Wander your way through Italy's idyllic countryside, walking and hiking on ancient footpaths, sampling its finest food and wine along with its rural pace and way of life.

The landscape of neighboring Tuscany and Umbria is soul-stirring, with its sweeping vistas of vineyard-cloaked hills and stately cypress trees ringing storied hill towns. The scenery is rich in natural beauty, and reminiscent of early civilizations. Distinguished by its fascinating history, the region is noted for its unique culture and architecture. This is a place where the union of art and nature has been celebrated for thousands of years. This favorite Italy walking tour takes us across the vibrant countryside, down ancient footpaths, across fertile valleys, and through picturesque towns. Tuscany and Umbria is a land of bountiful harvests and flavors, and our journey becomes as much a culinary and Italian wine tour as it is a walking tour. At day's end, we relax in the region's most charming hotels and savor hearty Tuscan cuisine that is complemented by memorable local wines.

Days 1-2: Meet for a walking tour of Siena, Italy, a walled city of fascinating Gothic architecture. Transfer to the lovely town of Scansano, in the heart of Tuscany's Maremma region. Explore ancient Etruscan sites and beautiful coastline, in a region that is home to Italian cowboys.

Days 3-4: Transfer to the hill town of Montalcino. Indulge in tasting one of Italy's best red wines, the famous Brunello. A short drive brings us to Montepulciano, where we begin a walk through idyllic countryside to the tiny Renaissance village of Pienza.

Days 5-7: In the hilltop village of Spello, explore the walled village with signs of its Roman, Gothic, and Renaissance splendor unveiled through its narrow cobblestone streets. Hike through the Natural Park of Mount Subasio. Enjoy a tasting of fine local wines. Dine on the culinary specialties of Umbria, a region of distinctive styles and flavors.

Day 8: Visit Assisi, the enclosed city of basilicas, Roman temples, and castles. Transfer to Foligno for connecting trains, or to Florence, and say arrivederci.

Italy is a country meant to be savored. Our eight-day Italy walking and hiking tour through the rich regions of Tuscany and Umbria allows sufficient time, and moves at the proper relaxed pace, to experience all that is Italian - scenic countryside, fresh gourmet picnics, exceptional Brunello wines, and luxurious accommodations. If the Italians don't settle for anything but the finest, why should we?

Most Convenient Airports:
Rome (airport code FCO); or Florence (airport code FLR)

Meeting Time and Place:
1:00 p.m. in front of the Jolly Hotel Excelsior, Piazza La Lizza 1, Siena

Departure Time and Place:
Your guides will provide transportation to the Foligno train station by 2:30 p.m., and from there it is easy to catch trains to other cities in Italy.

Overview: First-class and charming accommodations in ideal locations with beautiful views.

Nights 1 & 2: 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.

Nights 3 & 4: Hotel Dei Capitani
Montalcino, Italy

A small, charming hotel on the edge of Montalcino’s medieval walls with stunning views of the Orcia Valley.

Nights 5, 6, & 7: Hotel la Bastiglia
Spello, Italy

Located on the slope of Mount Subasio, in the walled medieval town of Spello, this small, elegant hotel offers beautiful views over the Umbrian countryside and an excellent restaurant.

DAY 1 
Siena to Montemerano

Walking – easy, 2-4 hours on pedestrian streets.

We meet in the historic center of Siena, and our exploration of Italy begins with a walking tour through the quiet pedestrian streets of this fascinating city. Siena is a fabulous place to stroll and offers some of the most important examples of medieval architecture in existence. Founded by the Etruscans, Siena later became a Roman colony and flourished during the 13th and 14th centuries. Siena’s architecture is a glorious mix of Gothic and Romanesque elements. Our visit includes the semicircular Campo, the 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 Etruscan history. Here we see 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.
Relais Villa Acquaviva, Montemerano, Italy

DAY 2
Uccellina Nature Reserve

Walking – easy to moderate, 3-5 hours along country roads and trails.

After breakfast, we head for the glorious Maremma coast, one of the last undeveloped stretches in Italy. A day of walking in this beautiful nature reserve brings us along a dramatic coastline characterized by the Uccellina Mountains, which reach over 1,500’, and by expansive beaches and steep cliffs. Here, isolated Sienese watchtowers, built in the 15th century to keep lookout for marauding pirates, rise above pine forests and farmlands.

