Day 1
The tour begins just outside Florence, the capital of Tuscany. Here you will receive your rental bikes and your luggage will be collected before you ride toward the village of Radda in Chianti.
Night 1
We usually book a charming hotel located within the town’s historic walls.
Day 2
Today you ride a circular route through some of the most characteristic landscapes of the Chianti Classico region, with many opportunities to taste local wines, pecorino cheese and seasonal fruit.
Night 2
Return to the same hotel as the first night.
Day 3
Leaving behind the unique scenery of Chianti, the landscape opens up across the Val d’Elsa valley. Soon you will see the famous towers of San Gimignano rising on the horizon.
Night 3
We select a hotel in the historic center of the town with beautiful views over the surrounding countryside.
Day 4
San Gimignano, often called the “Jerusalem of Tuscany,” is not the only highlight of the day. Stunning landscapes accompany you throughout the ride, and you will understand why the ancient Etruscans always chose the most beautiful places for their settlements.
Night 4
Hotel located between the Etruscan and medieval walls of the town, with swimming pool and breathtaking views.
Day 5
The hills characterized by the geothermal steam vents known as soffioni are soon replaced by the Berignone Nature Reserve. Following the old Salt Road, you reach the charming village of Casole d’Elsa, known for its sculptures and artistic details.
Night 5
Our preferred choice is a beautifully restored B&B located in an ancient building on the edge of the village.
Day 6
Today’s stage takes you across the Montagnola Senese hills, offering continuous surprises with historic landmarks along the way. This is a lesser-known corner of Tuscany, making the experience even more special.
Night 6
Your hotel offers not only a large swimming pool but also an excellent dinner not to be missed.
Day 7
Old mines, a canyon reached along the remains of an ancient railway, and the spectacular Brunello vineyards dotted with castles and historic villas are just some of the highlights of today’s ride.
Night 7
You will stay in a hotel with a truly unique view.
Day 8
The Abbey of Sant’Antimo looks as if it has come straight out of a fairy tale, but it is not the only place that will surprise you today. Beautiful landscapes and an ancient fortress that has watched over this area for centuries make the day unforgettable.
Night 8
A charming and welcoming B&B will host you for the night.
Day 9
Today’s climb leads you to the southern edge of Tuscany. The fortress of Radicofani has always been an important border stronghold. The slopes of Monte Amiata bring you into a completely different atmosphere.
Night 9
Another chance to enjoy the thermal waters before returning to the same B&B as the previous evening.
Day 10
A short but intense climb brings you to a historic village that has long been a stop for pilgrims traveling toward Jerusalem. Time seems to stand still here, and there will be many scenic spots where you will want to pause and take in the beauty of the landscape.
Night 10
Tonight you will stay in a small and carefully run hotel.
Day 11
A series of rolling hills leads you through several small villages that remain largely untouched by tourism, where you can wander through narrow streets and charming squares. Today’s stage also brings you to another historic spa town.
Night 11
A small and family-run B&B will welcome you for the evening.
Day 12
Another beautiful abbey and perhaps the most famous cypress-lined road in Tuscany frame today’s ride. You will also pass through vineyards of the Chianti region before arriving in Siena, under the shadow of the Torre del Mangia, where the tour ends.
Night 12
Your final night is spent in a former convent within the city walls, now a comfortable three-star hotel.
Day 13
Departure after breakfast, though you may still have time to explore the hidden corners of this unique city.
