Win! Two spots on a stunning four-day Italian cycling holiday with Sportive Breaks

What's on your cycling bucket list for 2025? How about adding four days of riding through some Italy's most postcard-perfect rolling hills as part of a Sportive Breaks fully supported cycling tour? That's right, we've got two spots on Sportive Breaks' Italy Coast to Coast tour to give away (excluding flights*), meaning our lucky winner and their plus one will be heading off for four memorable days of riding at the start of September, with all the guides, routing, support vehicle assistance, feed stops and logistics taken care of by Sportive Breaks. Our winner's only headache will be deciding who to take!

To enter, simply scroll down this page and fill out the entry form.  Here's everything you get if you are our lucky winner:

A four-night Italian Coast to Coast cycling tour for two people, sharing either a double or twin room from 1st–5th September 2025. This includes all of following: 

- All hotel accommodation 

• On the road cycling guide 
• Mechanical support throughout
• Some meals (breakfast every morning plus two dinners along the way) 
• Support Vehicle, which will also transport your luggage from hotel to hotel. 
• Transfer from Bologna Airport to Tour starting point (hotel in Cattolica) Please note there is only one-time option available, which will be communicated on winning. 
• Transfer from finish (hotel in Follonica) to Pisa Airport. Please note there is only one-time option available, which will be communicated on winning. 
• Bike Rental - Scott Addict or Focus Isacco/Paralane with Ultegra components. 

We need to point out that while just about everything is provided once on the tour, flights are not part of the prize and the winner will need to book their own travel to and from the trip.

Celebrating "the best of this part of Italy", Sportive Breaks has designed a four-day ride from the beach in Cattolica, on the Adriatic, to the Tuscan coast, via the "stunning" rolling hills, gravel roads and sleepy hilltop villages that this part of Italy is famous for. Riding away from the sandy beaches of Emilia-Romagna and towards the climbs of the Nove Colli, the long weekend will traverse the heart of Tuscany before again finishing on the coast "in time to watch the sunset with a glass of Prosecco". We've definitely had worse weekends.

The ride is led by expert guides from Sportive Breaks and backed up by a support vehicle. By the afternoon you'll be able to relax with a couple of beers and whatever local food has been lined up for that day.

Accommodation is a mix of three and four-star hotels, the first night in Cattolica at a family-run four-star hotel with "excellent food". On night two, in the spa town of Bagno di Romagna, there is a wellness area and more top food, the trip passing into Tuscany where you'll stay in Siena before the final evening on the coast in Follonica.

"This small group ride is led by our expert guides and support vehicle as we ride together on the flats and at our own pace on the climbs," Sportive Breaks explains.

On arrival day, there's an airport transfer from Bologna to Cattolica before a spot of lunch while Sportive Breaks' mechanics build bikes. In the afternoon there will be time for a short spin and a welcome dinner.

Day two is when the riding really begins, a 107km (67-mile) day to Bagno di Romagna taking in some of the climbs of the Nove Colli and racking up 2,155m of elevation. In the evening, Sportive Breaks has lined up a night in "officially one of the most beautiful villages in Italy" — with thermal hot springs, access to the hotel spa, and dinner to recover from the day's riding.

> 6 ways to nail your European cycling vacation with Sportive Breaks

There are two choices on day three — a 'short' route of 130km (81 miles) with 1,969m of climbing, or the longer route of 156km (97 miles) with 1,723m of elevation. Whether you pick the shorter but punchier route or longer one with slightly less climbing, both will take in the picturesque Apennines and Tuscan countryside. After a day of rolling hills, vineyards and olive groves, night three is in Siena, where the evening is free to explore.

The final day of riding involves a "stunning" 93km (58 miles) ride through Tuscany via Chianti and through the famous hilltop towns of Volterra and San Gimignano. Then it's on to the Tuscan coast for a beer and celebratory meal. 

The mechanics will pack your bikes that night so you're all ready for the airport, or you could make use of Sportive Breaks' bike rental service and enjoy a Scott Addict or Focus Isacco/Paralene, included with the prize if you'd prefer this. 

Fancy it? All you need to do to be in with a chance of winning the prize is fill out the entry form below, and our randomly selected winner will be contacted within seven days of the closing date to make further arrangements.

Best of luck to all!

* Entries are open to everyone worldwide, but you need to be over 18 years of age. The prize does not include flights to Bologna or return from Pisa to your home destination, and you'll need to make your own way to the start point if you are unable to meet Sportive Breaks at Bologna airport at the required time. At the end of the Tour, you can either be transported to Pisa airport (included) or make your own way from Cattolica. Sportive Breaks can quote you for other transfer times and destinations if the times of the included transfers do not work for your flights (additional costs will apply).