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  • Italy: Tuscany & Umbria Walking
Overview

Get a Taste for Italy’s Idyllic Countryside with Boundless Journeys

The landscape of neighboring Tuscany and Umbria is soul-stirring, with its sweeping vistas, fascinating history, and unique culture and architecture. This is a place where the union of art and nature has been celebrated for thousands of years, and Boundless Journeys’ Tuscany & Umbria Walking Tour is a perennial favorite that will take you through Italy’s renowned countryside, down ancient footpaths, across fertile valleys, and through picturesque towns.

Enjoy daily walks through stunning landscapes with vineyards, olive groves, cypress trees, and storied hill towns. Visit medieval places like Montalcino, Pienza, Assisi, and Spello, as well as the Maremma region of Tuscany, with its Etruscan sites and Italian cowboys.

Tuscany and Umbria are also regions of incredible flavors, so your adventure will be as much a culinary and Italian wine tour (complete with a Tuscan cooking class) as it is a walking tour. At day’s end, you’ll relax in the region’s most charming hotels and savor delicious Tuscan cuisine complemented by unforgettable local wines. Raise a glass to la dolce vita on this Tuscany & Umbria Walking Tour with Boundless Journeys!

What Our Guests Have To Say About This Tour

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Itinerary &
Accommodations

Itinerary & Accommodations

Day 1

Meet in Florence; Transfer to Siena & Montemerano

  • Activity Overview: Walking on pedestrian streets
  • Activity Level: Easy
  • Activity Length: 2-4 hours

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

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.

Day 2

Etruscan Trails of Pitigliano & Sovana; Cooking Class

  • Activity Overview: Walking along country roads and trails
  • Activity Level: Easy to moderate
  • Activity Length: 3-5 hours (approximately 5 miles)

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.

Upon 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

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.

Day 3

Rupestrian settlements of Vitozza and San Rocco, and the town of Sorano; transfer to San Quirico d'Orcia

  • Activity Overview: Walking along trails
  • Activity Level: Easy to moderate
  • Activity Length: 3.5 hours (approximately 4.5 miles); 1 hour optional afternoon walk (approximately 1 mile)

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 Francigina, 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

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.

Day 4

Walk to Bagno Vignoni, Il Cerreto countryside lunch; Ridge walk along the Orcia Valley, Pienza

  • Activity Overview: Walking along country roads and trails
  • Activity Level: Easy to moderate
  • Activity Length: 3.5 hours (approximately 5 miles)

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 caffè 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

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.

Day 5

Montalcino to the Abbey of Sant'Antimo

  • Activity Overview: Walking along country roads and trails
  • Activity Level: Easy to moderate
  • Activity Length: 3-4 hours (approximately 5 miles)

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. 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.

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. 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

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.

Day 6

Gubbio

  • Activity Overview: Walking along country roads and trails
  • Activity Level: Easy to moderate
  • Activity Length: 3-5 hours (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 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

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.

Day 7

Monte Subasio

  • Activity Overview: Walking along country roads and trails
  • Activity Level: Easy to moderate
  • Activity Length: 4-6 hours (approximately 8 miles)

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

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.

Day 8

Assisi

  • Activity Overview: Walking on city streets
  • Activity Level: Easy
  • Activity Length: 1-2 hours

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.

Please note that this is a typical itinerary, and actual activities may vary due to 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 or the order visited should the need arise.

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Dates &
Prices

Dates And Prices

2016
Trip Length

8 Days

Trip Dates

Oct 2-9, 2016

2016 Land Cost

$4,495 Per Person


Single Supplement

First two reserved:$140

Additional:$640

See single supplement policy below.

2017
Trip Length

8 Days

Trip Dates

May 21-28, 2017

Sep 10-17, 2017

Oct 1-8, 2017

2017 Land Cost

$4,695 Per Person


Single Supplement

First two reserved:$125

Additional:$625

See single supplement policy below.

What's Included

  • Expert leadership
  • All accommodations
  • All meals except one lunch (Day 8) and two dinners (Days 4 & 6)
  • Local wine and beer with included dinners
  • All activities as noted in the itinerary
Single Supplement Policy

Accommodations (hotels, tents, cruise cabins) are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability. If you reserve at least 120 days prior to departure, you may be eligible for a reduced or free single supplement.* This is generally limited to the first one or two solo travelers to reserve, and the reduction is outlined in the pricing for each trip. Please note, free or reduced single supplements are not combinable with other offers or promotions.

If you are traveling alone and wish to share accommodations, we will try to match you with a roommate of the same gender. If you reserve at least 120 days ahead and a roommate is not available, you will only be charged a “forced” single supplement in the amount of 50% of the standard single supplement* (unless otherwise noted in the detailed itinerary). Single accommodations are limited so you are encouraged to reserve early!

* This does not apply to cruises in the Galapagos Islands. Please see these trip pages for more details.

What To
Expect

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. Italy: Tuscany & Umbria Walking 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. There are no extended climbs, most walks are over gentle, rolling hills; some terrain can be uneven and rocky.

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.

Meeting Point

Florence, Italy at 10:00 a.m.

Departure Point

Assisi, Italy at 1:30 p.m.

Traveling To and From

Most Convenient Airport:
Amerigo Vespucci Airport in Florence (airport code FLR)

Meeting Time and Place:
10:00 a.m. in front of the Hotel Palazzo Lucchesi, Florence

Departure Time and Place:
Your guides will provide transportation to the Assisi train station by 1:30 p.m., and from there it is easy to catch trains to other cities in Italy.

Preparing for this Trip

As a general guideline, we suggest that you engage in easy to moderate aerobic activities (such as walking, hiking, 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 program). Please contact us if you have any doubts regarding your physical match with this tour.

What the Trip is Like

Boundless Journeys' Italy: Tuscany & Umbria Walking will expose you to some of the finer aspects of these special regions, and allows for an intimate experience as we set out on foot through beautiful landscapes 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!

Weather

The weather in early fall is usually very pleasant, with daytime temperatures that range from the low 60s to the upper 80s, to the 50s and 60s at night. While September and October 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.

Tuscany & Umbria

September

High: 75
Low: 58

October

High: 65
Low: 51

When to Go

In fall, the weather is usually temperate and the hotel pool beckons. Vineyards drip with purple grapes as the harvest begins.

Guides

Featured Guides

About Our Guides

With a Boundless Journeys guide, your experience is that of friend and local adventurer. We believe strongly in working with local guides, experts in the areas to which we travel, and they hold the keys to unlocking the hidden delights of your chosen destination. Although you will never know they are at work—the mark of a truly great leader—our guides make magical things happen and add a dimension to your trip that you could not experience on your own. Over the years we have forged bonds with some of the best guides in the world, and we typically work with a small team of guides in each region. You will be informed of the guide for your trip one month prior to your departure.

$4,495 / person* *airfare not included
8 Days
Reserve This Tour
  • Departure Dates: Oct 2-9, 2016
    May 21-28, 2017
    Sep 10-17, 2017
    Oct 1-8, 2017
Activity Level 2 Easy to Moderate

Easy to moderate walking and hiking, 3-6 hours per day.

  • Group Size: 4-16 Guests

Make it Your Own!

This trip can be your own adventure by taking over one of our scheduled dates, or we can request a fresh one.

Prefer a Custom Tour?

Questions?

Our dedicated team of travel experts are here to help.

1-800-941-8010

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