There is one question I get asked surprisingly often: if you could take a group of friends anywhere in the world for a cycling holiday, where would you go?
For years, I never gave people a straight answer. I would tell them it depended on the experience they wanted.
If you love racing and cycling history, there is a strong case for Belgium and the Spring Classics. You can ride the cobbles, watch the world's best riders and spend time in a part of Europe where cycling feels woven into everyday life.
If you want the scale and atmosphere of the biggest annual sporting event in the world, it is hard to go past the Tour de France.
There is a reason Bikestyle Tours operates in all these places. Each offers something different.
Then a good friend and I decided to celebrate milestone birthdays by organising a cycling holiday with a few mates. Suddenly I had to answer my own question.
I got the pen out and started writing down the roads I wanted to ride again, the climbs I wanted to show my friends and the places where I knew we would enjoy ourselves off the bike as much as on it.
The answer became pretty easy.
Italy.
The Stelvio
My favourite climb and one of the great roads of the Giro d'Italia
The Dolomites
Sella Ronda, Passo Giau and some of the best connected mountain riding in Europe
Italian Culture
Coffee, food, cycling history and long evenings around the table after the ride
Ride With Friends
Big mountain days become even better when you share them with your mates
Why Italy?
Italy was my first big overseas cycling holiday, and it left an impression that has never really disappeared.
Before that trip, climbs such as the Stelvio, Gavia and Mortirolo were names I knew from watching professional cycling. Then you ride them yourself and they become something completely different.
You remember the sound of freewheels on the descent, the changing temperature as you climb higher, the snow beside the road, the coffee stops, the arguments about who attacked whom and, eventually, sitting around a table over dinner talking about the day.
For me, Italy gets that combination right. The riding can be enormous, but the holiday never becomes only about the bike.
View Our Epic French & Italian Alps TourItaly For Cyclists At A Glance
Best For: Climbers, cycling groups, clubs and riders who enjoy big days followed by good food and relaxed evenings.
Iconic Climbs: Stelvio, Gavia, Mortirolo, Passo Giau, Sella Ronda, Monte Grappa and Madonna del Ghisallo.
Why We Keep Returning: The variety. You can ride high Alpine passes, the Dolomites, Lake Como and roads steeped in Giro d'Italia history without ever feeling like every day is the same.
The Bikestyle Connection: Many of these roads feature across our Giro d'Italia and Epic French & Italian Alps cycling tours.
Explore Bikestyle Cycling Tours
Putting My Money Where My Mouth Was
Planning a trip for paying guests is one thing. Planning a cycling holiday for your own friends is another.
There was nowhere to hide. These were mates who knew I had spent years riding and guiding throughout Europe, so expectations were reasonably high.
I started with a simple question: which rides would I genuinely want to do again?
Not the roads I thought looked good in a brochure. Not climbs chosen because everyone had heard of them. I wanted the roads that had stayed with me after years of riding in Europe.
Very quickly the page filled with Italian names.
Stelvio. Gavia. Mortirolo. Sella Ronda. Ghisallo. Monte Grappa.
By the time I had finished planning, I realised I had effectively designed something very close to one of our own Bikestyle Tours itineraries.
What I learned: A great cycling holiday is not about squeezing every famous climb into the itinerary. The best trips have a rhythm, hard days, easier days, good accommodation, sensible transfers and enough time to actually enjoy where you are.
The Stelvio, The Climb I Would Ride Again Tomorrow
If there is one climb that explains why I keep choosing Italy, it is the Passo dello Stelvio.
The summit sits at around 2,758 metres in the Rhaetian Alps. The famous ascent from Prato allo Stelvio is approximately 25 kilometres long, climbs around 1,850 metres and includes 48 numbered hairpin bends.
Those are the statistics. They don't really explain the ride.
What stays with me is climbing high above the valley with snow-covered peaks around you and watching those famous switchbacks stack up against the mountain.
Late May can be particularly memorable. There can still be huge banks of snow beside the road, which makes the whole place feel even more dramatic.
It is a serious climb, but it is also the sort of road where you settle into your own pace. Some friends ride ahead, some stop for photos, others just keep turning the pedals. Eventually everyone ends up together at the top.
That is one of my favourite parts of riding mountains with friends. You do not need to climb every kilometre side by side to share the experience.
Passo Dello Stelvio At A Glance
Summit: Approximately 2,758 metres
Prato allo Stelvio Ascent: Approximately 25 kilometres
Elevation Gain: Approximately 1,850 metres
Famous Hairpins: 48 on the Prato allo Stelvio side
Giro History: The Stelvio first appeared in the Giro d'Italia in 1953, when Fausto Coppi attacked on the climb during one of the defining moments of his career.
For cyclists, the Stelvio is one of those rare roads that lives up to the reputation. You see photos of the switchbacks for years, but standing on the pedals yourself with the road curling below you is completely different.
Planning to ride it? View the full Passo dello Stelvio elevation profile, gradients and climb details on Climbfinder .
Ride The Stelvio With Bikestyle Tours
Why The Stelvio Means So Much To Me
The Stelvio was one of the first genuinely famous European climbs I rode, and it is still my favourite.
Part of that is probably sentimental. Your first big overseas cycling holiday sticks with you.
But I have also returned after riding plenty of other famous roads, and the Stelvio still delivers.
The scale of it, the history, the switchbacks and the feeling of being properly high in the Alps all combine into one memorable day on the bike.
When friends ask me which climb I would happily go back and ride again, I don't need much time to think about the answer.
The Stelvio.
Then There Are The Dolomites
If the Stelvio is my favourite individual climb, the Dolomites are hard to beat for an entire day on the bike.
The Sella Ronda is a perfect example.
