Italy’s Idyllic Countryside with Boundless Journeys

This morning we meet in Florence and transfer to Siena. After a welcome lunch of Sienese specialties, our exploration of Italy begins with a walking tour through the vibrant pedestrian streets of this fascinating city. Siena preserves its medieval character beautifully with a mix of Gothic and Romanesque elements. Founded by the Etruscans, Siena later became a Roman colony and flourished during the 13th and 14th centuries. Our visit includes the semicircular Campo, a public square famous for the annual Palio horse race and the focus of Sienese life since 1340, as well as the impressive Duomo Cathedral.

From Siena our journey leads us into the Maremma region, an area known as the "wild west" of Tuscany, with wide rolling hills, golden wheat fields, and rich with Etruscan history. In this off-the-beaten-path region, we may come across Italian cowboys in fedoras riding sturdy horses and herding long-horned Maremmano bulls.
Our home for the next two nights is an elegant villa surrounded by vineyards and olive groves, offering stunning views of the Maremma countryside. We are welcomed with a wine tasting in the Enoteca, an old cellar inside the villa, where vintage wine is maturing in oak barrels.

This evening's dinner is in the medieval town of Montemerano. After a stroll through the alleys and the central square, with its romantic charm, we dine in an ancient olive oil mill transformed into a delightful Tuscan restaurant.

Accommodations

Relais Villa Acquaviva
Montemerano-Saturnia, Italy

A converted villa of former Italian nobility, surrounded by vineyards and olive groves, Relais Villa Acquaviva offers stunning views of the Maremma countryside. Amenities include a wine cellar, restaurant and bar, and an outdoor swimming pool.

Today we explore the extraordinary hill towns of Sovana and Pitigliano, each rich in Etruscan remains. The Etruscans were mysterious people that settled the Italian peninsula sometime between 800 and 900 BC. The Romans, who were only villagers during the rise of the Etruscan civilization, were heavily influenced by their culture.

Our day begins in the 7th-century village of Sovana. The sand-colored streets, battle-worn but effortlessly characteristic buildings, and unassuming old center are honest and simply beautiful. From here, we continue to the neighboring town of Pitigliano, once one of the most densely Jewish-populated towns in Italy. After fleeing Rome in the 15th century, many Jewish families formed a community in this Maremma town, which became known as "Little Jerusalem." While only a few Jewish families remain in Pitigliano today, the important role the community had in the town's history has been kept alive. We enjoy lunch in one of the more noted restaurants in town, savoring locally produced white wine.

After returning to our hotel in the late afternoon, we head to Manciano. Here we enjoy a cooking class of Tuscan specialties at La Filanda, situated on the outskirts of the old village. Preference is given to Tuscan products such as Cinta Senese pork and Maremmana meats, handmade pasta, ewe's milk, and goat cheeses. After immersing ourselves in the kitchen, we enjoy the fruits of our labor as we dine on our creations.

Accommodations

Relais Villa Acquaviva
Montemerano-Saturnia, Italy

A converted villa of former Italian nobility, surrounded by vineyards and olive groves, Relais Villa Acquaviva offers stunning views of the Maremma countryside. Amenities include a wine cellar, restaurant and bar, and an outdoor swimming pool.

This morning's hike from the small village of San Quirico di Sorano winds along a track through Etruscan vie cave, roads carved through volcanic tuff more than 2,000 years ago, to the rupestrian settlement of Vitozza. Inhabited from the 12th to the 18th century, this complex is composed of approximately 180 grottos entirely dug out of the rocky bank on which they stand. After exploring this extensive settlement, we continue our walk down to the valley of the Lente River, where we pass through woodlands to the town of Sorano. Entering through the lower gate, or Porta dei Merli, we explore the charming medieval center, and walk through a maze of characteristic side streets up to the Masso Leopoldino—a fortress built in the 18th century offering stunning views over Sorano and the surrounding river valley.

Midday, we enjoy lunch in a local family-run trattoria before continuing our hike across the Lente River and up the far side of the gorge—following one of the best preserved vie cave in the area (Via Cava di San Rocco). The narrow road, with steep rock faces on both sides, winds its way through volcanic rock, hidden by lush vegetation, to a natural balcony with spectacular views. Located here is the smaller rupestrian settlement of San Rocco where we find a number of caves dug along the cliffs overlooking Sorano.

