Pisa-Rome Cycle Challenge
300 Miles / 4 Days
Dates:22-27 Sept 2026
To join our Italian Fundraising Adventure, you’ll need to arrive in Pisa by Tuesday 22nd Sept. Our hotel is conveniently close to the airport and we will be on hand to collect your bikes. You can look forward to 4 days of challenging cycling through Italy’s most stunning scenery 23-26 Sept. Depart Sunday 27th Sept.
The Route
You’ll be earning your sponsorship:-
Cycling 300miles/20,000ft, 475km/6,100m.
These are the minimum metrics – did we mention you need to train?
For the fittest riders there are daily optional Breakaway sections to test yourself up the hairpins of adjacent hill top towns or chain gang round some of the huge lakes before re-joining the main peloton (see below).
Day 1: [73miles/116km, 4,350ft/1,326]
Starting beneath the Unesco World Heritage Site (#) Leaning Tower of Pisa, we warm up with some easy cycling across the flatlands of Valdera until the road steepens for our first climb into the hills of Tuscany. The sight of the medieval hill-top San Gimignano(#) hoving into view, sets the scenic standard for our journey as we undulate to our night stop in the stunning Siena(#) – our 3rd Unesco site of the day! – for a well deserved glass of the local Chianti and pasta at the Trattoria Fonte Giusta.
Day 2: [78 miles/125km, 5,860ft/1,326m]
South further through the Val O’Orcia(#) region and the breath-taking Crete Senesi Tuscan landscape of durum wheat fields, vineyards, isolated farmhouses and cypress lined avenues. The exquisite ancient towns of Pienza and Montepulciano, are the locations for lunch and our afternoon picnic, as we sample the local Pecorino Cheese and the eponymous wine, before we arrive at one of the regions’ famed Spa towns, Chianciano Therme, for pasta and (more) wine.
Day 3: [78miles/6,115ft, 125km/1,864m]
We dive further down the valley of Val O’Orcia, and then up and down again (it’s the hilliest day) as we leave the Tuscan landscape and encounter the first of Lazio’s massive, majestic lakes formed by the craters of collapsed volcanos. Lunch is served on the shore of Lake Bolsena before we skirt the 25km around its western edge and climb again to the walled town of Montefiascone for gelato or cold beers. A 12km descent sets you up for the final push to San Martino al Cimino where you can replenish your spent calories at our Pizza Party.
Day 4: [71miles/3,688ft, 114km/1,123m]
Our shortest and easiest day (it’s virtually all downhill!) will continue to take your breath away as we visit Lake Vico for coffee, Lake Bracciano for lunch before bisecting the Veio Regional Park to reach the outskirts of Rome. Here we join the car-free Tiberina Cycle Path as it traces the River Tiber 15km into the centre of The Eternal City. Emerging just 2km from the Vatican City, our tightly formed full Peloton sweeps to St Peter’s Square for a brief spiritual photo opportunity before pressing on to our Gladiatorial finish at the Colosseum for the money shot.
Rome Party
At our boutique Hotel in the lively Trastevere area, a Prosecco Reception awaits you as you swap hilly road stories about your incredible fundraising adventure and get you primed for our Party featuring live music. The hard core can continue out into Trastevere where more bars await.
What’s included
What’s not included
Minimum Sponsorship Requirement:
We ask that you raise a minimum of £2,000 Sponsorship to support YLvC. You will be undertaking a massive physical challenge and your event fee pays all the costs of your own trip. Every penny of sponsorship raised will be going directly to YLvC and their experienced fundraising team will offer help and advice should you need it.
YLvC Mission:
YLvC Mission: When a child or young person is diagnosed with cancer, their whole world can feel like it’s falling apart. Independence is taken and confidence is stolen. Stability no longer exists. The future suddenly feels uncertain. The impact of cancer on young lives is more than medical. And that impact can be felt by entire family. That’s why Young Lives vs Cancer exists.
Their specialist social workers help children and young people with cancer and their families navigate the emotional and practical impact of cancer. They remove barriers, solve problems and prioritise wellbeing. And they stop at nothing to make their voices heard and their unique needs understood, so they can get the right care and support at the right time.
Your sponsorship of £2,000 could enable four families to stay together for a week at one of Young Lives vs Cancer’s Homes from Home. More than a place to stay, they’re somewhere families can enjoy home comforts like home-cooked meals and fresh pyjamas. They’re a safe, supportive space where families can relax away from the hospital.
Or it could fund 78 hours of support from a Young Lives vs Cancer specialist social worker so that children, young people and their families always have someone by their side throughout their cancer journey.
Fitness & Training:
You will need a good level of fitness, and ideally, specific road bike experience or training, to complete this event, traversing the beautiful but hilly Tuscan landscape. The group will divide into smaller Pelotons of different speed groups (typically averaging 12-15mph, 15-17mph, 17mph+) and you can move between the groups at each stop, whenever the mood takes you.
