Oscar Boyd is a young British cyclist who has become enamoured of long-distance touring adventures. His photography skills and writing talent have been the basis for four (so far) entertaining and beautifully-produced YouTube videos. They have covered rides the length of Japan, the Westfjords of Iceland and, as we reviewed here, the length of Britain. Now he and his friends have turned their attention to Italy in a glorious new travelogue. The plan was to ride from south to north, beginning in Sicily and ending in the Alps at the top of the Brenner Pass, a journey of nearly 2,000 km and 20 days riding.
The format is similar to Boyd’s previous videos, with nice graphics showing the planned route, and captions indicating where the group stops and points of interest. He is joined at various points by different riders, a motley crew of British, French and Italian friends. His father, who appeared in the British video on his motorcycle, does so again here. These videos are something of a family affair as Alice Boyd, Oscar’s sister, composes the original music in them.
Starting at Mount Etna near Taoromina in Sicily, the journey begins with a ferry crossing to Calabria. While the video is often of Oscar Boyd riding and chatting, he also does a thoughtful voice-over narration. He says that Italian tourism is heavily focused on the north of the country. Looking at the empty roads he rides on at this point, this might be true but if so visitors are missing landscapes of extraordinary beauty.
One of the things that makes these videos so watchable is that the participants are obvious friends and are riding to have a good time. Even riding around 100 kms each day, they take the time to enjoy the scenery, savour local foods, and get a good night’s rest. This is not ultracycling in spite of the overall distance–nobody rides in the dark or sleeps in a ditch.
Moving primarily along the western side of the Italian boot and then towards the centre, the plan divdies the route into three parts of around 500-600 km each. The first is Sicily to Rome, then Rome to Bologna and finally Bologna to the Brenner Pass and the Austrian border. The riders will deal with two mountain ranges: the Appians, the spine running the length of the country, and the Alps. The scenery is extremely diverse. While the roads chosen look to be excellent and lightly-travelled, there are excursions onto gravel, with mixed results.
The riders head into the province of Basilicata and the fascinating city of Matera, considered one of the world’s oldest inhabited settlements. It received global attention as it was featured in the 2021 James Bond film “No Time to Die” and is quite extraordinary. The travellers stay in the old town and visit the network of deeply cut wells and water systems, as well as enjoying the pool in a cave below their hotel.
One theme that appears throughout the video is the riders’ enthusiasm for trying new food. Matera offers up what Oscar Boyd refers to as “one of the most memorable meals of the entire trip.” This is a sandwich known as “the Bullet,” and is made up of a thick ball of burrata (a combination of mozzarella and cream) served with mortadella ham and some brutally hot chili peppers.
The roads go on and the group has a short stop of sightseeing in Gravina, with the beautiful limestone bridge which also appeared in, yes, “No Time to Die.”
Continuing ever northwards, the trends of quiet roads and small towns is broken as the group enters the Eternal City. Rome is given over to a half day for sightseeing and these cycletourists seems to hit all of top places. But soon it is time to ride again and into Lazio.
At this point it is worth remarking on the quality of this video production. As far as one can discern, all the photography is done by Oscar Boyd and his friends, with the impeccable drone work solely by Boyd. Considering how much time is spent by everyone riding each day, along with the opportunities to get lost or strike out on an interesting detour, it is impressive how good everything looks. The truly excellent drone shots cannot be set up instantly and the video work constantly captures striking images, again with excellent editing. Coupled with a fine soundtrack and carefully developed narrative, it is a pleasure to watch throughout. And one of the finest moments is the drone shot of the Villa Farnese in Capraorla, covering the fortress and then the entire town beyond. Beautiful work.
The tour continues onto the familiar roads of Tuscany as the riders face the challenge of the famous White Roads, the Strade Bianche. They reach the wonderful town of Siena and take in a classical music concert in the cathedral, a highlight after a day of hard (and dusty) riding.
Emilia-Romagna is next on the menu and the city of Bologna, home of one of the riders, comes up next. There is some riding up the brutal San Luca climb, which featured in the 2024 Tour de France, and is a regular element of the Giro dell’ Emilia. It passes the Portica de San Luca, with its traditional 666 arches and while Oscar Boyd ruminates on this being a climb too far that day one believes that he will look more kindly on this iconic climb when reflecting on his trip’s highlights. And of course Bologna is particularly famous for its food as well so it’s not all torture.
As the trip continues northwards, the landscape continues to change. There is an interval along Lake Garda, a region that has heavily promoted cycling.
Reaching Trento and the valley beyond the riders sense the change to a more Germanic world as one approaches Austria. Of course, the food is still excellent and the enjoy a very fine paved bikepath that goes for miles along a former railway right-of-way. One of the few days of rain comes as they approach Brixen and the final day of their epic trip, taking them up the climb of the Brenner Pass, sees even more rain.
But no matter if it rains Oscar Boyd and his friends retain their sunny dispositions as they triumph at the top of the pass–even if he describes it as an unromantic place, more shopping mall than summit. But one only needs to think back at all the glorious places that he and his friends experienced. Their trip was just under three weeks but the diversity of landscape, the architecture and, of course, the food is really amazing. Their delight in it all is clear. A great bike trip with some challenges but congenial companions help the miles go by faster. One wishes the video was twice as long. Oscar Boyd concludes with high praise for Il Bel Paese, saying: “Italy is one of the best countries I have ever ridden in and I would gladly do it all again.”
Thanks to his excellent (if rather awkwardly titled) video, we can enjoy it anytime. Having ridden in Sicily, Piemonte, Veneto, Trentino-Alto Adige and Tuscany myself, I too would gladly do it all again. And if you have not cycled in Italy, this video will surely fire up your wanderlust!
“I Tried Cycling the Length of Italy: 2,000 km and 19 Days on the Road–Long Way North Vol. 4”
A film by Oscar Boyd
54 minutes, released August 16, 2026
YouTube Link here.
Oscar Boyd has a Substack account and during the Italian ride posted travel diary entries. He is planning to also provide a how-to for preparing a trip like this, much as he did for the Land’s End-to-John o’Groats one. His Substack account is here.
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