Cycling Tuscany’s Wine Country

Our luxury 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.

Pienza ~ Montalcino ~ Chianti
Self Guided Tour, 7 Days/ 6 Nights,
Start any date September or October

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 Land
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 & Monte Oliveto Maggiore Abbey
Start today’s cycling offers a  long downhill  followed by a gentle ride to Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century. Following this, discover the fascinating area of Le Crete, Tuscany’s answer to the Badlands, where the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity. Distance 58 km/ 36 miles

Day 5: Chianti Hills
Reach Castellina in Chianti following the “Chiantigiana” road. Along the way you can stop at the commune of Castelnuovo Berardenga before a ride through the vineyard of the famous Chianti Classico wine and a stop at Castello di Brolio. Arrive in Radda for light lunch and enjoy the last 10 km of gentle rolling hills before arriving in Castellina. Distance 50 km/31 miles

Day 6: Greve in Chianti & Panzano
Today’s bike ride takes you on a loop to Panzano. Cycle along quiet roads to the three villages that formed the Chianti Alliance centuries ago,  visit Tuscany’s forgotten abbeys and hamlets and then enjoy a winery tour. Have a stop at Greve’s main piazza before heading back via Panzano with its preserved old walls and gate. Distance 52km/32,5 miles

Day 7: Monteriggioni and Arrivederci!
On your last day, take a looped bike trip to Monteriggioni, literally a town-in-a castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Distance 30km/18,5 miles.

Trip Includes:
Six nights in  four & three-star hotels
Six  breakfasts
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in Castellina
Keepsake water bottle
Sales taxes

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

Bike Hire Extra

Choose from:
Hybrid/Touring bike:  Euro 180
High-end Road bike: Euro 210
E-Bike: Euro 210

Not included: Airfare to Italy, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.