Great Explorations

(800) 242-1825
(604) 730-1247

National Geographic






“We found the people we met made the trip so special. Several of us have already been talking about which trip to go on next year.”

– Kay & Jim D,
Burlington, VT

More testimonials


Trip Dates:

May 20-27
Sep 20-27

Self-guided and custom trips also available and can start any day. Call or email for details.

May 19-26
Sep 19-26


Trip Size:

8-12 participants

Total Days:

8 days / 7 nights


Montepulciano/ Siena


Albergo Il Marzocco, Montepulciano

Hotel San Gregorio, Pienza

Il Borgo Rocca D’orcia

Giglio Hotel Montalcino

Fattoria Pieve A Salti, Buenconvento

Hotel Chiusarelli, Siena

Activity Level:

10-24 km (6-15 miles) daily distance which will take 4-6 hours


Moderate hills


Land Cost (current year):
US $2350
Includes 7B/2L/6D

Single Supplement:
US $590


Tuscany, Walking

"...Birthplace of the Renaissance, land of Dante's poetry, and Chianti wine, Muse to Michelangelo..."


Tuscany is art. Perfectly proportioned villas framed by elegant cypresses cap lines of hills. Towns and villages display layers of heritage in stately palazzi, decorated window frames, even doorknockers and wine bottle labels. Picture yourself walking in Tuscany, and imagine the delights of a guided tour.



Getting there :
Montepulciano: You can reach Montepulciano from Chiusi by taxi which is 20km away. Airports convenient to Chiusi are at Rome and Florence. From Rome train travel to Chiusi takes between 1 and 1.5 hours. From Florence the trip takes approximately the same time, but may require a change in trains.

DAY 1:
Montepulciano - Arrival to your first accommodation in Montepulciano. Spend some time strolling around this beautiful town, with its many Renaissance palazzi and churches. (15 km distance/490 m total elevation gain)

DAY 2:

Pienza - Walk to the beautiful church of San Biagio on the outskirts of town, then head into the countryside. Stop at the walled village of Montichiello for lunch or enjoy an espresso before making your way to Pienza, a small town once called “the pearl of the Renaissance”. Partly redesigned by Pope Pius II, Pienza boasts a splendid Renaissance Cathedral and the charming Palazzo Piccolomini. Sample pecorino, a local sheeps’ cheese. (15 km/490 m total elevation gain)

DAY 3:
Rocca d’Orcia - Continue through a beautiful region of rolling hills, oak woods, and charming villages. Pass through San Quirico d’Orcia (409 m), another walled city with an elegant 12th century church and Bagno Vignoni, a spa town with a central square that has a huge steaming pool of sulfurous water famed for its healing properties since Roman times. End the day in the tiny village of Rocca d’Orcia. (21 km/685 m total elevation gain)

DAY 4:
Montalcino - On this challenging day, you will walk along dry riverbeds to reach the isolated Abbazia de Sant’Antimo, with its magnificent Romanesque church which the locals like to say was founded by Charlemagne in the 8th century. There are 10 more km to go before you get to today’s destination, Montalcino, so you’ll be picked up at the abbey and driven the rest of the way. (13 km/585 m total elevation gain)

DAY 5:

Buenconvento - Montalcino is renowned for its ruby-red Brunello wines, so you’ll spend much of the day strolling through vineyards as well as olive groves. Then you’ll enter the primeval landscape of the Crete Senesi , where shepherds tend the sheep whose milk is used to make pecorino cheese. Spend the night at a delightful agriturismo near Buenconvento. (23.5 km / 525 m total elevation gain)

DAY 6:

Buenconvento - Enjoy a leisurely day relaxing around the pool or follow a hilly path to the 14th-century Benedictine abbey of Monte Oliveto Maggiore, one of the most impressive abbeys in Italy. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. The walk back from the abbey takes 3 hours.

(10 km/255 m total elevation gain, beginning with a shuttle to Monte Oliveto Maggiore)

DAY 7:

Siena - Walk along a winding dirt road over hills and through oak woods. Pass Buenconvento and Murlo, a tiny medieval borgo, the oldest settlement in the area. A ring of houses forms Murlo’s defensive walls. Visit the Museo Etrusco which commemorates the town’s Etruscan origins. You’ll be met in Murlo and transferred to Siena. (16 km/285 m total elevation gain)

DAY 8: Enjoy the sights of Siena before your departure. Stroll through the Piazza del Campo and to the spectacular Duomo, one of the few full Gothic Cathedrals built south of the Alps.


  • What's Included
  • Weather
  • Ride Info
  • Map

Map of the Area

Ride Info

Siena Weather

What's Included in the Cost of Your Trip?

  • Services of one or more experienced Great Explorations guides and support vehicle
  • 7 nights lodging
  • All breakfasts, 2 lunches, and all dinners but 1
  • Entrance fees for selected historical sites and museums
  • Detailed map and route instructions
  • All baggage transportation
  • All transportation from initial meeting point to final drop-off (see arrive/depart cities)

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. Due to cancellations and waiting lists, trip availability fluctuates daily. If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at or by telephone at 604.730.1247



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