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8 Day Postcards of Tuscany Biking Tour 2019
time 8 Days / 6 Nights

When foreigners imagine Tuscany, the Chianti and Val d’Orcia are the places they envision. These picturesque rolling hills, stupendous vineyards and picture-perfect medieval towns have been widely celebrated in photographs, magazines and even in movies. The best way to see these places in all of their full glory? By bike. Prepare to be mesmerized by these postcards of Tuscany: the Chianti vineyards, cypress trees in the Val d'Orcia, the hills of Crete Senesi, the enchanting towns of Radda, Greve, Pienza, Montepulciano and more. Along the way, taste the vintages and typical local products that make this corner of Tuscany absolutely delicious, too!

inclusionAt a Glance
  • Depart US to Florence, Italy
  • Arrival in Florence, Transfer to Radda in Chianti
  • Radda - Greve - Panzano - Radda (about 31 miles - Altitude: 2700ft)
  • Radda - Gaiole in Chianti - Castello di Brolio – Radda (about 28 miles - Altitude: 2900ft)
  • Radda – Val d’Orcia – Crete Senesi - Pienza (22, 31 or 53 miles)
  • Pienza - Bagni Vignoni - San Quirico - Montalcino – Pienza (about 38 miles - Altitude: 3280ft)
  • Pienza - Monticchiello - Chianciano Terme - Montepulciano – Pienza (about 28 miles - Altitude: 2900ft)
  • Transfer to Florence, Depart Florence, Italy to US
dates Itinerary
Click on the plus sign for full day description.

Board your overnight flight and you're off to your exciting biking vacation in Tuscany! 
*Flights are not included in the price of this package.  We are happy to arrange them for you.

Arrive at Florence airport and private transfer to the hotel in Radda in Chianti. Afternoon free to explore the town. Short briefing with the tour guide. Dinner with local specialties and overnight at hotel.

After breakfast, you will meet your biking guide and set out into the heart of Chianti. Discover the secrets of this celebrated land of vineyards and olive grows. You will cycle to Greve, a charming town considered the capital of Chianti. Enjoy lunch, photo stops, coffee and some of the most beautiful vistas you will see in your life. Return to hotel for dinner and overnight.

Today is a great day of biking between small medieval towns. A special treat: you will taste wine made with ancient recipe of Hippocrates, called ippocrasso. Then you will continue to the town of Gaiole and visit to the imposing Castello di Brolio. Return to hotel for dinner and overnight.

After breakfast you will get ready for your next trip to the heart of the Val d'Orcia, a valley so beautiful that it has starred in several movies, including Ridley Scott’s film Gladiator. You will ride through the Crete Senesi, where wheat fields roll along as if they were waves. This panorama is breathtaking ... The total distance is long but with van support you can choose how much you want to pedal and how much you want to ride in the van. Dinner and overnight at hotel.

On today’s journey you will see one of Tuscany’s postcards – the town of San Quirico d’Orcia. You will continue to Bagni Vignoni, a charming spa town dating to Roman times. This small village only has 30 residents. The center of the town is a rectangular pool filled with hot water from volcanic origins. Back in the saddle, you will reach Montalcino where there are many opportunities to experience a good glass of Brunello! After lunch return to Pienza. Dinner and overnight at hotel.

Do you know that famous little road full of cypresses in the postcards of Tuscany? So ... let's go there today! Bring your camera! You will descend toward Montichiello for a brief visit and then you will pedal to the town of Chianciano ... with cinematic panoramas. In the city of Montepulcino you will take a break for lunch and free time to visit the city. Do not miss the famous Piazza Grande, where the Twilight film, New Moon was shot. Enjoy a visit to a winery with delicious wine tastings. Dinner and overnight at hotel.

Your Italy Vacation has come to an end as you transfer from your hotel in Pienza to Florence airport and head back home.