“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 hiking in Tuscany, and imagine the delights of a guided tour.

Only Great Explorations:

  • Small groups, extraordinary guides, and authentic experiences
  • Order off the menu at restaurants you won’t find in guidebooks
  • Distinctive, charming hotels too small for larger groups
  • We design and operate our own trips so there are only good surprises




Day 1



Day 2

Rocca d’Orcia

Rocca d’Orcia

Day 3






Day 5+6


Siena, Province of Siena, Italy

Day 7+8

What’s Included in the Cost of Your Trip?


Services of one or more experienced Great Explorations guides
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




May 12-19
Sep 12-19


Dates available upon request

Trip can start at any date. Custom and self-guided trips also available. Call or email for details.


4-12 participants


8 days / 7 nights


Montepulciano / Siena


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


Moderate hills


Land Cost:
US $3,450
Includes 7B/2L/6D

Single Supplement:
US $860

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 info@great-explorations.com or by telephone at 604.730.1247.

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


Arrival to your first accommodation in Montepulciano. Spend some time strolling around this beautiful town, with its many Renaissance palazzi and churches.

Hiking Distance: 15 km, 490 m total elevation gain.


Day 2


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.

Hiking Distance: 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.

Hiking Distance: 21 km, 685 m total elevation gain.


Day 4


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.

Hiking Distance: 13 km, 585 m total elevation gain.


Day 5


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 Buonconvento.

Hiking Distance: 23.5 km, 525 m total elevation gain.


Day 6


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.

Hiking Distance: 10 km, 255 m total elevation gain (beginning with a shuttle to Monte Oliveto Maggiore).


Day 7


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.

Hiking Distance: 16 km, 285 m total elevation gain.


Day 8

Departure Day

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.

Albergo Il Marzocco, Montepulciano

The 16th Century hotel has been run by the same family for over 100 years and is an ideal place for a peaceful relaxing stay. The spacious and comfortable rooms open to wide lounges that are furnished with 19th century pieces. Guest rooms have either balconies or terraces with valley views, or window views of old town’s Renaissance homes.

Hotel San Gregorio, Pienza

This 3 star hotel is conveniently located steps to the historical district of Pienzain in the heart of Tuscany. All rooms are finely furnished suites complete with sitting rooms and Jacuzzi tubs. A new swimming pool and restaurant were added in 2007 making this an extremely comfortable hotel.

Giglio Hotel, Montalcino

This charming family-run hotel is in the heart of Montalcino, and boasts spectacular views over the Tuscan countryside. Rooms feature cast-iron beds, frescoed ceilings and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance.

La Cisterna Nel Borgo, Rocca D’orcia

This charming and cosy albergo has only three rooms decorated with tradition and taste. It also has one of the best restaurant in the area.

Fattoria Pieve A Salti, Buenconvento

This beautiful traditional Agriturismo (country hotel) boasts a spa, horse riding and outdoor & indoor swimming pools. Rooms are comfortable and decorated in rustic Tuscan style, complete with wrought iron beds. There is a traditional tuscan restaurant on site, where organic food is served.

Hotel Chiusarelli, Siena

This 3 star hotel is situated in the heart of Siena, just 300 meters from the Famous Piazza del Campo. Housed in an ornate 19th century historic building, the rooms have all been refurnished with Italian Neo-Classic style. From the guestrooms enjoy lovely views over the rooftops or of an open green park.