Beginning near Florence with a pickup at Poggibonsi or Siena, you will spend the first two nights in spectacular San Gimignano, famous for its abundance of stone towers. You will then cross to the Chiantigiana route through the premier wine region of Chianti. On your way toward the hills of Southern Tuscany, you will have ample opportunity to sample wine and honey, as well as being fuelled by the gastronomic indulgence of some of the region’s finest chefs.
After visiting Montepulciano and Montalcino, tasting what are perhaps Italy's most complex wines-the Vino Nobile and Brunello di Montalcino, and stopping to listen to the Gregorian monks chanting in an awe-inspiring cathedral, you will enjoy the evening ambience of your peaceful hotel in Pienza. Custom groups any time. If you can spare some extra time, we recommend that you plan to spend a day or more in Siena or Florence before or after your adventure, to see the riches this ancient these cities have on display.
Day 1: Pick-up at the Siena train station at 15:00, or at Poggibonsi train station at 16:00, for a transfer to your idyllic hideaway in the Rennaissance gem of San Gimignano – town of medieval towers, high in the Chianti hills. Includes: (D). (Meal inclusions provided for guided trips. Self-guided trips include breakfast only) Hotel La Cisterna; or Hotel L’Antico Pozzo, San Gimignano.
Day 2: Ride one of three loop options (30, 52, or 62 km/19, 33, or 40 miles). This is a wonderful introduction to the Tuscan countryside, with opportunities for wine tasting, idyllic picnics, and such an abundance of intriguing smells that your head will reel with delight. Includes: (B), (L). Same lodging.
Day 3: 50 km/32 miles. An exhilarating ride through forest and field on some of the least traveled roads in the region. You will ride through quiet villages, each with its share of history, character and charm, unique to this corner of the world. Linari and Piazza are two of the smaller villages often missed - you may visit both on your way to Radda in Chianti. Includes: (B), (L), (D). Relais Fattoria Vignale, Radda in Chianti.
Day 4: 65 km/41 miles. A loop ride in the delightful hills of Chianti, with choices about whether you go to the highest point in Chianti at Monte Luco, or a more leisurely pedal through vineyards and olive groves, followed by a visit to Castelli di Brolio, one of the most respected wine producers of the area. Wine tasting, lunch, and a short ride back to your inn await you. Includes: (B), (L).
Day 5: 84 km/53 miles. A challenging ride along the ridge road to Asciano, then through gentle cypress-lined lanes to the southern Tuscan hills finishing just outside Montepulciano and Pienza. In this area, you’ll have chances to try the famous Vino Nobile di Montepulciano, famous as far back as the year 790! The '97 and '98 vintages are said to be the best in over 50 years! You will stop for lunch near the Abbaie di Monte Oliveto Maggiore, where you can visit renaissance frescoes, the cloisters, and bask in the mid-day peacefulness. Includes: (B), (L), (D).
Locanda La Costa, Montefollonico.
Day 6: 62 km/40 miles. A loop ride through some of the finest hill towns of Southern Tuscany. You’ll visit Montefollonico, Monticchiello, Castellúccio, and a village where much of the English Patient was filmed. While in Montepulciano you’ll have the opportunity to visit the little 18th century church of San Bernardo, Palazo Bucelli, with its Etruscan and Latin inscriptions in the lower walls and, the famous Montepulciano Piazza Grande which is surrounded by 14th and 15th century buildings. You’ll also have the opportunity to explore Pienza, which served as the set of Zefferelli's Romeo and Juliet. This ideal town was a dream of Pope Pius II, who died before its completion. However, despite the passage of time the harmony he felt has not been disturbed. Includes: (B), (L). Relais Il Chiostro di Pienza, Pienza; or Podere Dionora, Montepulciano.
Day 7: 72 km/45 miles. You’ll follow a delightfully quiet route as you make your way to the Roman Baths of Bagno Vignoni, where the Town Square is a thermal spring. You’ll then cross the hilly Val d’Orcia, stopping to reflect upon life at the abbey in San Ántimo, where you may hear the monks sing Gregorian chants. You can stop for a walk and lunch in Montalcino, buy some wine and honey at the castle, then ride downhill toward San Quirico d’Orcia and back to your hotel to prepare for our final feast together. Includes: (B), (D). Same lodging.
Day 8: Following your breakfast, there is a morning transfer to Chiusi-Chianciano train terminal (a stop on all major Florence-Rome lines). Includes: (B).
- Route Notes: Most of the route is well paved, but there are a couple of short gravel stretches. There are hills, and “rewards”. Relaxed riders are assisted with van support on longer climbs.
- Self-Guided Dates: You choose! We confirm within 48 hours.
- Start: Siena train terminal 15:00, or Poggibonsi train terminal 16:00, day one
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