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.
Italy Walking Tour Overview
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.
Italy Itinerary at a Glance
Day 1: Meet in Florence and transfer to Siena. Enjoy a walking tour through the vibrant pedestrian streets of this fascinating city. Transfer to the lovely town of Montemerano for a wine tasting and dinner.
Day 2: Explore the extraordinary hill town of Pitigliano, and the 7th-century village of Sovana. Learn to make Tuscan specialties in a cooking class and dine on the fruits of our labor.
Day 3: Discover the Rupestrian settlements of Vitozza and San Rocco, and the ancient town of Sorano. Transfer to the charming village of San Quirico d’Orcia.
Day 4: Walk along the pilgrimage route linking Canterbury to Rome, to the small town of Bagno Vignoni, known for its curative thermal waters. Enjoy lunch at a 16th-century farmstead, where we are treated to a tasting of pecorino cheese, as well as homemade jams and olive oil. Discover the Renaissance town of Pienza, a UNESCO World Heritage Site since 1996.
Day 5: Amble through vineyards, farmlands, and olive groves to the Abbey of Sant’Antimo and listen to the monks’ Gregorian chants. This afternoon transfer to Umbria, making our home in the hilltop village of Spello.
Day 6: Visit the classically picturesque village of Gubbio. Learn about the Basilica of Saint Francis in Assisi with a guided tour.
Day 7: Hike through the natural Park of Monte Subasio, one of the most beautiful landscapes in Umbria.
Day 8: Visit Assisi, the enclosed city full of churches, Roman temples, and castles. Transfer to the local train station and say arrivederci.
The Italian Experience
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.
Our tours often fill months in advance, and our maximum group size is smaller than most tour operators. It's very quick and easy to reserve a trip. Give us a call at 800-941-8010 or complete the online Reserve a Trip form. We will confirm your reservation with a $500 per person deposit, payable by check or credit card.
Trip Rating (1 Easiest - 5 Most Strenuous)
Traveling to and From
Most Convenient Airports:
Amerigo Vespucci Airport in Florence (airport code FLR)
Meeting Time and Place:
10:00 a.m. in front of the Classic Hotel, 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.
WHAT TO EXPECT
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. 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. 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 would like 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
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!
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 and 60'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
|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: Palazzo del Capitano Wellness & Relais
San Quirico d’Orcia, Italy
|A renovated antique residence from the 14th century, this hotel is situated in the splendid medieval village of San Quirico, in the heart of Val d’Orcia. Filled with charm and furnishings that recall Tuscan traditions, the Relais also offers a beautiful garden where you can unwind under the shadow of ancient olive trees and colorful fountains.|
Nights 5, 6, & 7: Hotel la Bastiglia
|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.|
A Boundless Moment in Tuscany...
From a distance, the Abbey of Sant’Antimo came into view, nestled in a hillside flanked by Cyprus trees. Reaching it, we part the heavy wooden doors and are greeted by the soft, ethereal tones of a Gregorian chant, echoing from deep within the naves. Our guide says the monks here have been singing this way for more than 800 years, and today, it seems, the past is very much at hand.
ITALY DETAILED ITINERARY
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 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.
Relais Villa Acquaviva, Montemerano
Etruscan trails of Pitigliano and Sovana; cooking class
Walk – easy to moderate, 3-5 hours along country roads and trails (approximately 5 miles).
Today we explore the extraordinary hill towns of Sovana and Pitigliano, each rich in Etruscan remains. The Etruscans were mysterious people who 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.
Relais Villa Acquaviva, Montemerano
Rupestrian settlements of Vitozza and San Rocco, and the town of Sorano; transfer to San Quirico d’Orcia
Walk – easy to moderate, 3.5 hours along trails (approximately 4.5 miles); optional afternoon walk – moderate, 1 hour along trails (approximately 1 mile).
This morning’s hike takes us from the small village of San Quirico di Sorano 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 Middles 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, with decorated portals 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.
Palazzo del Capitano Wellness & Relais, San Quirico d’Orcia
Walk to Bagno Vignoni, Il Cerreto countryside lunch; Ridge walk along the Orcia Valley, Pienza
Walk – easy to moderate, 2 hours along country roads and trails in the morning, and 1.5 hours along countryside roads in the afternoon (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.
Palazzo del Capitano Wellness & Relais, San Quirico d’Orcia
Montalcino to the Abbey of Sant’Antimo
Walk – easy to moderate, 3-4 hours along country roads and trails (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.
