Find My Tuscany Bike Tour
From the rolling vineyards of Tuscany and the medieval hill towns to the gentle olive groves and scenic countryside roads, Italy’s Tuscany region offers something unforgettable for every cyclist.
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Looking to plan a bike trip of a lifetime? Browse and filter through our tours or click below to customize your bike tour experience.
Find My Tuscany Bike Tour
From the rolling vineyards of Tuscany and the medieval hill towns to the gentle olive groves and scenic countryside roads, Italy’s Tuscany region offers something unforgettable for every cyclist.
Find My Tuscany Bike Tour
From the rolling vineyards of Tuscany and the medieval hill towns to the gentle olive groves and scenic countryside roads, Italy’s Tuscany region offers something unforgettable for every cyclist.
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Our Tuscany Bike Tours
From Rolling Vineyard Roads to Historic Hilltop Towns
Our custom Tuscany bike tours start in Florence and wind through the beautiful Tuscan countryside. You’ll have the chance to explore charming villages and towns including Siena, as well as:
- San Gimignano – famous for its medieval towers and rich history
- Montepulciano – a picturesque town known for its wine and Renaissance architecture
- Pienza – the “ideal city” of the Renaissance, surrounded by stunning landscapes
- Greve in Chianti – the gateway to the renowned Chianti wine region
- And many more!
Cycle through famed wine regions such as Chianti and Montalcino, enjoying tastings and local delicacies along the way.
Depending on your Tuscany bike tour itinerary, you might challenge yourself on some gentle climbs through the rolling hills or choose more leisurely rides through peaceful vineyards and olive groves.
If you prefer a relaxed pace, you’ll still find plenty to love. Our Tuscany cycling routes are designed to avoid busy roads and highlight the region’s natural beauty and cultural treasures.
Let us plan your perfectly customized bike tour in Tuscany
As with all our private, custom bike tours, we offer options for every type of rider:
- Relaxed routes suitable for e-bikes or hybrid bikes
- More challenging courses for avid cyclists on road bikes
Our suggested Tuscany tour itineraries typically range from 4 to 10 nights, but we’re happy to tailor a tour that fits your pace, interests, and schedule.
Let us curate and customize one of our Tuscany bike tours just for you!
Jamie & Joy's Insider Tips
- Best Time to Ride: The top months for Tuscany bike tours are April, May, June, September, and October—offering mild weather, blooming countryside, and quieter roads ideal for riding.
- Avoid the Summer Heat: If you’re coming from cooler climates, avoid touring in July and August, when temperatures often exceed 95°F (35°C). If you must ride in summer, start early and finish by noon.
- Don’t Miss Iconic Events in Siena: Plan early if you want to experience the Palio di Siena (July 2 & August 16), one of Italy’s most exciting horse races, or the Strade Bianche bike race (early March), which ends dramatically in Siena’s Piazza del Campo.
- Overnight in Hilltop Towns: Stay longer in San Gimignano, Montalcino, Montepulciano, or Cortona—each offers medieval charm, stunning views, and authentic Tuscan hospitality. We can customize your itinerary for deeper immersion in these hidden gems.
- Indulge in Tuscan Cuisine: Savor Bistecca alla Fiorentina, wild mushrooms, truffles (especially in San Miniato), chestnuts, and persimmons in fall. Visit Volterra for its Etruscan culinary influences and artisanal cheeses.
- Wine Tasting Along the Way: In Chianti, enjoy tastings of Chianti Classico wines in villages like Greve and Radda. Further south, Brunello di Montalcino and Vino Nobile di Montepulciano are world-class reds worth savoring. Ask us to include wine tours and tastings in your route.
- Tour Packet with Local Secrets: Every guest receives a detailed custom Tour Packet with curated routes, dining tips, maps, and our favorite artisan stops—so you travel like a local.
