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Treasures of Tuscany Renaissance glory days, art + frescoes, medieval fortresses, mosaics, museums, vineyards, romanesque jewel

There is still time to book your bike trip in Tuscany. Experience the true essence of medieval Tuscany, where history and beauty fill the heart.

Spin through rolling vineyards, savor pecorino cheese, homemade pasta pici, fruity olive oils and sip local Brunello and Nobile wines. Read  more >

Short Escape Tuscany Wine Tour

Short Escape Tuscany Wine Tour, a luxury, self guided bike tour


Our Beautiful Tuscany Wine Country Bike Tour offers a sunny Mediterranean ambiance and a spirited flair for hospitality. Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life!

Self Guided Tour, 5 Days/ 4 Nights

Explore Tuscany Wine Country on this short escape. This is a shorter (5 day/4 night) version on our most popular Tuscany Biking trip – offering 3 full days of cycling and 2 half days. So saddle up for a great trip in Tuscan Wine Country…
Tour Departures: Any date between 15th March to end of October

Pienza ~ Montalcino ~ Chianti

Definitely our best selling bike tour in Italy, this memorable cycling tour lets you experience the region’s world famous wine culture. Bike along tranquil country lanes, tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys and medieval forts. Staying in Pienza, Montalcino, Siena and heart of Chianti, you are sure to experience the true essence of Tuscany, where history, beauty and, of course, wine abound.

Day 1: Pienza
Meet & Greet in Pienza, widely known as the “ideal city of the Renaissance”  for your welcome, orientation and bike fitting. Pienza exemplifies Take a stroll through the beautiful cobblestone streets ~ the town streets are full of small charming shops selling typical local products, such as fine wines, pecorino, spices, pici (handmade pasta) and so on. We recommend stopping and tasting! Optional test ride to San Quirico d’Orcia.   Distance 20km /12.5 miles.

Day 2: Montepulciano & Vino Nobile
Today’s bike ride takes you on a looped ride to Castelmuzio, Montichiello and Montepulciano ~ the jewel of Southern Tuscany.  Stop along the way to visit the convent where parts of The English Patient were filmed, and in the enchanting hamlet of Castelmuzio. Arrive in Montepulciano for lunch before returning to Pienza with a stop in the village of Monticchiello. Distance 55km/34 miles.

Day 3: Montalcino Brunello Country
Ride from Pienza to Montalcino, with a pause in the fairy-tale like Bagno Vignoni, a miniature spa town. Lunch in Castiglione d’Orcia, then push on to the monastery of Sant’Antimo before heading on to your destination Montalcino, a town renowned for its wine. Visit the 14th century fortress to see a breathtaking view of the entire valley you’ve just biked. Distance 46 km/ 28,5 miles

Day 4: Siena
Today you start your bike ride with a 10 km descent and pass through Buonconvento, heading northbound to Siena. In Murlo visit a fascinating Etruscan Museum. Continue to Ville di Corsano, end up at the arch gate San Marco. You’ll have time to take a leisurely stroll around this art city and explore the wonderful Torre del Mangia, Duomo and Piazza del Campo. Option A: 60 km/37.5miles – Option B: 52 km/31 miles

Day 4: Chianti Hills
End of bike tour – optional bike ride in chianti to Castello di Brolio, a beautiful bike ride on Chiantigiana road. Distance 50 km /31 miles

What’s Included?

Four nights in excellent three-star superior hotels
Four breakfasts
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions in handbook
All Baggage transfers
Pick-up of bikes and gear in Siena
Sales taxes

Tour Departures: Any date between 15th March to end of October

Palazzo Squarcialupi

Situated in the heart of the historical center of Castellina in Chianti, you will find the 15th century Palazzo Squarcialupi.

Castellina, Chianti , Sienna , Tuscany, Italy
Tel. + 39 0577 741186  Email:

In the past, the Palace was a noble residence with surrounding farmland and has recently been restored and reopened as a luxury hotel . Underneath the main building, in the ancient vaults are the antique wine-cellars where wine is produced to this day from the grapes grown in the vineyards surrounding the village. These ancient underground stone tunnels have also provided the idea location for Palazzo Squarcialupi’s spa.

The hotel, with 15 rooms, two Superior rooms and three elegant lounges, transports you into a medieval world, offering the maximum comfort for a pleasant and relaxing stay.  At the hotel bar, small enoteca and at the panoramic terrace, guests can taste the hotel’s own wines whilst admiring the magnificent scenery of the Chianti hillside. The hotel also has a swimming-pool in its spacious garden, and guests can enjoy pleasant walks through 170 hectars of woods and vineyards which surround the property.

Palazzo Squarcialupi can be booked as part of a tailor-made itinerary. Please contact us at for more information.

Il Chiostro di Pienza

Il Chiostro di Pienza is an ancient Franciscan convent converted into a 4 star hotel in beautiful Pienza at the heart heart of the Val d’Orcia.

Pienza, Tuscany, Italy                                                                     Telephone: +39 0578 748129


Il Chiostro di Pienza is a historical Franciscan convent converted into a 4 star hotel in beautiful Pienza at the heart heart of the Val d’Orcia. The history of the hotel is linked to the history of Pienza itself, as the ancient building has played an important role in the development of this famous and enchanting Tuscan city. The Monastery of St. Francis was certainly the most important religious and cultural institution in old Corsignano, at least until the radical transformation of the city into Pienza in 1459 under Pope Pius II.

The historic pedigree of this unusual building is combined with great hospitality and comfortable rooms, which have views of the medieval town and the beautiful Val d’Orcia. While the hotel is in the city center, it boasts an outdoor swimming pool and a beautiful restaurant with an outstanding  view of  the Val D’Orcia hills. Guests can dine in the terraced garden of the old monastery, and enjoy Relais Chiostro’s  chef’s interpretations of the local Tuscan cooking, with its many scents and flavors, all sourced locally.

Il Chiostro di Pienza can be booked as part of a tailor-made itinerary. Please contact us at for more information.


Palazzo Ravizza

The Palazzo Ravizza is an elegant Historic Hotel in Siena

Siena, Tuscany, Italy
Email: Telephone. +39 0577 280462

Located in the historic centre of Siena and within walking distance to the famous Cathedral, Palazzo Ravizza is a convenient base to see the city, take heritage day trips and enjoy food and wine tours to the surrounding countryside of Chianti, Val d’Orcia and Crete Senesi, as well as to visit the famous hilltowns like Pienza, San Gimignano, Montepulciano and many others. The hotel boasts beautifully styled rooms, a lush tiered garden and gorgeous panoramic views of the Sienese countryside.

A stay at Palazzo Ravizza is a leap into the past: this historic building was converted into a hotel in 1924 and is still managed by the same family. It has mantained not only the style and classic ambiance of a heritage hotel but also the atmosphere of an elegant and welcoming private home. Within its renaissance walls, the Palazzo appears today the way it was arranged as a family residence in the 19th century and later as a Pensione in the 1920’s, retaining an elegant ambiance of classic design with antique family furniture, perfectly blended with the private and tranquil atmosphere of a home.

Palazzo Ravizza can be booked as part of a tailor-made itinerary. Please contact us at for more information.