La Bastiglia, Spello
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 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.
La Bastiglia, Spello
Walk – easy to moderate (with a 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 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.
La Bastiglia, Spello
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 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 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.
- Sep 04–11, 2016
- Oct 02–09, 2016
2016 Land Cost
$4,495 per person
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.
- Expert leadership
- All accommodations
- Wine and cheese tastings
- Tuscan cooking class
- All meals except one lunch and two dinners
- Table wine with included meals
Please complete the following information to request a reservation. A trip deposit of $500 per person is required to confirm your reservation (payable by check or major credit card). Once we receive your request we will contact you within one business day to confirm availability and answer any questions you may have.
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.
Alex Gullo: Since 1998, Alex has been a walking guide throughout Italy, from the Dolomites to Sicily, enjoying sharing Italy from all points of view - the natural beauty, the food, the wine, and the historical sites, with a particular look at the Italians of today. In return, he most enjoys the guests sharing a week of their life with him. Educated in the U.S. as well as Italy, he is a certified guide of historic monuments in certain Italian regions. He combines his charming personality with a vast knowledge to make our Italian adventures more than memorable.
Keegan Alagna: With an American mother and an Italian father, Keegan grew up in a bilingual home enriched with insights into two cultures and two countries. He grew up on a working farm in the Assisi countryside, and developed a passion for the natural world and the outdoors at a young age. During Keegan’s post-graduate work in geology at the Università di Perugia, his research often took him abroad where he consulted on volcanic phenomena. Keegan continues to pursue his interest in geology and the outdoors through participation in hiking programs with the Club Alpino Italiano, and in creating geology programs for the Italian schools. Keegan currently lives in Orvieto, and enjoys leading walking tours with a focus on Italy’s history, its natural wonders, and the Italian people.
Elizabeth Namack: Elizabeth first came to Italy 20 years ago as an American college student to study Art History and Italian Literature. She quickly fell in love with all things Italian! Her interest in regional wine and cuisine – coupled with her academic background in art history and painting restoration – make her a delightful traveling companion. Elizabeth lives with her husband and son a block away from the Arno River in Florence. In addition to a strong love of the outdoors, she is an official guide for the city of Florence. When not leading guests along the picturesque backroads of Tuscany and Umbria, she leads engaging art tours in this marvelous city.
What other Boundless Journeys guests have said about our Tuscany & Umbria guides:
Alex, our guide, was not only very professional but became one of us and made our journey totally fantastic; the tour was well structured and organized; the walks were different every day and each one was more beautiful than the other!!! The landscapes and views of Tuscany and Umbria were all breathtaking; the hotels, food, wines etc were all extremely well chosen and of the highest quality. In summary it was one of the most memorable and precious adventures and journeys we have ever had and we will treasure it for the rest of our lives!!! Thank you for your help and for giving us this incredible opportunity . . . really, we can’t thank you enough!!!” – M.W. & J.W., Boca Raton, Florida
"The entire trip was exceptional. Our guide was terrific. You could tell how much he enjoyed his work and his country, and how much he enjoyed telling people about it! Of course the weather certainly helped make the trip one-of-a-kind – 75 degrees and sunny every day. Did you guys arrange that too?!" – G.H. & C.B., Boston, MA
"Our guide set the tone; her passion, expertise, sense of humor and openness made for a wonderful experience! Grazie mille!" – L.Z., Alberta, Canada
"Alex went out of his way to create opportunities for us to experience local culture – meeting a friend who invited us into his home for a glass of wine, getting a spontaneous tour of a private palazzo in Gubbio, meeting a medievalist scholar in his small apartment in Assisi – these enriched our days, already rife with interesting commentary." – R.W. & L.W., Huntingdon Valley, PA
Picture Yourself Here:
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
Maremma region of Tuscany, with its Etruscan sites and Italian cowboys
Tuscan cooking class, wine and cheese tastings, and fine accommodations
- Sep 04–11, 2016
- Oct 02–09, 2016
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What others have said...
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'.
- D.C., Centerport, NY
Latest Blog Posts About Italy
"Charlie was a fantastic guide. I do not know where you find these guys! Every guide we have had with Boundless Journeys has been amazing! Thank you for a great experience (again!)."
- Tim & Holly Lofton, Chile: The Lake District & Patagonia