You arrive in the Tuscan countryside, reaching your accommodation in Asciano either by shuttle or on your own. Upon arrival, you attend a tour briefing where the itinerary is explained in detail, and you receive all necessary tour documentation. Your bicycle is carefully fitted to ensure comfort and performance for the journey ahead. If time allows, you can take a warm up ride to the nearby medieval town of Serre di Rapolano, giving you a first taste of the region’s rural landscape and historic atmosphere.

Dinner is included this evening at your accommodation.

The medieval town of Serre di Rapolano is known for its historic stone architecture and proximity to natural thermal springs, which have been used since Roman times.

Meals: Dinner

Accommodation:

• Mid-Range Accommodation: Farmhouse Il Molinello

You begin your ride from Asciano, traveling through the Val d’Orcia, a landscape characterized by rolling hills dotted with cypress trees. The route takes you through the scenic countryside, passing by the village of Montepulciano, which is renowned for its Renaissance architecture and wine production. You continue cycling until you reach Pienza, a town celebrated as an ideal Renaissance city and recognized for its harmonious urban planning.

Breakfast is provided before you set out for the day.

The Val d’Orcia is a UNESCO World Heritage Site, valued for its influence on Renaissance landscape painting and its preservation of traditional agricultural methods.

Meals: Breakfast

Accommodation:

• Mid-Range Accommodation: Hotel Corsignano

You depart from Pienza, cycling through the romantic Renaissance atmosphere as you head toward Montalcino. The route takes you through the scenic Orcia valley, where you encounter the impressive Sant’Antimo Abbey, a Romanesque structure set against the Tuscan hills. Continuing onward, you arrive in the medieval village of Montalcino, renowned as the home of Brunello di Montalcino wine.

Breakfast is included this morning.

Sant’Antimo Abbey is a significant example of Romanesque architecture in Tuscany, dating back to the 12th century and still used by monks for daily prayers.

Meals: Breakfast

Accommodation:

• Mid-Range Accommodation: Hotel dei Capitani

After breakfast, you begin your ride from the vineyards surrounding Montalcino. The route leads you through the rolling terrain of the Crete Senesi, an area known for its distinctive clay hills and open landscapes. You continue cycling until you reach Siena, a city celebrated for its medieval character and well-preserved historic center. Siena offers a lively yet authentic atmosphere, providing a strong sense of Tuscany’s past.

The city of Siena is famous for its annual Palio horse race, held in the Piazza del Campo, and its Gothic architecture that has remained largely unchanged since the Middle Ages.

Meals: Breakfast

Accommodation:

• Mid-Range Accommodation: Hotel Italia Siena

You leave Siena after breakfast, following the ancient Via Francigena route. As you cycle, you pass the medieval walls of Monteriggioni, a fortified village that stands as a testament to Tuscany’s historical defenses. The journey continues through the hills surrounding the Val d’Elsa, offering views of rural landscapes and small villages along the way. Your ride concludes in San Gimignano, known for its striking skyline filled with medieval towers.

San Gimignano is often called the “Manhattan of the Middle Ages” due to its numerous tower houses, which were built by wealthy families as symbols of power and prestige.

Meals: Breakfast

Accommodation:

• Mid-Range Accommodation: Hotel Bel Soggiorno

After breakfast, you depart from San Gimignano, leaving behind its distinctive medieval skyline. The route leads you into the Chianti Classico region, famous for its vineyards and scenic countryside. Today’s ride includes stretches of the historic Eroica dirt roads, which are well known among cycling enthusiasts for their vintage character and challenging terrain. You experience the rural beauty and classic cycling atmosphere that have made the Eroica routes internationally recognized.

The Eroica cycling event, founded in 1997, celebrates vintage cycling and traditional Tuscan landscapes, attracting participants from around the world each year.

Meals: Breakfast

Accommodation:

• Mid-Range Accommodation: Badia a Coltibuono

After breakfast, you cycle through the heart of the Chianti wine region. Along the way, you visit Brolio Castle, a historic landmark where the official method for producing Chianti wine was established in 1872. Continuing your journey, you pass the ancient thermal baths of Rapolano, known for their natural hot springs. The day ends as you arrive in the countryside near Asciano, where you are welcomed by your hosts Elisa and Alessandro. Dinner is included this evening.

Brolio Castle has played a central role in Chianti winemaking history and remains one of the most important wine estates in Tuscany.

Meals: Breakfast, Dinner

Accommodation:

• Mid-Range Accommodation: Farmhouse Il Molinello