Walking the Tuscan Hills - Self Guided Walking Tour - Van Gogh Tours

Walking the Tuscan Hills

From: $1,320 USD

8 Days / 7 Nights
Type: Self-Guided
Level of Difficulty: Challenging

Imagine Yourself…

  • Passing by scenic vineyards and shimmering olive tree orchards
  • Following a small country road to the tiny almost abandoned village of Alto Vignoni
  • Gazing up at the famous stained glass windows of a 13th century church
  • Dining on fine local Tuscan cuisine
  • Overnighting in a gorgeous typically-Tuscan “agriturismo”


Van Gogh Tours - Walking the Tuscan Hills Italy - Self Guided Cycle TourExplore the stunning hills of Tuscany on foot and uncover its charming villages, interesting history, and delicious cuisine. On this tour you’ll walk through the classic Tuscan landscape of vineyards, olive groves, farms, and cypress trees. You’ll visit some of the region’s most famous towns and some smaller villages – including Sienna, Montepulciano, Montalcino, Pienza, San Quirico, and Terme di Bagno Vignoni. The route will lead you to old and impressive churches, including the famous Monastery of Monte Oliveto and the Abbey of St. Antimo. Climbing the hills, you’ll enjoy sweeping views over this lovely landscape, and your path will take you to the wine regions of Brunello and Nobile. There’ll be plenty of opportunities to sample delicious local wines and classic, delectable Tuscan dishes!

Daily Itinerary

  • DAY 1 - Arrival in Montepulciano

    You will be welcomed by us at the train station in Montepulciano for the transfer to your comfortable hotel. Here, we’ll go over the tour with you, supply an information package, answer your questions, and give you a few tips! The rest of the day you can explore Montepulciano to walk Il Corso and explore these side streets. You’ll come across small restaurants, boutique shops, and quiet corners away from the busier areas. 

  • DAY 2 - Montepulciano to Pienza (5 hours walking time)

    From the San Biagio Church, which is in the outskirts of town (and certainly worth a visit), the dirt road will take you to lovely Monticchiello, a nice little village immersed in the Italian Crete Senesi, the region In Tuscany with clay hills and grand open valleys. We can stop here for a tasty Tuscan lunch or just a cappuccino before continuing on to the perfect Renaissance town of Pienza, an architectural jewel famous also for its cheese, the pecorino di Pienza. Pienza was planned and built from 1459 – 1462 by the famous Florentine architect Gambarelli at the request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight, and the cathedral and Pope’s residence are well worth a visit. You’ll stay tonight in a pleasant hotel in town.

  • DAY 3 - Pienza to San Quirico d'Orcia to Bagno Vignoni (4.5 hours walking time)

    We’ll leave Pienza today on a dirt road toward the village of San Quirico d’Orcia. This fortified village is one of the least known and best-preserved historical centers in the Sienese Province. It was an important stop for pilgrims on the Via Cassia, the way to Rome. The 15th century walls are still almost totally intact. They enclose the magnificent 13th century Romanesque Collegiate Church with a famous stained glass window and hand carved wooden choir-stalls. The main street of San Quirico, Via Dante Alighieri, traverses the town and contains a number of well-preserved medieval houses. Most notable is the Renaissance Palazzo Pretorio. There is plenty to see and photograph in this quaint village, including the Horti Leonini, an unusual public park with a Renaissance style garden created by Diomede Leoni in 1580. From San Quirico, a small road leads up through beautiful countryside to the tiny village of Alto Vignoni, now almost totally abandoned. It has a truncated medieval tower and a Romanesque church on the edge of the hill. You’ll definitely want to take a short stop to admire the spectacular view! From Vignoni, we’ll wind our way down to other points of interest in the beautiful Orcia Valley: the stony river bed, the castle of Ripa d’Orcia, and the ancient spa of Bagno Vignoni. Here you can soak your feet in the warm sulphurous waters that bubble up into a large pool constructed by the Medici family in the Piazza. Tonight you’ll stay in Bagno Vignoni or in an agriturismo 2 km from town along your trail.

