Rocca Aldobrandesca ruins, Sovana

View of Montalcino

Pienza in the springtime

A street cafe in Arezzo

Sunset in Siena

Val d'Orcia, central hilltop towns region

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Discover the Best of Tuscany’s Central Hilltop Towns

Our book covers hundreds of locations within Tuscany.

Here is a sample of some of our favorite places in the Central Hilltop Towns region of Tuscany:

Three of our favorite places to visit in the Central Hilltop Towns


Montalcino is perched high on a hill (567 meters, 1860 feet) with breathless panoramic views of acres of vineyards, rolling hills and the Arabia, Ombrone and L’Asso river valleys. On a clear day, you can see as far as Corsica, the islands of Elba and Giglio, the Tyrrhenian Sea and the Apuane Alps. In the near distance, you can see Pienza, Montepulciano, Monte Amiata and Siena.

Montalcino is a magnificent medieval town with walls dating from the thirteenth century. The fortress, an outstanding example of military architecture, was built in 1361. The oldest part of the village is located along the main street called Via Matteotti which widens into the Piazza del Popolo, the medieval town center. The Palazzo Communale, dating from the thirteenth century, is located where Via Matteotti enters the piazza. There is also a large loggia, or columned terrace, facing the opposite side of the piazza that is comprised of six round arches built in the fourteenth century.

The advent of Brunello wine production, starting in the 1970s and 80s, created an economic recovery as Montalcino embraced full-scale wine production. Although there were only eleven Brunello wineries in the 1960s, by 2000 there were more than 200. Castello Banfi was instrumental in bringing Brunello to a world stage through its clonal research and technological advances, lending Brunello a rich consistency treasured by wine connoisseurs everywhere.

In 1980, Brunello received the highest accolade with the granting of the coveted DOCG (Denominazione di Origine Controllata e Garantita) label.

Montalcino, like Montepulciano, is a wine town with a great view. The primary activities are wandering the medieval byways, viewing the wonderful scenery along the town walls and enjoying one of the many enotecas and great restaurants along the way.

Abbazia di Sant’Antimo

The road to Sant’Antimo goes south from Montalcino in the direction of Castelnuovo dell’Abate through gorgeous, hilly terrain covered with green fields, grapevines and olive groves. Sant’Antimo is approximately 15 km from Montalcino, and the drive to Sant’Antimo can be easily combined with a trip to Monte Amiata or with a trip to various wineries in the area.

As you approach Sant’Antimo, you will first notice it to the right if driving south from Montalcino. The vision of Sant’Antimo from afar is stunning, particularly if the sun is low on the horizon and casting long shadows over the landscape. Sant’Antimo is isolated within a beautiful landscape, with a view unsullied by any other structure.

The church itself, dating as far back as 781 AD, is magnificent, a pure and stately Romanesque edifice with clean lines and elegant simplicity. Charlemagne is said to have arrived at Sant’Antimo in 781 en route from Rome. On the occasion of his visit, he set his seal on the foundation of the monastery that was currently under construction. The monastery went through various renovations since then, but the structure visible today was largely intact in 1100 AD.

As you walk around both the exterior and interior of the church, notice all of the carvings of mythological animals and foliage on the capitals. These creatures and motifs are the result of Roman, Irish and Byzantine influence. Artists are said to have come from all over Europe to work on the church, and many of the capitals were the work of masters from the Lombard and French schools of sculpture and design. One of the most famous capitals is a sculpture of Daniel in the lion’s den located on the right side of the nave as you face the altar.

Abbazia di Monte Oliveto Maggiore

Do not miss the drive to Abbazia di Monte Oliveto Maggiore! It is an easy drive right through the Crete, the most dramatic and haunting landscape in all of Tuscany. The landscape is wild and timeless, with a majestic and austere beauty characterized by rolling green pastures that suddenly and dramatically collapse into a hostile landscape of deep and forbidding ravines. The fact that the Abbazia (or abbey) arises in solitary grandeur in the midst of this foreboding terrain is consistent with the founding order’s mission to live as hermits in renunciation of the world.

