Tuscany Ride Packages

Siena and the rolling hills of Tuscany offer an unforgettable blend of world-class cycling, rich culinary traditions, and breathtaking scenery. Ride through cypress-lined roads, medieval villages, and historic vineyards, where every turn reveals postcard-perfect views. After a ride, indulge in local Chianti & Montalcino wines, handmade pasta, and rustic Tuscan fare. Whether you're challenging yourself on Strade Bianche routes or simply savouring slow travel, Siena and Tuscany deliver a perfect mix of adventure, culture, and indulgence.

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Time your visit for key events including the Palio, Strade Bianche or Eroica for even more incredible moments. Off the bike we can arrange a host of fantastic experiences including a family owned cooking school overlooking the vineyards of Montalcino, private winery visits, guided walks in the Val d'Orcia region, tours of the towns, unique dining experiences and more.

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Base tour packages include:

Four nights' accommodation with breakfast at our partner hotel, La Villa di STR

3 days' premium road or gravel bike rental

Bike delivery & collection

Over 1,400km in mapped ride routes to choose from + GPX files

Dining and cafe recommendations, and more

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Rider packages from 880 Euro based on twin share

Non-rider packages from 600 Euro twin share

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Extensions to your stay, hotel upgrades, e-bikes, guided rides, transfers & other activities can be added to your experience.