Tuscany Walking Adventure

October 24 - 30, 2021

“Life offers you a thousand chances … all you have to do is take one.” 

 Frances Mayes, Under the Tuscan Sun

Italy is an amazing country. Tuscany is perhaps its most vibrant, beautiful province. With sights ranging from the arts center of Florence to the leaning tower of Pisa to the wine region of Chianti, there is much to see and do in this central region of the country.

Yet having traveled and run tours throughout Italy, we can honestly say one of the most incredibly beautiful areas of the country is southeast of Siena in the Val d’Orcia. It is a hauntingly picturesque region of rolling hills and dirt roads dotted with the medieval towns of Montepulciano, Pienza, and Montalcino. Go ahead – type Val d’Orcia into your search engine, click on Images, and see if you agree this is one of the most beautiful regions of the world!

This area of Tuscany is not fast-paced. It takes time to grow the grapes to produce the famous Brunello di Montalcino and Vino Nobile di Montepulciano wines and to age the delicious Pecorino sheep’s cheese. Local citizens make it a priority to say hello to their neighbors and to chat over a morning cup of Cappuccino. The “slow” movement, which emphasizes connections to local food, people, and places, was created in Italy and comes alive in this region of Tuscany.

In keeping with that ethos, we believe walking is the best way to see this region and experience everything it has to offer. The paths – mostly gravel and with few cars – take us to the real Tuscany full of farmhouses, fields, hilltop towns, and old churches. The pace makes it not only possible but almost imperative to connect with locals along the way. And getting a little fresh air and exercise is not only good for our health and happiness but makes that bowl of pasta, white bean soup, or crostini doused in olive oil that much more rewarding at the end of the day.

On this Tuscany Walking Adventure, we accommodate various fitness levels as always. We average about 14 kilometers or eight miles per day, which is usually plenty for a weeklong tour yet moderate enough that most people can complete each walk. However, if you need a lift we always have our support van nearby. You can choose to walk as a group with our guides or head out on your own some days using our GPS directions on your phone. You can even skip a day of walking to meander the ancient streets of one of the local towns, in keeping with the Slow movement.

Combine the beauty of the Val d’Orcia, the amazing cities of Montepulciano, Pienza, Montalcino, and Siena, abundant good food and wine, and the loveliest walking paths you can imagine and you can see why we are in love with this new Tuscany Walking Adventure.

Private Tour Info

Private tours are offered with two guides, one walking and one driving a support van, with a minimum of ten people. If your group is comfortable walking on its own using our GPS routes, we can run this tour with as few as six people and one guide.

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Trip Highlights

  • Beautiful landscapes of rolling hills, quaint villages, and waving wheat fields
  • Incredible cuisine: pastas, pizza, and bruschetta...Pecorino cheese...olive oil like you have never tasted before...all capped with a little gelato or limoncello!
  • Winding streets in the medieval towns of Montepulciano, Pienza, and Montalcino
  • Finish in the thriving, culturally rich city of Siena

We meet after lunch in the beautiful town of Montepulciano, a medieval city full of winding, cobblestoned streets and boasting plenty of shops, restaurants, and cafes. The city, which has ancient roots dating back to Roman times and the pre-Roman Etruscan people, is strategically placed on a hillside with a castle that protected the trade routes and farming fields below. We will take an introductory exploratory walk on the side roads and small paths of the city and the countryside just below, with a stop at the Cantina Dei winery for our first taste of Vino Nobile di Montepulciano. This night we will eat a delicious Italian meal together, as we will each night of the tour.
Walking Distance: 5 KM


This is our first classic Tuscan walk, with views of lovely small towns as we amble across the countryside of rolling hills, dotted by stone houses and cypress trees. Our walk takes us into the medieval walled village of Monticchiello. After exploring this cute village, you can opt to eat on your own in town, with one option being at Ristorante Dario, who is a good friend of our guide Giovanni, or Osteria la Porta which has a beautiful view over the Val d'Orcia below. Don't eat too much because after lunch it is back down into the valley and on to the Podere di Casale goat and sheep cheese making farm. We then walk up again to the small hilltop city of Pienza. When Silvio Piccolomini became Pope Pius II in 1458 (before Columbus reached America), he decided to create a model Renaissance town and the resulting Pienza still boasts the central piazza, the towering cathedral, and the parks overlooking the valley below. In Pienza, Marco and his family have hosted our groups at his Piccolo Hotel for years and we'll be happy to rest while toasting the sunset from the hotel garden.
Walking Distance: 14 KM


After breakfast we will descend from Pienza into the scenic Orcia river valley, walking through postcard landscapes of rolling hills and deep golden wheat fields. Along the route we will pass through the village of San Quirico d'Orcia, which has much of its ancient wall systems remaining but since it is often overlooked by tourists, seems more real than some of the nearby towns. You will be able to explore the town and eat lunch on your own. Ristorante Trattoria Al Vecchio Forno is a good option. First you might choose to visit the Birrificio (brewery) San Quirico, where you can sample Italian-style craft beers - think fruity, spiced, and amber rather than hop-heavy IPAs. After lunch we continue our walk to Bagno Vignoni, a beautiful "resort" town famous for its hot springs, where the traditional piazza is instead a large pool. You can choose to soak in the public Parco dei Mulini or in the private baths connected to our hotel, the Hotel le Terme.
Walking Distance: 14 KM