Non or Irregular Cyclists:
Assuming you have a base level of fitness, playing/doing regular sport, you will be able to acquire the required cycle specific fitness and cycling skills, following a training programme in the months leading up to the event. We can help with the programme and offer tailored advice, plus there will be ad-hoc road cycle meet-ups to get you used to both the road and riding in groups.
Regular Cyclists:
Will need to train too. 300 miles over hilly terrain in 4 days is more than even most club cyclists are used to. For those who have completed a London-Paris, the distance is about the same, but you’ll need just a bit more in the tank to be able to enjoy the hills.
The Hills:
The route is hilly, for all but the first and last 30 miles – not many flat bits. This means you need to be able to cycle up hills (in case you were in any doubt) but on the plus side, you get to rest as you coast down many beautiful descents. And remember these are Tuscan hills, not Alps or even brutal UK moorland climbs. Italian road builders are actually much more forgiving when it comes to gradients, than in the UK.
Strava Junkies’ Breakaways:
We know you like to be tested so we’ve thought of that. Every day there will be optional Breakaway sections to take on the hairpins up to, and down from, the hill-top towns dotted along the main route, or to chain-gang round the whole of one of the massive lakes, before rejoining the group for food stops. We want you to be as excited, and exhausted, as the rest of the Peloton.
Flights:
Flights are not included in your Event Fee. There are multiple options to get to Pisa and to depart Rome. You need to make sure you are in Pisa by Tuesday 22nd September 2026 (many choose to arrive earlier to take in the sights) and the Event ends late Saturday night 26th September, so the majority depart Sunday, but again a tour of the Colosseum might delay you.
Bikes:
We’ve found most people are happy to book their bike on their flight (in a suitable bike box). BA’s Economy Plus ticket allows you to use your 23kg luggage allowance for your bike box, with your lycra and party frock easily fitting inside your hand luggage. Easyjet charge about £50 each way for a bike box. Bike boxes can be hired for about £50 for a week. Your local bike shop will always help you to pack a box and our mechanics will be on hand to help reassemble/repack in Italy. If you’d really rather have your bike transported by a specialist company, we can put you in touch.
FAQs
Where your sponsorship goes
See YLvC Mission section or visit Young Lives vs Cancer website.
What are the speed groups?
The number and speed of the different pelotons will depend upon the final make-up of the group, but typically averaging 12-15mph, 15-17mph, 17mph+. You will be able to move between groups each day or during lunch/drinks stops as the mood takes you.
What if I’m a solo rider?
The camaraderie on these events is always remarkable, bonded by the cause and the magnitude of the challenge. You will fit right in.
What do I need to take?
We encourage you to pack light. Cycle clothes, compulsory helmet, casual clothes for the evenings and a change for Saturday’s Party is about all you need – hand baggage is sufficient. You’ll get a more detailed list before the event.
What happens to my luggage?
Your luggage will be transported by GTC between our hotels and be ready for you when you check in. The check in process is also handled by GTC who will hand you your key on arrival. Drawstring Day Bags will be allocated for any small items (sunscreen, medicines, phone chargers etc) and you will have access to them during the day
Will I be sharing a room?
Hotel accommodation is on a twin share basis. You may request to share with someone on your Booking Registration or state if you would be prepared to share with someone of the same sex. Alternatively, you can pay a single supplement.
What if my bike needs repair?
You need to be carrying the tyre levers, inner-tubes and pump to be able to fix a puncture on the road but, for anything more complicated, our mechanics will sweeping behind the Pelotons to fix you up and keep you on the move. Parts or local shop repairs will be chargeable.
Do I have to ride a road bike?
This is a tarmac road event so a road bike is perfect. However, you could choose to use an MTB or flat bar bike as long as you were confident it had the correct gearing. *We are also happy to discuss the gearing on your current bike (road or otherwise or to advise if you are thinking of purchasing a bike.
Can I hire a bike for the event?
The point to point route makes this a tricky option but we can discuss, if required.
What are the Cancellation Terms?
The £300 deposit is non-refundable. See our Booking Conditions for further cancellation details.
Are my payments protected?
Grand Tour Cycling Ltd is member of ABTOT (no. 5668) which provides financial protection under the Package Travel and Linked Travel Arrangements Regulations 2018 (Booking Conditions)
Fundraising:
YLvC will collecting sponsorship directly through their dedicated Justgiving page.
Can we raise funds as a team? Yes, we encourage team fundraising for family and friend groups or corporate teams. There is an option to create or join a team on Justgiving.
When do I have to complete my fundraising? We request that all sponsorship is sent to YLvC by 20 December 2026, at the latest.
If your question has not been answered here, email Grand Tour Cycling at info@grandtourcycling or call 07977 557734.
