Walking the Tuscan Hills: Self-Guided

Self-guided tours are meant for independent travelers; people who are in for a little adventure but don’t like to be completely on their own. Self-guided tours give you freedom and flexibility as you can start whenever you want, every day of the week, any day of the month between March 1 and November 1. Your hotel is booked and always waiting for you! You are walking by yourself but with a very reliable set of road instructions and maps! And if you need it, assistance is only a phone call away! Tours are 8 days and 7 nights in length. This tour includes visits to Sienna, Montalpulciano, Montalcino, Pienza, San Quirico and Terme di Bagno Vignoni; Abbey of St. Antimo and the superb Monastery of Monte Oliveto; exquisite medieval villages, century-old farms and churches; sweeping views over the breathtaking Tuscan landscape; a patchwork of wine groves and olive trees; visits to the wine regions of “Brunello” and “Nobile”, mild climate and delectable Tuscan food.

Daily Itinerary

Day 1 – Arrival in Chiusi Day 1:
You are welcomed by our representative at the train station in Chiusi for the transfer to your comfortable hotel in Montepulciano. Here he will go over the tour with you, supply an information package, answer your questions and give you a few tips!

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 takes you to lovely Montichiello, a nice little village immersed in the “Crete”, the region In Tuscany with clay hills and grand open valleys. You can stop here for a tasty Tuscan lunch or just for 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 by request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight; the cathedral and the Pope’s residence are well worth a visit. Overnight in a pleasant hotel in town.

Day 3 – Pienza to San Quirico d’Orcia to Bagno Vignoni (5 hours walking time)
We 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, little village including the Horti Leonini, a large, 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 will definitely want to take a short resting stop to admire the spectacular view! From Vignoni you wind your way down to other points of interest in the beautiful Orcia Valley: the stony, shallow 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, appreciated since Roman times, that bubble up into a large pool constructed by the Medici family in the picturesque 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)
You’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. Here you can still hear the original Gregorian Chants sung by the 5 remaining monks in the abbey. In the evening you will reach Montalcino, the capital of Brunello wine ; It is a nice medieval town with plenty of shopping possibilities well worth spending some leisurely time. Night in a hotel in Montalcino.

Day 5 – Montalcino to Buonconvento – (4 hours of walking)
Today you 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” landscape. In this case, you will 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 on one hand, and along the route of the all-important medieval Via Francigena Pilgrim Route on the other.

Day 6 – Buonconvento Roundtrip (3.5 hours of walking time)
This short day is full of up and downs. 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 though some monks remain as caretakers. Century 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 will start the day with a transfer to the monastery so you can visit the abbey before the tourist rush hours and 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 to Siena (5 hours walking time)
Today you can either walk or be transferred to your hotel in Siena. If you decid to walk, you will be transferred to Grancia di Cuna and then you can walk to the hotel in Siena. After Florence, Siena, once Florence’s most powerful rival, is by far the most interesting town in Tuscany and because of its many treasures two days are recommended 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.

Day 8 – Departure from Siena
Tour ends after breakfast. The train station in Sienna, 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. Enjoy your last night of the tour!

Getting There

You are welcomed by our representative at the train station in Chiusi for the transfer to your comfortable hotel in Montepulciano. Chiusi is on the main line between Rome and Florence. Some trains have a direct connection with Milan. Please note that Chiusi is quite a bit closer to Rome than Milan and if you are able to fly directly to Rome it will be a shorter, easier connection to Chiusi. In either case, make sure your train stops in Chiusi. Please let us know the arrival time of your train at least one week before your trip! For train schedules visit the website of the Italian Railways, www.trenitalia.com or www.raileurope.com.


Daily breakfast is included

Prices and Dates

Check out “Italy Tours” in our SELF-GUIDED Tour Calendar

Tour Length

8 days/7 nights

      – 7 nights of double occupancy lodging in charming 3-star hotels with private facilities each night.
      – Daily breakfast
      – Luggage transfers
      – All transportation during the tour, except private transfer from last hotel
      – Emergency assistance telephone number
      – Route directions and maps
    – All taxes and gratuities for the hotel and restaurant portions of the tour
Level of Difficulty

The average distance is between 3 and 6 hours of walking per day. The terrain is moderately rolling with some short steep hills, upwards and downwards; walking is mostly on small footpaths and some country roads. Well fitting, supportive “broken in”, hiking boots are very strongly recommended for this tour, not because it involves dangerous mountain hiking but because they give a better grip on the occasionally loose, rocky surface. Tour rating is moderate to challenging.


– Airfare
– Alcoholic and bar beverages
– Lunches and dinners
– Private transportation from Buonconvento to Siena on day 7


In May and September the average daytime temperature is 70 F, in June 76 F.

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