Tuscany straddles the gentle Apennine hills in the heart of Italy, where cypress trees, olive groves, vineyards, and soft, verdant hills create a landscape reminiscent of Renaissance paintings. Giotto, Michelangelo, and Leonardo da Vinci traveled the same landscapes centuries ago, and fortunately, not much has changed. Their influence is evident in many towns and villages along the route, and as you ride quiet routes along sun-drenched ridges, you will enjoy expansive views over the landscape of their inspiration.
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.
- 2009 Guided Dates: May 3-10; May 24-31; Jun 21-28; Sep 12-19; Sep 20-27 Call to check for updates or to add a new date.
- 2010 Guided Dates: May 2-9, 23-30; Jun 20-27; Sep 19-26. Call to check for updates or to add a new date.
- Tour starts: Siena train terminal 1500hrs or Poggibonsi train terminal. 1600hrs.
- Tour finish: 1000hrs Chiusi Train Terminal, near Montepulciano.
- 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.
Tour Itinerary:
Day 1: Pick-up at the Seina train station at 3:00pm or at Poggibonsi train station at 4:00pm, for a transfer to your idyllic hideaway in the Rennaissance gem of San Gimignano – town of medieval towers, high in the Chianti hills. Dinner included on guided trips only. Lodging: Hotel La Cisterna, San Gimignano.
Day 2: Ride one of three loop options (30, 52, or 62 km) from San Gimignano. 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. Breakfast included. Light lunch picnic is included on guided trips. Lodging: same as last night.
Day 3: An exhilarating 65 km through forest and field on some of the least traveled roads in the region. You will ride through several 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. Breakfast included. All meals are included on guided trips. Lodging: Relais Fattoria Vignale, Radda in Chianti.
Day 4: A 65 km loop ride in the delightful hills of Chianti. Descend through the Chianti hills, 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 biggest wine producers of the area. Wine tasting, lunch, and a short ride back to your inn await you. Breakfast included. Light picnic on guided trips. Dinner is independent tonight. Lodging: same as last night.
Day 5: 84 km. A long and delightful 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 & '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. Breakfast included. Picnic lunch and dinner is included on guided trips. Lodging: Locanda La Costa, Montefollonico.
Day 6: 62 km. 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 church of San Bernardo (18th century), Palazo Bucelli, with its Etruscan and Latin inscriptions in the lower walls, and the famous Montepulciano Piazza Grande, surrounded by 14th & 15th century buildings.
You’ll also have the opportunity to explore Pienza, which served as the set of Zefferelli's Romeo and Juliet, and more recently as the area The English Patient was filmed. This ideal town was a dream of Pope Pius II, who died before its completion; however, despite passage of time the harmony he felt has not been disturbed. Breakfast included. Picnic lunch also included on guided trips. Independent dinner in Montepulciano. odging: Relais Il Chiostro di Pienza, Pienza or Podere Dionora.
Day 7: 72 km. 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 will 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. Breakfast included. Dinner is included on guided trips. Lodging: same as last night.
Day 8: Morning transfer to Chiusi-Chianciano train terminal (a stop on all major Florence-Rome lines).
Notes:
Airfare is not included in the tour price.
Prices:
- Guided Cost: $3495 (per person, includes 8 days, 7 nights, 7 breakfasts, 6 light picnic lunches, 4 dinners, guide & van support, maps & route notes, luggage handling, taxes).
- Self-Guided Cost: $2895 (per person, includes 8 days, 7 nights, 7 breakfasts, maps & route notes, luggage handling, 2 transfers, taxes).
Note: All prices subject to change.
Also see tour packages in:
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Italy
Outdoor: Land Rambler
Bicycle Touring
Cultural Journey
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