The approach to the Abbazia is up a beautiful, winding roadway surrounded by cypress trees leading to a parking lot near the entrance to the complex. Once you park, you walk up a drawbridge leading through a tower that originally served to defend the structure. There is a lovely Della Robbia terra-cotta of the Madonna and Child above the gate leading into the monastery. Once you enter the monastery, there is a walkway flanked by cypress trees that leads past an herbal garden, small chapels and a pool that originally served as a fishpond to the abbey’s main buildings, including the church, bookstore and cloisters.

The church, built between 1399 and 1417, was renovated in 1772 in an austere, late-Baroque style. The church is built in the shape of a Latin cross and houses magnificent inlaid wooden mosaics behind the choir that date from 1505. The real splendor of the Abbazia is the fifteenth-century cloister called the Great Cloister (Chiostro Grande) that was frescoed by Luca Signorelli from 1497 to 1498 and completed by Il Sodoma in 1502. The frescoes depict the life of St. Benedict in great detail, from the time of his youth when he left home to study in Rome to the culmination of his life as the founder and spiritual leader of a monastery.

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Three of our favorite restaurants in the Central Hilltop Towns region

Osteria Osticcio

This osteria and enoteca has everything you could want in Montalcino: thousands of bottles of wine, top-quality food and stunning views of the countryside.


Osteria Osticcio is located on Via Matteotti, which backs up to the edge of town. The back of the building is a glassed-in balcony where you are virtually hanging over the edge with fabulous, endless views of the surrounding countryside.

The food is Tuscan food at its best – simple but marvelously fresh. Consider a wine tasting to accompany your food. The osteria is known for its antipasti and  primi, including incredible cheese plates, fresh pasta, anchovies in pesto, bruschetta, prosciutto, salumi and bresaola.

Open for lunch and dinner every day except Thursday, when Osteria Osticcio is open for lunch only.

Address: Via Matteotti 23, Montalcino 53024

Ristorante Il Fornacino

This great restaurant is one of our favorites and much beloved for its excellent food, impeccable service and great ambiance.

This restaurant is not a tourist destination. It is off the beaten track but well worth the drive. Il Fornacino is not only a favorite of locals and Italian tourists but also of internationally renowned chefs. The dining room itself is lovely and casual – spotlessly clean and nicely decorated. However, the food is the real star of the show.

Specialties include homemade pasta, especially the pici with meat and porcini ragù and anything with truffles. The tagliata with truffles is a darling among foodies; it is thinly sliced beefsteak simply grilled with salt, pepper and olive oil and then topped with a generous portion of truffles. The house wine is also a winner and free flowing. Desserts too are wonderful but a personal favorite is the complimentary contucci (light, crisp, delectable) served with homemade Vin Santo.

Address: Via Gramsci 25/27, Guazzino 53048

Ristorante La Romita

La Romita is a tiny, five-table restaurant serving some of the best food in the area. La Romita is a husband-and-wife team with the wife, a Cordon Bleu chef, manning the kitchen and her husband taking over the front of the house.

La Romita has a highly specialized menu that changes with the seasons and the inventiveness of the chef. The restaurant offers an à la carte menu, but the prix fixe menu at 30 euros per person (exclusive of wine) is the best value and a chance to sample a variety of courses.

The dining room is intimate and cozy, with beautiful frescoed walls. The outside garden terrace is delightful for dining alfresco, especially on warm summer nights when there is a splendid view of the moon rising over the hills in the distance.

La Romita is slow food at its best. The service is friendly and thoughtful, the food is superb and perfectly paired with Tuscan wine and the location overlooking the Tuscan countryside is about as good as it gets.

Address: Via Umberto I 144, Montisi 53020

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Three of our favorite places to stay in the Central Hilltop Towns region

Locanda Vesuna

Locanda Vesuna is located in the beautiful Val d’Orcia countryside just north of Pienza, situated on top of a hill with a splendid vista of olive trees, wheat fields and Monte Amiata. At night the twinkling lights of hilltop towns in the distance are a splendid and peaceful sight.

