Italy Coast to Coast Cycling Tour
4 Nights – Group of 6+
Italy Coast to Coast Cycling Tour with Sportive Breaks
Is there a better long weekend of riding than this? Embark on an unforgettable adventure from the Adriatic Sea to the Tyrrhenian Sea. Starting in Cattolica, you’ll roll through the rolling hills of Emilia-Romagna and into the heart of Tuscany. Pass through Sansepolcro, a Renaissance gem nestled in the Apennines, before gliding into the medieval splendor of Siena, with its iconic piazza and rich history. The journey concludes in Pisa, where the Leaning Tower greets you at the finish line.
Our Italy Coast to Coast Tour is a 4-night break riding from the sandy beaches of Emilia Romagna to the Tuscan Coast across Italy’s stunning mainland. This group is led by our expert guides and support vehicle as we ride together on the flats and at our own pace on the climbs. Afternoons are spent relaxing with a couple of beers and your pick of the exquisite local cuisine.
We move around each night on our Italy Coast to Coast, so expect no two days to be the same on this beautiful journey across this historic landscape.
Does this sound like your kind of ride? Get in touch to make your dream cycling holiday a reality!
Groups;
This trip is open to groups of 6 or more people. Looking for your next club trip? or maybe a holiday with old friends? Get in touch to start your holiday countdown.
Not your kind of itinerary? Let us know if you want to change the plan and we can adjust it to suit your needs! Let us know how we can make this trip perfect for you.
Spread your payments: Our payment plan is an interest-free payment method where you will have the opportunity to spread payment for your booking
Daily guided rides: Ride leader and support vehicle with mechanic providing regular stops with snacks and drinks
Accommodation: Hotels in Cattolica, Bagno di Romana, Siena and Follonica
Transfers: Airport transfers from Bologna on arrival and back to Pisa. Daily luggage transport
Bike rental: Giant TCR Advanced Ultegra Di2 or similar available for your tour
What's Included?
Accommodation
Stay in 3 or 4* hotels
Fully Supported Riding
Guided group rides
Mechanic Support
Available throughout
Meals
Breakfasts included
Support Vehicle
Support vehicle and luggage transport during the rides
Bike Rental
Bike Rental available
Itinerary
Arrival day – fly into Bologna, transfer to the hotel and warm up ride.
We offer an airport transfer for your group from Bologna Airport, based on your groups arrival time. We suggest aiming to arrive before lunch so you can get riding today.
Our mechanic will help assemble your bikes ready for your afternoon ride. If you rented a bike it will be ready for you upon arrival, the mechanic can help adjust the setup to suit you. We will go for a short spin (1-2 hours maximum) to get the legs going and make sure our bikes are prepared for the riding ahead. Your guide will brief you on the riding ahead and what to expect from your trip across Italy.
~96km distance & ~1,770m elevation
We roll out at 09:30am and head inland towards Sansepolcro. The route takes you across the rolling hills and then into the Appennine mountains. Taking on the Bocca Trabaria which tops out at 1049m above sea level, before finishing on a descent into Sansepolcro.
Today you will start in the region of Emilia – Romagna. Then ride through the regions of Marche and Umbria before finishing in Tuscany.
This evening we stay in Sansepolcro a historical town with a preserved renaissance era centre.
~115km distance & ~1,650m elevation
After breakfast we roll out at 09:30am heading for Siena. Today we will take in some stereotypical Tuscan scenery as we go through the rolling terrain. As we approach Siena you may start to recognise some scenery from Strade Bianche as we will be approaching the finish line, the famous Piazza del Campo. You even have the opportunity to take on one or two white road sections as we approach. After finishing in the historical and instantly recognisable square we will head to the hotel.
~133km distance & ~1150m elevation
Today we finish off with a bang. After breakfast we head for the coast. Firstly we visit the walled, medieval town of San Giminiano to take in the beautiful and historic architecture. We head to the coast of Marina di Pisa to complete your coast to coast, but that’s not all! After pictures at the sea, we then ride back into Pisa to finish at the Leaning Tower of Pisa. A historical end to a trip you wont forget!
We will pack up bikes the night before so you can have a lazy breakfast and still get home to enjoy most of your day.
We offer an airport transfer for your group from Pisa Airport, based on your groups flight time.
Prices and inclusions
Italy Coast to Coast
- From £1169 per person based on sharing a twin room (2 single beds) or double room (1 bed for couple) – based on a group of 14 guests
- £309 Single supplement
What’s included:
- Four nights in three/four star hotels
- Breakfasts included
- One cycling guide on the road
- Van support with snacks & refreshments and mechanical support
- Daily luggage transfers
- Return airport transfers
- GPX files provided
- ABTA protected
Also Available:
- Bike Rental – Giant TCR Advanced Ultegra Di2 or Similar. £269 for the tour
You're in safe hands
We have a team of highly experienced professionals who have been organising cycling trips for over 25 years. We are members of ABTA and ATOL, meaning you can book with confidence
Plenty to choose from
Did you know? We offer the biggest selection of European Gran Fondo and Cyclo-Sportive events.
Spread your payments
Our payment plan is an interest-free payment method where you will have the opportunity to spread payment for your booking. *Selected products. Terms and Conditions apply
Logistics covered
We know the routes, we know the roads. We know how the event works and the best hotels for the start and finish. We organise everything for you; transfers, bike transport, additional feed stops, rep support and more
Find Out More About Other Cycling Hospitality With Sportive Breaks
Etape du Tour de France 2026
France
July 19, 2026
£299
Sportive and Gran Fondo
L’Étape du Tour de France Femmes 2026
France
August 6, 2026
£150
Sportive and Gran Fondo
2026 Giro d’Italia Tours
Italy
May 21, 2026
£3099
Tours and Weekenders