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Tuscany is one of the most famous regions in Italy, boasting culture, wine, breathtaking views and above all, the best road cycling in Europe.
Our cycling tours of Tuscany allow you to fully immerse yourself in the region by allowing you to take in these views, sample the local produce and live like a local for your time with us. Explore our fantastic cycling holidays in Tuscany today to find your perfect adventure.
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.
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Save £100 when you book our tour departing 16 May 2026. Book before 16 February and enter promo code SPRING26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 16/05/2026 Guaranteed | 24/05/2026 | £2,695.00 |
| 12/09/2026 Guaranteed | 20/09/2026 | £2,695.00 |
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 in July and August)
Season 1 – £1795 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep
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.
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Save £100 when you book our tour departing 2 May 2026. Book before 16 February and enter promo code SPRING26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 02/05/2026 Guaranteed | 09/05/2026 | £2,095.00 |
| 31/05/2026 | 07/06/2026 | £2,095.00 |
| 29/08/2026 | 05/09/2026 | £2,095.00 |
| 03/10/2026 Guaranteed | 10/10/2026 | £2,095.00 |
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.
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