This route offers plenty of flexibility and isn’t limited to the example shown here. There are many different ways to do this journey, and we can adapt it to your requirements. The options are endless, what you’ll find below is simply a typical itinerary.
Day 1 – Warm-up loop
Distance: 39/65km
We fly into Bologna Airport and transfer to Pesaro, where we will start our hotel. Lunch is served upon arrival, before we divide into our guided groups and set out on a warm-up loop to get the legs going!
Day 2 – Pesaro to Bosco
Distance: 136/158km
We ride in a southwesterly direction as we leave the province of Marche and head to Umbria. En route, we pass through the stunning Roman road along the Furlo Gorge, carved out of the rock and following the River Candigliano with sheer rock faces looming above us.
Today is the Giro climb for those who dare. It’s a beautiful climb, rewarding you with views as far as the eye can see!
Day 3 – Bosco to Siena
Distance: 136/155km
Umbria is sometimes known as the younger sister to Tuscany, but today, as we wind our way through remote roads, tiny hamlets and climb to the top of hillside villages, we will find it has a charm and life all of its own. The high mountain road that takes us from Umbria and into Tuscany looks down on Lago Trasimeno in the distance. As we climb ever higher, we come over the hill to the famous medieval village of Cortona, where we enjoy our restaurant lunch overlooking the town square. The reward for climbing all this way is the descent into what will be the setting sun and the stunning views of Siena in the distance, getting ever closer.
Day 4 – Siena to Livorno
Distance: 129/148km
Our last day and we find out the west coast of Italy is very hilly! Our destination is Livorno built several centuries ago with a rich heritage in global trade. It lies nestled on the west side of the Parco Monte Livornese on the edge of the Mediterranean.
As if spending the night in Siena was not enough, our 4th day is the Tuscany from the photos and guidebooks and the reason we are all here. The hilltop villages astound, the medieval towers of San Gimignano reach for the skies, and you can almost taste the Chianti as you cycle past the vineyards.
As the 3 different route options converge on Livorno, we celebrate right on the edge of the Mediterranean on the Terrazza Mascagni, Livorno’s jewel of a Piazza overhanging the sea.
Celebration drinks overlooking the waves before dinner.
Day 5 – Day of leisure!
Enjoy the sights and sounds of Livorno before transferring to Pisa airport and travelling home.
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Sally17/09/2026Trustindex verifies that the original source of the review is Google.
Superb organisation by Team PIEPosted on Google![]()
Sarah Bower16/09/2026Trustindex verifies that the original source of the review is Google.
Four day trip from Ljubljana to Trieste. Lovely friendly staff with excellent efficient organisation. Very nice hotels and great coffee and lunch stops - only wish they could have organised the weather too! Incredible support in tough conditions. Top notch all round.Posted on Google![]()
Jason Bacon16/09/2026Trustindex verifies that the original source of the review is Google.
My 9th PIE organised cycle challenge for the 40tude charity. Another spectacularly organised PIE ride. The way the team and guides handled and responded to all the surprises and challenges thrown their way, making everything smooth for us punters was extraordinary. And very much appreciated. The most professional and friendly group of tour managers, support team and cycle guides. Well done to the whole PIE team and Paul & Tina. You are simply the best.Posted on Google![]()
Greg Martin16/09/2026Trustindex verifies that the original source of the review is Google.
Event team did a great job coping with air traffic meltdown in the UK, storms in Slovenia and road closures from visiting diplomats. accommodating, feeding and moving over 30 people on a daily basis is no easy task and they do it very well! Kudos to Paul and team.Posted on Google![]()
James Purves16/09/2026Trustindex verifies that the original source of the review is Google.
This is probably my 6th rode with pie. They always have things organised and when something isn’t quite right it is fixed quickly and with lots of communication. Paul and the team were brilliant in Slovenia with us all. When you are cycling and out of your comfort zone the last thing you want is to worry about the logistics and pie do that all for you. Thanks And see you soon at the next ride!Posted on Google![]()
Richard Plaistowe05/09/2026Trustindex verifies that the original source of the review is Google.
Pie Events helped me organise the Branditos networking cycles at the International Trademark Association Annual Meeting in London, and sorted routes and guides. Tje rides were thoroughly enjoyable and professionally guided (and 100% safe) Riders from all over the world participated and everyone was effusive in their praise. A fantastic success thanks to Pie Events.Posted on Google![]()
Daniel Osmer27/07/2026Trustindex verifies that the original source of the review is Google.
I've just completed my second 4-day group ride managed by pie. Again, it was a fantastic experience. The 3 person pie team - a trip co-ordinator, ride guide, and on-bike medic - were all top professionals as well as great fun. It was another great trip which the whole team enjoyed. I highly recommend pie.Posted on Google![]()
Ron Rees Davies27/07/2026Trustindex verifies that the original source of the review is Google.
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Michael Taylor24/07/2026Trustindex verifies that the original source of the review is Google.
PIE is outstanding and are indeed passionate about their events. Whether Medical, Portering, Providing Food (paying attention to dietary requirements) and Drink (morning coffee, regular rehydration electrolyte tabs, soft drinks at lunch, alcoholic beverages at the end of the day - if you like that sort of thing), excellent hotels & restaurants, - all needs catered for. Staff - highly sympathetic & empathetic - who convert a steep hill into a mere undulation. All staff were immaculately turned out in identical uniforms. Bike maintenance - Brilliant Route planning - beautiful lanes, B roads, cycle paths - superb routes. Overall - excellent management throughout, with high empathy and support for all participants (including a cat!!).Posted on Google![]()
John Pocock23/07/2026Trustindex verifies that the original source of the review is Google.
Many many thanks for all your team’s support and guidance over the last 4 days. You provided perfect guides and excellent on the spot management. Your ride support team were always on hand to help and kept our water and salt levels up at all times. Your team were really professional and our whole group gelled around them. Of us 8 riders who did the whole 260 mile trip, we have all gone away absolutely delighted with the achievement AND the organisation provided by yourselves.Verified by TrustindexTrustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more