This afternoon we transfer to our new home for two nights, in the village of San Quirico d'Orcia. Of ancient origin, San Quirico owes its development in the Middle Ages to its excellent position on the Via Francigena, which crossed the hamlet from one end to the other, flanked by churches, hospitals, taverns, shops and workshops. The impressive Collegiate church dates to the 13th century, decorated with artwork attributed to Giovanni Pisano.

Tonight we celebrate la dolce vita, as we are treated to a dinner of Tuscan delicacies, such as Florentine steak, tiramisu, and panna cotta, as well as a sampling of fine wines from the region.

Accommodations

Palazzo Del Capitano Wellness & Relais
San Quirico d’Orcia, Italy

Located just inside San Quirico d’ Orcia’s historic town walls, Palazzo del Capitano is set in a charming 15th-century building surrounded by olive groves and Mediterranean gardens. The wellness center is available on reservation and includes a hot tub, a Turkish bath, and massage services. Rooms are decorated in a rustic style, with wooden-beamed ceilings, antique furniture and terracotta floors. The Michelin-recommended Vecchio Forno restaurant serves Tuscan food indoors by the fireplace, or outside under the olive trees.

We begin today's excursion by foot, as we depart from the hotel and walk a portion of the Via Francigena, part of the pilgrimage route linking Canterbury to Rome. We pass by the ancient Castle Hamlet of Vignoni, eventually arriving to the small town of Bagno Vignoni, well known for its curative thermal waters. Discovered in Roman times, it wasn't until the Middle Ages that the small village developed around the ancient thermal structure. These baths were well enjoyed by Popes and Nobility, who came here to "take the waters."

After wandering the village, we can soak our feet in the natural warm water ravine, before lunch at a 16th-century farmstead. Here we are treated to a tasting of pecorino cheese, salt-cured meats, as well as homemade jams and olive oil. From this family-run agriturismo, our afternoon walk begins, along on a countryside dirt road affording picture perfect vistas of the Orcia Valley, with ancient farmhouses, wheat fields, and grazing sheep.

Before returning to the hotel, we stop in the town of Pienza, originally called "Corsignano." A UNESCO World Heritage Site since 1996, Pienza is one of the towns in Italy to have survived the centuries almost perfectly intact, since it was rebuilt by Pope Pius II as a planned Renaissance town

We take time to stroll the streets of the village and perhaps enjoy a caffe or browse in some of the quaint shops. Upon returning to San Quirico in the late afternoon, you are free to dine at one of the many lively trattorias in town, or the well-known restaurant at our hotel.

Accommodations

Palazzo Del Capitano Wellness & Relais
San Quirico d’Orcia, Italy

Located just inside San Quirico d’ Orcia’s historic town walls, Palazzo del Capitano is set in a charming 15th-century building surrounded by olive groves and Mediterranean gardens. The wellness center is available on reservation and includes a hot tub, a Turkish bath, and massage services. Rooms are decorated in a rustic style, with wooden-beamed ceilings, antique furniture and terracotta floors. The Michelin-recommended Vecchio Forno restaurant serves Tuscan food indoors by the fireplace, or outside under the olive trees.

This morning our walking route brings us from fortified Medieval town of Montalcino, home of the great Tuscan red wine, to the Abbey of Sant'Antimo, perhaps one of the best examples of Romanesque architecture in Tuscany. According to legend, the Abbey of Sant'Antimo was founded in the 9th century by Charlemagne when a local herbalist miraculously cured his troops of an illness.

From Montalcino, we walk along a trail through vineyards, farmland, olive groves, and small hamlets. In the springtime wild broom line the path, and in the autumn plum grapes ready for harvest will tempt us from the vines.

After lunch at a nearby restaurant, we say goodbye to Tuscany and head south into Umbria, the "Green Heart of Italy." Umbria is rich in natural treasures, but also in great and ancient civilizations. It is a land whose rolling hills are dotted with castles, fortresses, and watchtowers, and whose valleys are laced with countless gleaming rivers and splashed with colorful wildflowers. Umbrian cuisine is simple but delicious, based on locally-grown ingredients perfected over the centuries. Our home for the next three nights is the Roman and medieval hill town of Spello. A walk through town is a feast for the eyes, as cobblestone passageways open into intimate piazzettas, and lead to Roman arches and Romanesque churches. This evening we enjoy a grand welcome in Umbria with a special dinner prepared in an upscale local restaurant.