  • DAY 4 - Bagno Vignoni - Sant'Antimo – Montalcino (5 hours walking time)

    We’ll have a beautiful but quite strenuous day of walking today along dry river beds in a rather wild but stunningly beautiful landscape to reach the inspiring Benedictine Abbey of Sant’Antimo. The Abbey was founded by Charlemagne and had a period of great splendor in the first centuries of this millennium. You can still hear the original Gregorian Chants sung by the 5 remaining monks in the abbey. In the evening we’ll reach Montalcino, the capital of Brunello wine. It’s a nice medieval town with plenty of shopping possibilities. You’ll stay tonight in a hotel in Montalcino.

  • DAY 5 - Montalcino to Buonconvento - (4 hours of walking)

    Today we will be walking through scenic Brunello vineyards and shimmering olive tree orchards. You can choose a shorter version, spending the night in a 3-star hotel in Buonconvento, or a longer route through a beautiful Crete Senesi landscape where you’ll spend the night in a nice agriturismo 3 km from Buonconvento. Buonconvento is an important agricultural center on the gentler side of the Sienese Clay Hills. It already flourished in ancient times, thanks to its particular geographical situation at the confluence of the Arbia and Ombrone rivers and along the all-important medieval Via Francigena Pilgrim Route on the other.

  • DAY 6 - Buonconvento Round Trip  (3.5 hours of walking time)

    This short day is full of rises and dips. Oliveto Maggiore is one of the best known Benedictine monasteries in Tuscany. The monastery was founded for hermits in 1313 and was suppressed by Napoleon in 1810. After restoration, it was made a national monument with some monks remaining as caretakers. Old pines surround the cloister and the walls are decorated with gorgeous, well-preserved frescoes detailing the history of St. Benedetto and the Benedictine order. Because of the monastery closing time you’ll start the day with a transfer so you can visit the abbey before the tourist rush hours, then start walking back toward your hotel or agriturismo. You can stop for a light snack at Chiusure, the first village on your way back. There is a small “Alimentari” which now has upgraded to a wooden terrace where they serve delicious, freshly made panini. 

  • DAY 7 - Buonconvento- Siena (5 hours walking time)

    After Florence, Siena, once Florence’s most powerful rival, is by far the most interesting town in Tuscany. Because of its many treasures we recommend two days here for an adequate visit. Highlights are the dazzling cathedral and the Palazzo Pubblico, both gorgeous Gothic buildings, and the Piazza del Campo, one of the most remarkable squares in Italy and the site of the yearly “Palio” horse races. Enjoy your last night of your tour!

  • DAY 8 - Tour Ends

    Your tour ends after breakfast with departure from Siena. The train station in Siena, where you might like to catch a train to Florence, Rome, or Milan, is 5 minutes away by cab. Busses to Florence leave from the square right around the corner from the hotel.

Dates & Prices

Green = Open | Yellow = Limited | Red = Full




Solo Traveller


$ 1320

$ 1550

$ 1710

  • Prices are per person in US Dollars 
  • Choose your own starting date
  • This tour can be guided upon request
  • What's included

    • 7 nights of double occupancy lodging in charming 3-star hotels with private facilities
    • Daily breakfast
    • Luggage transfers
    • All transportation during the tour, except transfer from last hotel
    • Emergency assistance telephone number
    • GPX files
    • All taxes and gratuities for the hotel and restaurant portions of the tour
  • Meals

    Included in the tour price you’ll receive daily buffet breakfast. For the buffet breakfasts there’s an assortment of cold meats and cheeses, eggs, bread, jams, cereal, yogurt, fruit, coffee, and tea. For lunches you will be in a town so you can find lunch at a restaurant on your own. Dinner will be on your own, and you can choose one of many delicious restaurant options within easy walking distance from our hotel.

  • Not included

    • Airfare
    • Alcoholic and bar beverages
    • Lunches and dinners
    • Gratuities for the guide
    • Trip cancellation insurance


The accommodations listed below are examples of those usually used on the tour. Depending on availability, you may be booked in a different accommodation of equal quality.

Hotel Chiusarelli

Hotel Chiusarelli

  • Siena
  • Rooms renovated according to NeoClassical style
  • Walking distance to historical center


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