenia Cycling Holidays, Cycling Holidays Italy and the rest — exist because depth matters more than breadth. Each destination has people who know it at a level a generalist operation can't match. Cycling Holidays brings it all together. The local brands go deeper.
We're part of the World Discovery travel network, which also includes a growing family of active travel brands — all built on the same foundation of quality logistics and genuine care for the people who travel with us.
Explore our other travel options:
What Keeps Us Going
What keeps this going isn't the destinations or the tours — it's the people who keep coming back to them. Every returning rider, every recommendation passed on to a friend, every message that starts with "we want to do another one" — that's what the last 5 years have been built on.
- The Cycling Holidays team
Hassle-Free
We take care of route planning, accommodations, luggage transfers, and all logistics, so you can focus purely on enjoying your ride.
Tried & Tested Adventures
Our cycling routes are hand-picked & tested, to ensure breathtaking landscapes, smooth roads, and maximum safety - giving you the perfect ride every day.
Unbeatable Support
Our 24/7 customer support is where we show our passion, ensuring your cycling holiday runs smoothly and your well-being is always our top priority.
Book with Confidence
We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.
Local Experts
Our professional cycling guides in select locations know the local terrain and are trained to make this once-in-a-lifetime opportunity both safe and enjoyable.
