Day 1 – Arrival in Poggibonsi
You will be met by our Italian representative who will drive you to your accommodations for the night, Villa San Lucchese. This is a beautiful villa near Castellina in Chianti and is also known for excellent food.
Day 2 – Monteriggioni/Colle Vald’Elsa/San Gimignano – Distance: 37 Km, Elevation gain: 590 meters
Your first day of cycling takes you to Monteriggioni, a perfect fortress town built in the 13th century and totally encircled by high walls with 14 heavily fortified watchtowers. Continue to Colle de Val d’Elsa, take time to visit some of the glass-blowing workshops. Then it’s on to San Gimignano, the “city of beautiful towers” and one of the best-preserved medieval towns in Italy before you head back to Villa San Lucchese.
Day 3 – Villa San Lucchese/Castellina in Chianti/Siena – Distance: 35 Km, Elevation gain: 500 meters
Follow winding roads through the Chianti countryside, past lush vineyards and superb wineries, to Siena, one of the most beautiful cities in Italy. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for dinner.
Day 4 – Siena/Buonconvento – Distance: 40 Km, Elevation gain: 570 meters
Winding on the Chianti country roads is quite dramatic as the landscape changes from the lush vineyards to the more linear cypress-crested hills of the “Crete” near Buonconvento. Here shepherds tend the sheep whose milk is used to make pecorino cheese. You will pass through the tiny borgo of Murlo, the oldest settlement in the area, before arriving at today’s destination, a delightful agriturismo just 3 km from Buonconvento.
Day 5 – Buonconvento/Montalcino – 40 Km, Elevation gain: 700 meters
After a steep climb, pedal through the spectacular eroded hills of “Crete” and then through thick cypresses and olive groves as you approach the 14th-century Benedictine monastery of Monte Oliveto Maggiore. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. Then continue to Montalcino, a classic Tuscan hilltown renowned for its ruby-red Brunello wines, considered by some to be the finest in Italy.
Day 6 – Montalcino/Sant’Antimo/Montalcino (your choice of mileage for the day as you will not be changing hotels tonight)
Long Distance: 52 km, Elevation Gain: 1,100 meters Shorter out and back option: 22 km, Elevation gain: 440 meters
Stroll around the town before following the trail to the abbey of Sant’Antimo, 10 km away. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque. With luck, you’ll visit at a time when the monks celebrate mass and the church echoes with Gregorian chants. Then return to Montalcino where you spend a second night.
Day 7 – Montalcino/Montepulciano – Distance: 50 Km, Elevation gain: 875 meters
You pass through many wonderful places today. Pause at the hot sulfurous pool in the piazza at Bagno Vignoni, then continue to Pienza, a Renaissance jewel and birthplace of Aeneas Sylvius Piccolomini who completely redesigned its center after he became Pope Pius II. Relax over a cappuccino in Montichello, a tiny walled village, and then head for beautiful Montepulciano, one of Tuscany’s highest hilltop towns and famous for its red Vino Nobile wines.
Stroll around Montepulciano before departure. Today you will be transferred to the Chiusi train station that has access to Rome, Florence or Milan.
** Shorter itineraries available.