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HIGHLIGHTS
A quick look about this trip!
DURATION
8 DAYS
COMFORT
LANGUAGE
RATING
  • Daily walks through beautiful landscapes with vineyards, olive groves, cypress trees, and ancient hill towns
  • Visits to the medieval towns of Montalcino, Pienza, Assisi, and Spello
  • Coastal Maremma region of Tuscany, with its Etruscan sites and Italian cowboys
  • Tuscan cooking class, wine and cheese tastings, and fine accommodations
ACTIVITIES ON THIS TRIP
Primary: Local Culture & Cuisine, Walking Tour
Other: wine tasting, cooking, Local Food
$4495USD
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ITALY: A Taste of Tuscany & Umbria

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. 

DAY 1: Meet in Florence; transfer to Siena and Montemerano.
Walk – easy, 2-4 hours on pedestrian streets.

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 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 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, the old cellar inside the villa, where vintage wine is maturing in oak barrels.

This evening dinner is in the medieval town of Montemerano. After a stroll through the alleys and the central square with its solemn and romantic charm, we dine in an ancient olive oil mill transformed into a delightful Tuscan restaurant. 
Lodging Relais Villa Acquaviva, Montemerano
Description Stay on a typical Tuscan wine estate at Relais Villa Acquaviva, located 800m from Montemarano’s pretty medieval centre. Well-located for exploring the Maremma, this country house offers great facilities. Relax in peaceful rooms surrounded by 15 hectares of vineyards which produce some of the area’s best wines, from Bianco di Pitigliano to Morellino di Scansano. Taste the Acquaviva’s own wine and oil in the Relais’ wine cellar. Relais Acquaviva’s rooms are decorated in a rustic, Tuscan style. Some rooms come with hot tubs or panoramic terraces.
DAY 2: Uccellina Nature Reserve; transfer to Montalcino
Walk – easy to moderate, 3-5 hours along country roads and trails (approximately 7 miles).

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. On this day we enjoy a picnic lunch, either among the dunes on the beach or sitting beside one of the ancient watchtowers.

This evening we enjoy a cooking class of Tuscan specialties at La Filanda, situated in the old walls of Manciano. Preference is given to Tuscan products, such as cinta senese pork products and maremmana meats, handmade pasta, ewe’s milk, and goat’s cheeses. After immersing ourselves in the kitchen, we enjoy the fruits of our labor as we dine on our creations.
Lodging Relais Villa Acquaviva, Montemerano
Description Stay on a typical Tuscan wine estate at Relais Villa Acquaviva, located 800m from Montemarano’s pretty medieval centre. Well-located for exploring the Maremma, this country house offers great facilities. Relax in peaceful rooms surrounded by 15 hectares of vineyards which produce some of the area’s best wines, from Bianco di Pitigliano to Morellino di Scansano. Taste the Acquaviva’s own wine and oil in the Relais’ wine cellar. Relais Acquaviva’s rooms are decorated in a rustic, Tuscan style. Some rooms come with hot tubs or panoramic terraces.
DAY 3: Etruscan trails of Pitigliano and Sovana; Transfer to Pienza
Walk – easy to moderate, 3-5 hours along country roads and trails (approximately 5 miles).

Today we explore 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 Etruscan civilization, were heavily influenced by their culture.

Today’s walk to Pitigliano takes us through a beautiful landscape of hills, vineyards, farms, and wooded paths, ending at the stunning Vie Cave, presumably Etruscan roads carved by hand through volcanic rocks more than 2000 years ago.

Upon arrival we explore the town, 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 Jewish community had in the town’s history has been kept alive. After lunch and possibly some of the excellent white wine produced in this town, we continue to the charming 7th-century village of Sovana, taking time to explore the history and architecture of this small wonder.

Later today we transfer to Pienza, originally called Corsignano. Pope Pius II had the entire village rebuilt as the first-ever planned Renaissance town. A UNESCO World Heritage Site since 1996, Pienza is the only town center in Italy to have survived the centuries almost perfectly intact.

This evening we celebrate la dolce vita in high style as we dine at one of the finer restaurants in Tuscany, Re di Macchia. After a walk through the charming streets of Montalcino, we are treated to a dinner of Tuscan delicacies, such as Florentine steak, tiramisu, and panna cotta, as well as a sampling of the fine wines from the region.
Lodging Hotel Corsignano, Pienza
Description The Corsignano is in Pienza and offers breathtaking views of the Orcia Valley. This family-run hotel offers a terrace with jacuzzi, and a typical Tuscan restaurant. Hotel Corsignano features spacious rooms and junior suites, some offering a private balcony overlooking the valley. Free Wi-Fi is available throughout the hotel.
DAY 4: Sant’Anna in Camprena
Walk – easy to moderate, 3-4 hours along country roads and trails(approximately 5 miles in the morning, 1 mile in the afternoon).

