Sportive Breaks

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Italy Coast to Coast Cycling Tour

01 – 05 September 2024

See our flexible bookings payment plans. View Details.


4 nights

Guided Cycling Tour



Italy Coast to Coast Cycling Tour with Sportive Breaks

Is there a better long weekend of riding than this? Starting on the beach in Cattolica on the Adriatic, we ride into the heart of Emilia Romagna taking in some of the climbs of the Nove Colli before heading to Tuscany with some gravel roads, rolling hills and sleepy hilltop villages. We finish on the Tuscan coast in time to watch the sunset with a glass of Prosecco. A perfect long weekend of riding.

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 interior. This small group ride is led by our expert guides & support vehicle. We all ride together on the flats and at our own pace on the climbs. Afternoons are spent relaxing with a couple of beers and some amazing local food.

We move around each night on our Italy Coast to Coast. Starting on the Adriatic coast in Cattolica, our hotel is a family run 4* hotel with excellent food. Moving onto the spa town of Bagno di Romagna our hotel has a great wellness area and even better food. Into Tuscany we stay out in the hills before the last evening on the coast. A mix of 3 & 4* hotels seeing the best of this part of Italy.

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: Scott Addict or Focus Isacco/Paralane with Ultegra components

What's Included?


Stay in 3* and 4* hotels

Fully Supported Riding

Guided group rides

Mechanic Support

Available throughout


Breakfast and 2 dinners included

Support Vehicle

Support vehicle and luggage transport during the rides

Bike Rental

Bike Rental available

Image Gallery


Day To Day

Fly into Bologna & transfer to the hotel

Arrival day. Our airport transfer leaves Bologna Airport at 11.30am getting into Cattolica for 13:00pm. We have time for a spot of lunch while the mechanics build bikes and then a short spin in the afternoon before our welcome dinner.

107km/67m distance & 7,072ft/2,155m elevation

We roll out at 09.30am and head down the coast for a glorious stretch of road that hugs the Adriatic. We then turn inland to take on some of the climbs of the Nove Colli before finishing in the spa town of Bagno di Romagna.

This evening we stay in Bagno di Romagna, officially one of the most beautiful villages in Italy and home to hot thermal springs – perfect for relaxing after a day in the saddle. Enjoy access to the hotel spa and once you’ve recovered, dinner tonight is included.

130km/81m distance (short route) & 6,462ft/1,969m elevation

156km/97m distance (long route) & 5,654ft/1,723m elevation

Today we have a choice of a slightly shorter but punchier route or a longer route with slightly less climbing. We ride out to the South of Bagno di Romagna across the Apennines and soon cross into Tuscany, renowned for its picturesque landscape with rolling hills, vineyards and olive groves. We arrive in the Tuscan gem of Siena – this evening is free for you to explore the delights of the town including the Piazza del Campo where the world-famous Palio takes place twice a year. Dinner is not included this evening.

93km/58m distance & 3,096ft/943m elevation

A stunning ride through Tuscany travelling via Chianti & riding through famous hilltop towns including Volterra & San Gimignano. We finish before sunset on the Tuscan coast for a beer and celebratory meal.

We will pack up bikes the night before so you can have a lazy breakfast and still get home to enjoy the most of your Sunday. We’ll depart the hotel at 09:00am, to arrive at Pisa Airport for 10:00am. Please book flights to depart from Pisa after midday (12:00pm).

Prices and inclusions

Italy Coast to Coast 2024:

  • £799 per person based on sharing a twin room (2 single beds) or double room (1 bed for couple)
  • £1079 per person based on single occupancy of a room

What’s included:

  • 4 nights in 3/4-star hotels
  • Breakfasts and 2 dinners
  • All taxes
  • 1 cycling guide on the road
  • Van support with snacks & refreshments and mechanical support
  • Daily luggage transfers
  • Return airport transfers
  • New water bottle
  • GPX files provided
  • ABTA Protected

Also Available:

  • Bike Rental – Scott Addict or Focus Isacco/Paralane with Ultegra components. £209 for the tour


Sportive Breaks are part of the Destination Sport Experiences Group. When clicking on the booking link below, you will be taken to the Destination Sport Experiences booking engine. If you have any questions, please do contact our team


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 so 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

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