Passo Campolongo, Passo Gardena, Passo Sella and Passo Pordoi link together into a loop that seems almost designed for cyclists.
You climb, descend, regroup, grab a coffee and then do it all again with a completely different mountain backdrop.
For a group of friends, this type of riding works particularly well because there are natural places to regroup and nobody needs to ride at exactly the same pace.
There is always some friendly competition, of course. Put a group of cyclists at the bottom of a mountain and somebody will eventually decide that the next five kilometres are suddenly very important.
The Problem Is Deciding What To Leave Out
Once you start planning a cycling holiday in northern Italy, the list of possible rides gets out of hand fairly quickly.
The Gavia has that big mountain feel and plenty of Giro history.
The Mortirolo is completely different, narrower, steeper and much less interested in making your life easy.
Monte Grappa offers several approaches and another strong connection with Italian cycling history.
Near Lake Como you have the Madonna del Ghisallo, where the climb leads you to one of cycling's most important spiritual and cultural landmarks.
Then there are all the roads between those famous names. They are often where some of the best riding happens.
Our Experience
The interesting thing about this trip was that I travelled on a Bikestyle Tours departure as a guest rather than as the owner standing on the other side of the operation.
I was there with friends, celebrating a milestone birthday and simply enjoying the experience.
It reminded me why we structure our trips the way we do.
When the transfers, accommodation, bike support and routes are taken care of, you stop thinking about logistics and start concentrating on the important stuff, the next climb, the coffee stop and whatever story is going to be exaggerated over dinner that night.
Then The Giro Became Part Of The Story
I wasn't actually planning the birthday trip around seeing a bike race.
The idea was simple, get a few friends together and ride the roads I loved.
But when you start linking together the Italian Alps, the Dolomites and famous climbs from cycling history, you inevitably find yourself in Giro country.
By the time I had finished planning, our route looked remarkably similar to parts of our Giro d'Italia tour.
Seeing the race became a bonus rather than the reason for going.
There is something pretty special about riding a mountain yourself, knowing exactly what it feels like, and then watching the professionals race over roads like it a few days later.
Explore Our Giro d'Italia ToursTips For Planning A Cycling Holiday With Friends
Don't Make Every Day Epic
It is very easy to open a map of the Alps and start adding famous climbs. Be careful. Three enormous mountain days in a row can quickly turn a holiday into a training camp.
Plan For Different Riding Speeds
Friends rarely climb at exactly the same pace. Pick sensible regrouping points and routes where riders can shorten or extend the day if needed.
Leave Time For Coffee
This sounds obvious until someone creates an itinerary timed to the minute. Some of the best parts of riding in Italy happen when nobody is in a rush.
Think About The Logistics
Moving riders, bikes and luggage through the Alps takes planning. Transfers that look short on a map can take considerably longer on mountain roads.
Use The Support Vehicle
There is no prize for making every rider complete every kilometre. A good support vehicle gives riders options and can turn a difficult day into a great one.
Remember You Are On Holiday
The bike is the reason you came, but it shouldn't be the only thing you remember. Enjoy dinner, stop for the espresso and spend some time experiencing Italy away from the saddle.
Why Italy Works So Well With Friends
Some of my favourite memories from cycling trips have very little to do with power numbers, gradients or average speed.
They are usually from afterwards.
A coffee that turned into a long stop. A beer at the hotel. Dinner where everyone retells the same moment from the ride from a slightly different perspective.
Italy suits that type of cycling holiday.
You can ride seriously hard during the day without feeling like the rest of the trip needs to revolve around training and recovery.
The riding gives the day structure. The friendships, food and conversation are what fill everything around it.
My advice: When planning a cycling holiday with friends, don't start by asking how many famous climbs you can fit into ten days. Start by asking what sort of memories you want everyone talking about when you get home.
Would I Choose Italy Again?
Absolutely.
I still love Belgium during the Spring Classics. I still think every cycling fan should experience the Tour de France. France has some of the greatest mountain roads in our sport.
But if you handed me a group of friends, our bikes and enough time to go somewhere simply because I wanted to ride there, I would choose Italy.
I would ride the Stelvio again.
I would take them through the Dolomites and around the Sella Ronda.
We would ride hard enough to earn dinner, but not so hard that we forgot we were on holiday.
And somewhere halfway up a climb, one of the group would inevitably ask where we were riding tomorrow.
After years of avoiding the question, I think that is probably the best answer I can give when someone asks me where my favourite place to ride is.
Ride The French & Italian Alps In 2027
Join Bikestyle Tours for 10 days across the French and Italian Alps, including Alpe d'Huez, the Galibier, Bernina Pass and my personal favourite, the Passo dello Stelvio.
Frequently Asked Questions
For mountain cycling, the Italian Alps and Dolomites offer an exceptional concentration of famous climbs, including the Stelvio, Gavia, Mortirolo, Passo Giau and the passes of the Sella Ronda.
Yes, provided you have prepared for sustained climbing. The altitude and length make it a serious ride, so pacing, appropriate gearing and mountain weather need to be considered.
For a first Italian cycling holiday, combining the Italian Alps and Dolomites gives a group access to famous climbs, varied riding, Italian cycling culture and plenty to enjoy away from the bike.
Generally, summer provides the most reliable access to the high mountain passes. Conditions vary from year to year and snow can affect the higher roads outside the main summer period.
Yes. We can create a bespoke cycling tour around your group’s riding ability, preferred destinations, dates and the type of experience you want. Whether it’s tackling the Italian Alps with friends, following a Grand Tour or planning a club trip through Europe, our team can build the riding, accommodation, transfers and support around your group. Learn more about Bikestyle Tours Bespoke Cycling Tours.
Instagram
Facebook
YouTube
LinkedIn