Today’s walk along olive groves and wheat fields affords us breathtaking views of the Orcia Valley and the Crete Senesi (Sienese hills). Our destination is the 15th-century convent of Sant’Anna in Camprena, a former Olivetan Benedictine monastery where the English Patient was filmed. The monks’ refectory houses five large landscape paintings by Sodoma, inspired by the hills of Tuscany and Umbria.

Lunch today is at a 16th-century farmstead where we are treated to a tasting of pecorino cheese, as well as homemade jams and olive oil.

The afternoon is free to explore Pienza. You can walk the streets and take in the sights and smells of this town, famous for the pecorino cheese we enjoyed earlier today, or perhaps you will choose to take an optional outing to soak in the Thermal baths at Bagno Vignoni (at an additional expense).

Tonight for dinner you are free to explore one of the many lively trattorias only a short walk from our hotel. 
Lodging Hotel Corsignano, Pienza
Description The Corsignano is in Pienza and offers breathtaking views of the Orcia Valley. This family-run hotel offers a terrace with jacuzzi, and a typical Tuscan restaurant. Hotel Corsignano features spacious rooms and junior suites, some offering a private balcony overlooking the valley. Free Wi-Fi is available throughout the hotel.
Day 5: Pienza to the Abbey of Sant’Antimo
Walk – easy to moderate, 3-4 hours along country roads and trails (5 miles).

This morning our walking route brings us from Pienza 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 pilgrimage route linking Canterbury to Rome. 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.

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. This is a land of flavors and tastes; 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 guide provides a short overview of the town’s history. 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.

This evening we enjoy a grand welcome to Umbria with dinner prepared by chef Marco Gubbiotti at our hotel restaurant. 
Lodging La Bastiglia, Spello
Description La Bastiglia restaurant hotel in Spello is mentioned among the most important gastronomic and hotel guides (one star in the Michelin Guide).
DAY 6: Gubbio
Walk – easy to moderate, 3-5 hours along country roads and trails (approximately 5 miles).

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 often photographed central square, the Piazza Grande, makes it hard to imagine the harsh atmosphere of medieval life.

We begin the day with a wonderful walk through this ancient town, founded by the Etruscans and conquered by the Romans, with a walk through its piazzas, churches, public palace, and ceramic shop, which carries on the tradition of the great renaissance artist Mastro Giorgio.

We continue with a funicular ride to the wooded paths and 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. Along the way, we stop for lunch in this picturesque setting.

This afternoon we visit the Basilica of Saint Francis in Assisi. We visit the upper and lower churches of the Basilica, built in the 13th century to house the body of St. Francis, 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. 

This evening you are free to continue your exploration of Spello as dinner is on your own.
Lodging La Bastiglia, Spello
Description La Bastiglia restaurant hotel in Spello is mentioned among the most important gastronomic and hotel guides (one star in the Michelin Guide).
DAY 7: Monte Subasio
Walk – easy to moderate, or moderately strenuous option, 4-6 hours along country roads and trails (approximately 8 miles).

A short drive this morning brings us 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 Collepino, where we stop to relax for a refreshment and to absorb some of the local culture around the town square. Our final descent follows the Roman 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 a nearby exclusive restaurant. 
Lodging La Bastiglia, Spello
Description La Bastiglia restaurant hotel in Spello is mentioned among the most important gastronomic and hotel guides (one star in the Michelin Guide).
DAY 8: Assisi; Departure from Foligno
Walk – easy, 1-2 hours on city streets.

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

There are many interesting buildings along the main street, the 12th-century Romanesque facade of the Cathedral of San Rufino, and the town’s art gallery, the Pinacoteca Comunale. We will 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 over the town, we continue to Rocca Maggiore, the large fortress towering above Assisi. As well as of the town itself, there are spectacular views over 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 Foligno train station. From here you can make train connections to Rome, or other destinations throughout Italy, to catch flights home.

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.
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Diane Cook
When I planned to take a walking trip to Italy I knew I wanted to feel it as much as see it. I was hoping to eat good food, drink great wine, and then hike off all those calories. I did just that, while getting vast knowledge about the art, grapes, and architecture. Our guides Alex and Christopher are an asset to your company. We all agree it exceeded our expectations. I have begun my own ‘Boundless Journey'.
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TRIP INCLUDES
  • Expert leadership
  • All accommodations
  • Wine and cheese tastings
  • Tuscan cooking class
  • All meals except one lunch and two dinners
CANCELLATIONS: 20% cancellation fee applied if cancelled 60 days prior to departure. Cancellations within 60 days are 100% non-cancelable

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