.png){kind=logo}
Tuscany holds the famous city of Florence, one of Italy’s most beautiful icons, however there is more to Tuscany than just Florence. Tuscany is also home to the Apennine Mountains, famous towns of Siena and San Gimignano and Chianti’s olive groves and vineyards, all of which are perfect for exploring on a leisure cycling holiday.
Explore our range of leisure tours below to find the tour that suits you and your cycling needs today.
Tuscany is a world-famous cycling destination, iconic within cycling history, and certain regions stand out for their scenery, routes, and accessibility for different types of riders.
Val d’Orcia – Famous for rolling hills, cypress-lined roads, and picturesque villages, Val d’Orcia is ideal for those seeking leisurely cycling experiences in Tuscany or gentle road rides. Its smooth roads and picturesque landscapes make it perfect for beginners and riders looking for scenic, relaxed days in the saddle.
Chianti Classico – Vineyards, olive groves, and winding country roads define this region. Chianti offers more undulating terrain, making it ideal for confident road cyclists and those seeking a mix of challenge and scenery. Cyclists can stop at local wineries and trattorias, making it a perfect blend of cycling and culture. You’ll see all of this in our Classic Tuscany holiday.
Tuscany Trail – For adventurous riders seeking longer distances and mixed-surface routes, the Tuscany Trail combines road cycling and gravel adventures across the region. It’s ideal for experienced cyclists and those looking to explore beyond the main towns, with rewarding landscapes and varied terrain.
Whether you’re seeking relaxed cycling holidays in Tuscany, scenic road rides, or a multi-day challenge, these destinations showcase why Tuscany is among the world’s most beloved cycling regions.
This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/05/2026 | 13/05/2026 | £1,495.00 |
| 25/09/2026 | 02/10/2026 | £1,495.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1695 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1995 15-30 Jun and 01-08 Sep
Alternatively for a great value holiday, please select one of our scheduled departures below.
To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1295 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1495 15 – 30 Jun and 01 – 08 Sep
Alternatively for a great value holiday select one of our scheduled departures below.
To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.
This holiday has been designed as an e-bike tour allowing you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 23/05/2026 Guaranteed | 30/05/2026 | £2,395.00 |
| 12/09/2026 | 19/09/2026 | £2,395.00 |
Get in touch and we'll help you find your perfect trip.
Tuscany offers far more than scenic roads — it’s a playground for diverse cycling experiences that suit all tastes and abilities. One standout way to cycle Tuscany is on gravel, where you’ll leave the busy roads behind and explore quiet farm tracks, rolling country lanes, and historic paths that wind through vineyards and olive groves. Skedaddle’s gravel-focused Tuscany cycling holidays bring these routes to life, giving you a true sense of the region’s rich landscape and rural charm.
Another increasingly popular option is e-bike touring. Perfect for riders who want to enjoy the scenery with a little extra support, e-bikes let you tackle longer distances and rolling terrain with ease. Glide through Val d’Orcia’s iconic hills, explore the peaceful lanes of Chianti Classico, or take in panoramic views without strain.
For traditional road riders, there are also cycle tour options in Tuscany that combine gentle climbs with cultural stops, local food tastings, and leisurely progress through historic towns.
Whether you’re seeking adventure on gravel, effortless days on an e-bike, a challenging mountain climb, or classic road touring, Tuscany cycling holidays offer unforgettable experiences for every style of rider.
Tuscany’s roads are generally quiet and well-maintained, with smooth asphalt on main routes and peaceful, scenic country lanes. The famous ‘white roads’, the Strade Bianche, offer a more rustic gravel experience which is legendary within the world of professional cycling. The rolling Tuscan hills offer rewarding riding for regular cyclists, with quiet paved roads, undulating terrain, and the option to explore off-road gravel paths through vineyards and olive groves.
Tuscany enjoys a mild Mediterranean climate. Spring and early autumn offer ideal cycling conditions, with warm days and cool mornings. Summers can be hot, especially inland, while winter is cooler but manageable. These conditions make Tuscany cycling holidays enjoyable almost year-round, particularly for cyclists who enjoy active days, rolling landscapes, and the reward of exploring by bike.
Cycling in Tuscany is as much about the culture as the scenery. Riders pass through medieval towns, historic villas, and bustling piazzas, with chances to sample local wines, olive oils, and regional cuisine. It’s a richly rewarding way to experience Tuscany’s history and atmosphere for cyclists comfortable with rolling terrain.
An interview with Lieven about what makes Veneto such a great gravel destination
Do you love to indulge in local delicacies? Read about this Italian gem...