The park is an expanse of land encompassing beach, pine forest, marshes, canals, mountains, and farmland. Vegetation includes the Mediterranean macchia, juniper, heather, rock-rose, holm oak, dwarf fan palm, and centuries-old olive groves. We may be fortunate enough to spot any number of fauna including wild boar, roe deer, fox, porcupine, badger, and fallow deer. Unique to this area is the co-existence of wildlife with semi-domesticated species such as Maremman cattle and horses. Bird life includes cormorants, little egrets, blue herons, and wild ducks. No trip to the Maremma is complete without a glimpse into the life of the Maremman buttero. The buttero is to Maremma what the cowboy was to the wild west and the gaucho was to Argentina. On this day we enjoy a picnic lunch, either among the dunes on the beach or sitting beside one of the ancient watchtowers.

In the late afternoon we return to our villa where we can relax with cocktails on the terrace. We enjoy dinner this evening at a very special restaurant in the heart of Montemerano.
Relais Villa Acquaviva, Montemerano, Italy

DAY 3 
Pitigliano to Sovana; transfer to Montalcino

Walking – easy to moderate, 3-5 hours along country roads and trails.

Today’s walking route leads us between the extraordinary hill towns of Pitigliano and Sovana, 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 Etruscancivilization, were heavily influenced by their culture.

We begin our journey in 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 synagogue has been lovingly restored and the important role the Jewish community had in the town’s history has been kept alive. We take time to visit the synagogue and wander through the narrow streets of this antique ghetto before departing on foot to Sovana.

Once outside of Pitigliano, our footpath follows ancient routes along wooded trails dotted with ruins of Etruscan tombs. We cross small streams via Roman bridges and finally reach the charming 7th-century village of Sovana. We take time to explore the history and architecture of this small wonder, and you are free to have lunch on your own.

Following lunch in Sovana, we transfer to Montalcino, a small, sleepy, but well-to-do hill town that has changed little since the 16th century. Our hotel offers exceptional vistas over faded terra-cotta roof tiles, and a timeless landscape covered with vineyards of the Sangiovese Grosso grapes. Montalcino is one of Italy’s most important wine towns, famous for fine Brunello wines, arguably Italy’s most distinguished.

This evening we celebrate la dolce vita in high style as we dine at one of the finer restaurants in Tuscany. The “Tavern of the Castle” as it is referred to, is a converted ancient mill located next to a 14th-century church, surrounded by vineyards in beautiful countryside. Here we are treated to many Tuscan delicacies as well as a sampling of the fine wines from the region.
Hotel Dei Capitani, Montalcino, Italy

DAY 4 
Montalcino to the Abbey of Sant’Antimo

Walking – easy to moderate, 3-4 hours along country roads and trails.

This morning our walking route brings us from Montalcino to the Abbey of Sant’Antimo, perhaps the largest and finest example of Romanesque architecture in Tuscany. From Montalcino we walk along what was once a Roman road through vineyards, farmlands, olive groves, and small hamlets. The surroundings are beautiful and wildflowers line the path. The road we walk is part of the famed Camino de Santiago pilgrimage route linking Rome to Santiago de Compostela in Spain. According to legend, the lovely Abbey of Sant’Antimo was founded in the 9th century by Charlemagne when a local herbalist miraculously cured his troops of an illness. We arrive in time to hear the soft sound of the monks’ Gregorian chants, which evoke a sense of history and mystery that transports us back to the Middle Ages.

Following lunch in a local osteria, or perhaps a picnic in a sunny field, we return to Montalcino. The afternoon is free to explore this charming village, or set out on an afternoon walk through the surrounding vineyards. Tonight for dinner you are free to explore one of the many lively trattorias only a short walk from our hotel.
Hotel Dei Capitani, Montalcino, Italy

DAY 5 
Montepulciano to Pienza; transfer to Spello

Walking – easy to moderate, 4-5 hours along country roads and trails.

Our exploration today begins in Montepulciano, the highest of the Tuscan hill towns. Montepulciano is built along a narrow ridge southeast of Siena and the town is encircled by walls and fortifications designed by Antonio da Sangallo the Elder in 1511. Inside the walls, the streets are lined with Renaissance-style buildings and churches. The town is chiefly known for its much-celebrated local wine, Vino Nobile. Montepulciano is set in a superb walking region, and our route into magnificent wine country passes through the small medieval walled village of Monticchiello, where we stop for lunch and perhaps a gelato. Monticchiello provides a charming place to break, with its narrow streets and small squares.