Accommodations

La Bastiglia
Spello, Italy

La Bastiglia is set in a peaceful and panoramic location in the historical center of the medieval village of Spello, just 3 miles from Assisi. Housed in a magnificent 17th-century building, this charming hotel features a number of interesting works of art. Amenities include a wellness center, outdoor swimming pool, and one of the best known restaurants in the area. Spacious and comfortable guest rooms feature spectacular views.

A short drive from Spello brings us to Gubbio, a remote part of Umbria dramatically perched on a hill overlooking the ruins of its Roman theater. This classically picturesque and proud mountain outpost has retained its medieval charm and authentic flavor. The austere grandeur of the much photographed central square, the Piazza Grande, makes it hard to imagine the harsh atmosphere of medieval life.

Today's walk begins on the outskirts of town. We follow an old cart track which leads us through a small ravine to an isolated country shrine. Our walk continues uphill slowly, arriving eventually at the Sanctuary of Saint Ubaldo. After visiting this venerated place, and learning more about the Corsa dei Ceri - the famous "Candle Race" which has been run uninterrupted every May 15th since the 12th century—we take a funicular ride down to the center of town, where we enjoy lunch in a traditional restaurant.

In the afternoon, we head back towards Assisi for a guided visit of the Basilica of Saint Francis. The upper and lower churches of the Basilica were built in the 13th century to house the body of St. Francis, patron saint of Italy and the most beloved of all saints for the Italians. The greatest masters of the time—Cimabue, Giotto, Simone Martini, and Pietro Lorenzetti—were called here to create frescos, rendering this church one of Italy's most outstanding art museums.

This evening you are free to continue your exploration of Spello, as dinner is on your own.

Accommodations

La Bastiglia
Spello, Italy

La Bastiglia is set in a peaceful and panoramic location in the historical center of the medieval village of Spello, just 3 miles from Assisi. Housed in a magnificent 17th-century building, this charming hotel features a number of interesting works of art. Amenities include a wellness center, outdoor swimming pool, and one of the best known restaurants in the area. Spacious and comfortable guest rooms feature spectacular views.

A short drive this morning brings us to the natural park of Monte Subasio for a return walk to Spello. Our trail, one of the most beautiful in Umbria, winds through olive groves and ancient oak and chestnut trees, traversing the cultivated lower slopes of Monte Subasio, with astonishing views across Umbria to the hills of Tuscany. Our route descends along forested trails and up through open pastures, where we may pass grazing horses, sheep, and cattle.

Eventually, we come upon the small, picturesque village of Collepino, where we stop for lunch. Our final descent follows the aqueduct that brought water to the town from the mountain during the Roman Empire, and we make a triumphant entrance as we pass through the gates of this walled city and return to our hotel.

Upon our return to Spello, the outdoor terrace of our hotel beckons us for an apertivo prior to a final celebratory dinner at La Bastiglia's acclaimed restaurant.

Accommodations

La Bastiglia
Spello, Italy

La Bastiglia is set in a peaceful and panoramic location in the historical center of the medieval village of Spello, just 3 miles from Assisi. Housed in a magnificent 17th-century building, this charming hotel features a number of interesting works of art. Amenities include a wellness center, outdoor swimming pool, and one of the best known restaurants in the area. Spacious and comfortable guest rooms feature spectacular views.

Today we continue to explore the great spiritual and artistic treasures of Assisi. Its narrow and steep lanes are picturesque and reveal plenty of surprises: a hidden restaurant, a faded fresco, a stunning view. Occasional olive trees are spotted among the stairways and rooftops, where shy cats creep out of sight of passers-by.

There are many interesting buildings along the main street, including the 12th-century Romanesque facade of the Cathedral of San Rufino, and the town's art gallery, the Pinacoteca Comunale. We visit the Basilica di Santa Chiara, the Temple of Minerva, and the city hall on the Piazza del Comune, Assisi's main piazza.

For the best view of the town, we continue to Rocca Maggiore, a large fortress towering above Assisi. In addition to the town itself, there are spectacular views of the surrounding plains, hills, and valleys.

Following our tour of Assisi, you will have time to enjoy lunch in town before a short drive to the train station. From here you can make train connections to Rome, or other destinations throughout Italy, to catch flights home.