Today we depart the Val d'Orcia and head into new scenery, passing through evergreen woods and next to vineyards on small paths and country roads. En route we will visit the Mastrojanni winery to learn about and taste the famous Brunello di Montalcino wines. After the tasting we will stop in the small village of Castelnuovo, which has a number of lunch options. Our destination in the afternoon is the Abbey of St. Antimo, a beautiful church founded by Charlemagne in 781, which has inspired many poets and painters and where Benedictine monks chant daily. Because of the length of walk to the abbey (perfect!) and the absence of nearby lodging, we will shuttle in the van to our hotel tonight in Montalcino, another beautiful medieval town and famous for both its Fortezza (fortress) and the sublime Brunello di Montalcino wine we tried earlier in the afternoon.
Walking Distance: 14 KM


We start our walk heading downhill out of Montalcino, passing some of the vineyards that make the local wine so famous. Our track is on small gravel roads and dirt walking paths, through forests and countryside dotted with farmhouses. Lunch will be at the town of Buonconvento, a charming spot off the normal tourist route and a great place to see real small-town life in Italy. The small city is intriguing, having been built not on a hilltop but instead in a valley at the confluence of two rivers, an important location for trade. The walled town is perfect for exploring and finding a bite for lunch. After lunch we will head uphill to the lovely agriturismo of Pieve a Salti, a working farm that houses guests. Daniela and her crew have been hosting us here for years, and the farm's delicious home-grown products make for a fresh-as-can-be dinner.
Walking Distance: 15 KM


We start heading downhill from the ridge top location of Pieve a Salti, walking on small paths through the forest. We then reverse and start climbing uphill to the Abbazia di Monte Oliveto, an abbey founded in 1313 by a Sienese nobleman. The still-operating abbey is a Benedictine order monastery with world-renowned frescoes and carvings by Sodoma, Signorelli, and Fra Giovanni da Verona. After a visit to the monastery, we will shuttle to Siena, considered by some to be the best preserved medieval city in Europe, a true masterpiece of art and architecture with its Gothic Duomo, museums, and famous buildings. If you have time this afternoon, our guide can take you to the Museo Civico Siena, housed in the Palazzo Pubblico, a building built around the end of the 12th century to house the nine lords who ruled the Republic of Siena. The museum has frescoes from the 12th and 13th centuries.
Walking Distance: 12 KM


On our final day, we eat breakfast and then enjoy a walk of Siena, discovering the ancient buildings and the untrammeled side alleys. We'll visit the shell-shaped square "Il Campo", the scene of the mad horserace "The Palio" which you might have heard or read about. We'll also stop at the Torre del Mangia, an 87 meter high tower built in the 1300s. After our walk, we will check out of the hotel. You are free to continue on your journey, stay another night in Siena, or head back towards the airports of Rome or Florence.
Walking Distance: 3 KM

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Trip Accommodations


This hotel is located inside the medieval walls, a few meters from Porta al Prato (the main gate of town). Built in 1500, it became a hotel in 1870 and has been managed by the same family since the beginning of the 1900s!


This elegant hotel is built in the historic center of Pienza, a UNESCO World Heritage site, and is situated inside the city walls, with sweeping views over the valley below. The property was formerly Franciscan Convent dating back to the 13th century.


This hotel has a history hosting travelers dating back to the 1800s. Located in the center of the gorgeous town of Montalcino, the family-run hotel is a perfect place to explore the old town.


This working farm has simple accommodations but the highlight is being out in the middle of nowhere on a ridge overlooking the valleys on each side. Well, perhaps that is the secondary highlight after the meal made from local products and estate wine.


Built in 1870 as a neoclassical style villa, the hotel was completed renovated in 2013. The frescoed walls integrate with the modern luxuries and the central location is the perfect hub from which to explore one of Italy's most incredible towns.

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Arrival & Departure

We meet you after lunch on the first day of the tour in Montepulciano. You can reach Montepulciano by train from Rome (two to 2.5 hours with one connection), Florence (two hours with one connection), or Siena (one hour direct train). We finish in the late morning of the last day in Siena, which has direct 1.5 hour trains to Florence or 3.5 hour trains with one connection to reach Rome. You might also consider renting a car before or after the tour, as having a private vehicle is the best way to tour Tuscany if you plan to spend extra time in the area.

What's Included
  • Two Zephyr guides accompany each trip, with a third added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
  • All of your dinners and breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • All group activities are included.
  • NOT INCLUDED Beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.

The temperature in Tuscany at the end of October is usually pleasant, with daytime highs around 60 degrees Fahrenheit. Given the absence of tourist crowds, it is an ideal time to be in the area. It does rain in October and temperatures can vary, so you should be prepared for all eventualities.

Extending Your Vacation

If you are interested in ancient monuments, visit Rome for sure.  If you are interested in art, spend time in Florence and see Michelangelo’s David sculpture (and much more!).  If you want to check the Leaning Tower of Pisa off your list, it is not far away. We think one of the best things to do is just rent a car and drive among the small towns of Tuscany or neighboring Umbria.

Route Directions

All routes are now on GPS and you have the option to download these routes onto your cell phone or simply stay with your guide.

Ability Level

This trip is rated as For All Abilities. The walks have rolling hills but no mountains. The walking tracks are on paths, dirt roads, and gravel with good footing. You can generally cut any day's walk to whatever distance you wish, as we will have a support van available.

Type of Person Who Would Enjoy This Trip

This is a perfect tour for those of you wishing to explore Italy and Tuscany in depth, without the hurry that often comes with our daily lives. It has plenty of exercise for anyone but is not overly taxing. We cannot say enough about the scenery, the food, the wine, the ancient towns, and the culture of this area of Italy.

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