For those who wish to continue walking, it is another two hours to reach Pienza on foot, or our van awaits for anyone who wishes to ride. Our afternoon of walking continues through the countryside and concludes in the main square of the medieval town of Pienza, built in the 1300’s by Pope Pius II. Pienza is the only town center in Italy to have survived the centuries almost perfectly intact, and it is considered one of Tuscany’s Renaissance gems. 

This afternoon we say good-bye 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. This is a land of flavors and tastes, and Umbrian cuisine is simple but delicious and 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, in a charming hotel with magnificent views of the wide valley below. Upon arrival, our guides provide a short exploration and overview of the town of Spello. A walk through Spello is a feast for the eyes, as cobblestone passageways open into intimate closed piazzettas, and lead to Roman arches and Romanesque churches.

Our day ends in a medieval wine cellar for a tasting of Umbria’s fine local vintages, prize-winning olive oils, and various Umbrian delicacies. This evening we enjoy more Umbrian specialties at a local restaurant.
La Bastiglia, Spello, Italy

DAY 6 
Assisi to Spello

Walking – easy to moderate, or moderately strenuous option, 4-6 hours along country roads and trails.

A short drive this morning brings us through Assisi, justly acclaimed as the “crown jewel of the medieval hill towns” and up to the Natural Park of Monte Subasio for a return walk to Spello. Our walk, one of the most beautiful in Umbria, winds through olive groves and ancient oak and chestnut trees, traverses the farmed lower slopes of Monte Subasio, and offers astonishing views across Umbria to the hills of Tuscany.

Following lunch, our route descends along forested trails, past herds of sheep, and through local villages. We pass through the small, picturesque village of Colle Pino, where we stop to relax for a refreshment and to absorb some of the local culture around the town square. Our final descent brings us through the farmland surrounding Spello, and we make a triumphant return as we pass through the gates of this walled city and return to our hotel. You are free to continue your exploration of Spello as dinner this evening is on your own.
La Bastiglia, Spello, Italy

DAY 7
Gubbio

Walking – easy to moderate, 3-5 hours along country roads and trails.

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, proud mountain outpost has retained its medieval charm and authentic flavor. The austere grandeur of the often photographed central square, the Piazza Grande, makes it hard to imagine the harsh atmosphere of medieval life.

We begin the day with an exploration of this ancient town, founded by the Etruscans and conquered by the Romans. Gubbio is rich in monuments, testament to its glorious past, and a wonderful walk with stunning views awaits us in the hills behind the city. We walk by grazing herds, watchtowers, and ancient castle remains, and through hills of intense green that, in spring, are lightened by the yellow of scotch broom bushes.

Upon returning to Spello, the outdoor terrace of our hotel beckons us for an apertivo prior to this evening’s farewell dinner at our hotel’s excellent restaurant.
La Bastiglia, Spello, Italy

DAY 8 
Assisi

Walking – easy, 1-2 hours on quiet city streets.

This morning we delve deeper into the heart of Assisi, a town imbued with the mystical spirit of one of the most fascinating figures of Western religious history, St. Francis. Even without St. Francis, Assisi would be irresistible – a charming town nestled under the forested peak of Monte Subasio. However, the monuments that have been dedicated to the saint make Assisi a highlight of any visit to Umbria.

We visit the upper and lower churches of the Basilica, built in the 13th century to house the body of St. Francis of Assisi, patron saint of Italy and most beloved of all saints for the Italians. The greatest masters of the time – Cimabue, Giotto, Simone Martini, Pietro Lorenzetti – were called here to create frescos, rendering this church one of Italy's most outstanding art museums. We also visit the Roman Tempio di Minerva, the city hall on the Piazza del Comune, Assisi’s main piazza, and the Gothic church of St. Chiara. We continue to the Rocca, an old fortress dominating the town and the valley below.

Following our exploration of the great spiritual and artistic treasures of Assisi, a short drive brings us to Foligno where you may make the short train connections to Rome, or other destinations throughout Italy.

Please note that this is a typical itinerary, and actual activities may vary to take advantage of weather conditions, local events, and to allow serendipity to play a hand in your experience. Accommodations are as outlined in the itinerary, although we reserve the right to change these should the need arise.
 

$4,495 per person

• Expert leadership
• All accommodations
• All meals except one lunch and two dinners
• All activities as noted in the itinerary