The hotel consists of one large stone building with a splendid courtyard in the middle. The view from the courtyard is picture-perfect, revealing a dreamlike Tuscan fantasy. The property has four suites, four double rooms and a comfortable apartment with three rooms, a kitchen and a spacious living room with a fireplace.

The property also has an amazing pool. It is large and set on the horizon, with beautiful and panoramic views. More importantly, though, the pool uses a chemical-free ionization system to keep the water incredibly fresh and clear without the smell and harsh effects of chlorine. There is also a hot tub, where you can enjoy a nice glass of wine while gazing at a star-filled sky or the distant twinkling lights of neighboring medieval villages.

Run by an extremely competent and friendly staff, Locanda Vesuna is a jewel of a place with a central location close to Pienza and very convenient to all locations in central Tuscany.

Address: Podere Pecorile Vecchio 19, Località St. Ambrogio, Trequanda 53020

Il Canto del Sole

l Canto del Sole is a wonderful bed and breakfast located in the beautiful, open terrain of the Crete Senesi. Its name, which means “Song of the Sun,” is very poetic and consistent with the beauty and spirit of this place.

Il Canto del Sole is comprised of two adjacent buildings: Il Canto del Sole and Il Podere Casino. Il Canto del Sole is a barn that has been converted into two air-conditioned two-bedroom apartments fully furnished with a bathroom and kitchenette. Il Podere Casino is an eighteenth-century Tuscan farmhouse that has been lovingly restored and converted into six guest rooms that are very light, airy and decorated with simple antique furniture from the original farmhouse.

The owners, Luciano and Laura, are some of the most gracious hosts in Tuscany. They provide a high level of service and appear to work tirelessly to provide their guests with a wonderful experience.

Address: Via di Villa Canina 1292, Località Cuna, Monteroni d’Arbia 53014


L’Olmo is a luxurious country estate located in the beautiful rolling farm country just southeast of Pienza, near Monticchiello. This charming boutique hotel is meticulously maintained, with gorgeous grounds and elegant, spacious suites. Originally a sixteenth-century stone manor, L’Olmo has been converted into a refined and stylish hotel. The owner provides warm and thoughtful service, making for a memorable stay.

The suites feature beautiful wood-beam ceilings, luxurious Italian fabrics, antique chests, extremely comfortable beds and pillows, and amazing travertine marble bathrooms. The rooms also have private outside entries, making L’Olmo a good place for a romantic getaway.

Address: Località Monticchiello, Pienza 53026


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One of our favorite wineries in the Central Hilltop Towns region

Poggio Antico

Poggio Antico, a family-owned winery, is located in the hallowed ground south of Montalcino. A drive down to the winery and then through the long, cypress lined avenue to the winery is one of life’s great pleasures. Poggio Antico offers an intimate and informative tour to small groups of people. The tour is followed by a tasting in the winery’s charming enoteca.

The best way to tour Poggio Antico is to schedule the tour late in the day and follow the tour with dinner at the widely acclaimed Ristorante di Poggio Antico. This fine restaurant is on-site, and you can bring one of your recently purchased bottles of Poggio Antico’s wine to the restaurant and enjoy it with your meal. There is no corkage fee, so what better way to taste and enjoy Poggio Antico’s splendid wine?

Poggio Antico produces some of the finest Brunello wine available and has received many accolades through the years. In 1985, its Brunello was declared number four in  Wine Spectator’s Top 100 Wines of the Year (the first Italian wine to achieve this ranking!). Since then, Poggio Antico’s wines have been included on the list six more times and continue to occupy the very top rankings of Brunello. This success derives from the estate’s extraordinary terroir, an almost perfect combination of geography, geology and climate. The tour is as satisfactory as the wine itself.

Address: Località Molinello, Montalcino 53024

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