Rapolano Terme to Monte San Savino Bike Tour| Book Now

Overview

Explore Tuscany’s white roads, UNESCO valleys, medieval wine towns, and the Chianti hills on this 7-night and 8 day gravel bike tour. Starting in Rapolano Terme, this guided cycling adventure follows iconic Strade Bianche segments, rolls through the stark beauty of Crete Senesi, and finishes in Monte San Savino — one of Tuscany’s oldest hill towns. You’ll pass through renowned wine regions like Montalcino and Chianti, pedal into charming towns like Pienza and Cortona, and unwind at a thermal spa resort each night.

Whether you’re a seasoned cyclist or looking to challenge yourself with something new, this tour is an immersive ride through Tuscany’s most photogenic and legendary cycling terrain.

Day 01 :

Warm-Up Ride around Asciano (~28 km)

Welcome to Tuscany! After meeting in Rapolano Terme and getting set up with your bike, enjoy a warm-up ride around the nearby village of Asciano. It’s a short but scenic loop through rolling countryside to ease into the adventure ahead.

Day 02 :

Ride to Cortona via Val di Chiana (~106 km)

Today’s ride takes you across the fertile plains of the Val di Chiana, a landscape of vineyards, olive groves, and sunflower fields. The highlight is the hilltop town of Cortona, made famous by the book and film Under the Tuscan Sun.

Day 03 :

Into Val d’Orcia and Pienza (~93 km)

Cycle into one of Tuscany’s most breathtaking regions — the UNESCO-listed Val d’Orcia. With its cypress-lined ridges and golden hills, this is Tuscany at its most iconic. Stop in the Renaissance town of Pienza before looping back.

Day 04 :

Crete Senesi Loop or Spa Day (~73 km)

Today is your rest day — with options! Ride a beautiful loop through the dramatic clay hills of Crete Senesi, or relax at the nearby Terme di San Giovanni hot springs, perched on a hill with panoramic countryside views.

5 hours

Day 05 :

Chianti Classico & L’Eroica Roads (~95 km)

Pedal through the heart of Chianti wine country, stopping at the historic Castello di Brolio and Gaiole in Chianti — the start of the L’Eroica vintage cycling race. Visit boutique producers, sample local oils, and enjoy sweeping vineyard views.

Day 06 :

Montalcino & Brunello Wine Region (~91 km)

Ride deep into the famed Brunello di Montalcino wine region. Pass through the Asso Valley, the ancient Monte Oliveto Abbey, and finish in Montalcino — a hilltop town barely changed since the 1500s. Reward yourself with a wine tasting.

Day 07 :

Ride to Monte San Savino (~58 km)

Your final ride is a scenic point-to-point route ending in Monte San Savino. This historic town dates back to the 1100s and offers the perfect finale for your Tuscan adventure. Enjoy the mostly downhill terrain as you roll into town.

Day 08 :

Departure

After breakfast, an optional group shuttle is available to Siena train station for connections to Florence or Rome.