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 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.

Day 2: Explore the extraordinary hill town of Pitigliano, also known as "Little Jerusalem", and the 7th-century village of Sovana.

Day 3: Walk in the beautiful Uccellina Nature Reserve, characterized by expansive beaches and steep cliffs. Transfer to the hill town of Montalcino. Indulge in tasting one of Italy's best red wines, the famous Brunello.

Day 4: Amble through vineyards, farmlands, and olive groves to the Abbey of Sant' Antimo and listen to the monks' Gregorian chants.

Day 5: Today's walk brings us through the enchanting town of Castelmuzio and on to Pienza, a UNESCO world heritage site and the home of the monestary where "The English Patient " was filmed. This afternooon we transfer to the hilltop village of Spello. Dinner brings a feast of the culinary specialties of Umbria, a region of distinctive styles and flavors.

Day 6: Visit the medieval village of Gubbio, and the Basilica of Saint Francis in Assisi. End the day with a tasting of Umbria's fine local vintages.

Day 7: Hike through the natural Park of Mounte Subasio through one of the most beautiful landscapes in Umbria. Enjoy a celebratory dinner in a nearby exclusive restaurant.

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

THE BOUNDLESS JOURNEYS' ADVANTAGE

• A passion for travel. Simply put, we love to travel, and that is woven into every one of our journeys.
• Unique, award-winning itineraries. Our flexible, hand-crafted journeys have received accolades from the world’s most revered travel publications.
• Insider connections. There is simply no substitute for traveling with a knowledgeable insider.
• Small groups. We tread softly, and our average group size is just 6-8 guests.
• Flexibility to suit your travel style. We offer both small-group departures and Private Collection trips.
• Customer service that goes the extra mile. There is no request that is too big – or too small.
• Sustainability. We are committed to traveling responsibly.

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.

WHAT TO EXPECT

Physical Activity
Boundless Journeys’ trips are designed for energetic and flexible individuals who like to be active and have a spirit of adventure and a positive attitude. A Taste of Tuscany & Umbria is rated 2, easy to moderate, on a scale of 1-5 (with 5 being the most strenuous). It features walks of varying length and difficulty that average 3-6 hours per day. Our van will usually meet us midday, and our luggage is transported for us, so it is always possible to ride in the van if you want to opt out of a day’s walking. Please refer to the detailed itinerary for descriptions of the activities on each day of the trip. 

Preparing for this Trip
The more well-prepared you are for the activities on this trip, the more you will enjoy yourself! Please engage in moderate aerobic activities (walking, jogging, or cycling) for at least 30-45 minutes several times a week for 4-6 weeks before the trip. If you live in a flat area, try to incorporate some stairs into your workout, or use a treadmill with varying incline capability. Consult your doctor before undertaking any new fitness programs. 

What the Trip is Like
A Taste of Tuscany & Umbria will expose you to some of the finer aspects of these special areas, and allows for an intimate experience as we set out on foot through the beautiful landscape and picturesque hill towns. The accommodations we have chosen are some of the finest in the region, and are in ideal locations offering views of broad valleys and rolling countryside. Our meals are chosen to introduce you to regional specialties and they may be taken as a picnic, in a lively trattoria, or as a multi-course meal in an elegant setting; all will be memorable! Wine and olive oil tastings expose us to the subtle differences between the regional varieties, and provide yet another taste of la dolce vita.

Weather
The weather in late spring and early fall is usually very pleasant, with daytime temperatures that range from low 60’s to upper 70’s, and evening temperatures in the 50’s. While these months are not in Italy’s “rainy season”, there can be cool breezes or showers at any time.

You may obtain more detailed weather information at www.weatherbase.com.

When to go
In spring, the wildflowers are in bloom and mauve wisteria cascades over stone walls in village gardens. The countryside is a sea of green slashed with masses of scarlet poppies and scented with fragrant yellow broom. Temperatures are still too cool for swimming, but ideal for walking. In fall, the weather is usually warmer and the hotel pool beckons. Vineyards drip with purple grapes as the harvest begins.

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

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

After lunch, we meet in the historic center of Siena and 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.
Relais Villa Acquaviva, Montemerano

DAY 2
Etruscan trails of Pitigliano and Sovana

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

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 the continue to the charming 7th-century village of Sovana. We take time to explore the history and architecture of this small wonder.

If time and weather permits, we may decide to take a soak in the hot springs of Saturnia, famous for its therapeutic qualities, before returning to our villa. We enjoy dinner this evening at a very special restaurant in the heart of Montemerano.
Relais Villa Acquaviva, Montemerano

DAY 3 
Uccellina Nature Reserve; transfer to Montalcino

Walk – 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 coast 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.

After lunch 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 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, Re di Macchia. Here we are treated to many Tuscan delicacies, such as Florentine steak, tiramisu, and panna cotta, as well as a sampling of the fine wines from the region.
Hotel Dei Capitani, Montalcino

DAY 4 
Montalcino to the Abbey of Sant’Antimo

Walk – 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, where we might discover the best wild boar in Tuscany, 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

DAY 5 
Montalcino to Pienza; transfer to Spello

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

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.

We are free to have lunch on our own in the town of Castelmuzio, an enchanting and well-preserved medieval village dating back to the time of the Etruscans, before continuing on a mile and a half panoramic walk 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.  Here we have a chance to taste the famous pecorino cheese, and you may even want to vacuum seal some to bring home!

This afternoon 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 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.

This evening we enjoy a grand welcome to Umbria with dinner prepared by chef Marco Gubbiotti at our hotel restaurant. 
La Bastiglia, Spello

DAY 6
Gubbio

Walk – 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 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 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.

After lunch, we explore this ancient town, founded by the Etruscans and conquered by the Romans, with a walk through its piazzas, churches, public palace, and ceramic shop, carrying on the tradition of the great renaissance artist Mastro Giorgio. 

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.

Our day ends in a medieval wine cellar for a tasting of Umbria’s fine local vintages. This evening you are free to continue your exploration of Spello as dinner is on your own.
La Bastiglia, Spello

DAY 7 
Mounte Subasio

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

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 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 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.
La Bastiglia, Spello

DAY 8 
Assisi

Walk – easy, 1-2 hours on quiet 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, a short drive brings us to Foligno where you may 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.
 

$4,095 per person; 2011 Land Cost: $4,295 per person

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