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"Treasured Tuscany & Undulating Umbria"

 Our small group walking tour in Tuscany and Umbria take us to see treasures in two rural regions that have remained enchanting and unchanged throughout the ages. Timeless Tuscany and Unspoilt Umbria are in tune with both their past and present. Feel the influence of the Middle Ages, the Church and the Renaissance as you walk through the gates of medieval Montepulciano. Admire a beautiful blend of pink stone and terracotta tiled roofs as you descend into Gubbio.

Venture along ancient pilgrimage paths on the Via Francigena and feel the tranquility of a Franciscan hermitage. See the tomb of St Francis of Assisi among some of the finest frescoes in Italy – these are just some of the highlights. Stroll out into a textured painting: a cypress lined avenue leading onto rolling hills with sun-flowers, olives and vines as far as you can see.

Ascend to Mt Subasio for 360 degree views of the Umbrian landscape and the Apennine Mountains and walk along grassy meadows where horses roam. Sit with a cappuccino in the square of Siena; you will be looking at once at a medieval church, a stone bell-tower and a renaissance palace. Turn a corner and you will and be tempted by an appetizing array of fresh bread, vegetables & fruit, cheeses & salamis, truffles and mushrooms. Climb the walls onto the castle battlements of Montalcino and look out onto a patchwork-quilt. This combined walking and hiking tour in Tuscany and Umbria is an unforgettable and not to be missed. 





Duration: 10 Days/ 9 Nights
Group size: max 10
Activity Level: Moderate
Meet / Depart:  Orvieto station / Spoleto station
Traveling Solo: Contact us for details

from € 3,595

per person shared occupancy 

Included in the Tour:

All accommodation
All meals – except 1 lunch & 1 dinner
Wine, water & coffee with meals
All transport within the tour
Everything except postcards, stamps and phone calls
No hidden extras!!


Small Group walking tour tuscany & umbria

| DAY 1 | Meet in Orvieto Station

(Easy travel – Direct trains from Rome or Florence)

Meet at Orvieto station at 14.00. Relax and settle in. Visit the Cathedral of Orvieto (World Heritage) whose facade simply takes one’s breath away; inside are wonderful frescoes by Fra Angelico and Luca Signorelli.  Introductory talk: History & Culture in Tuscany and Umbria, “Italy’s Green Heart” accompanied by light refreshments. We enjoy a welcome dinner of organic local fare.


Small Group walking tour tuscany & umbria -siena-duomo-guided tours| DAY 2 | Civita di Bagnoregio & Orvieto’s underground world

Morning excursion to Civita di Bagnoregio, a small village perched precariously upon eroding rock and reached only by a causeway bridge. We return to Orvieto which sits majestically on top of a volcanic tufa plateau to make our way through the narrow streets and take a tour of Orvieto’s ‘underground city’, created by its ancient inhabitants over about 2500 years of uninterrupted digging. An hour-long tour on a discovery of a millenary, surprising and unexpected “Underground City”. Now it is time for you to relax and enjoy the historic town-centre as locals emerge to stroll and enjoy gelato in the early evening. (total walking time 3hrs; distance 8km/5m)


| DAY 3 |  Montepulciano – Monticchiello – Pienza

We walk through the narrow streets of Montepulciano to its magnificent main square and then down through ancient wine cellars to the Renaissance church of San Biagio. From here we depart through the cypress lined avenue and then along country lanes into the Val d’Orcia via the walled hamlet of Montichiello for a picnic lunch. In the afternoon we continue to Pienza to taste the famous Pecorino sheep’s milk cheese and balsamic vinegar. Free time to relax, shop and admire the fine renaissance architecture. (walk 4hrs/13km/8.5m) UNESCO heritage site


Sant-Antimo-Montalcino-Private-Best-Hiking-Tours-Caspin-Journeys-Image | DAY 4 | The Abbey of Sant’Antimo – Montalcino

We start our walk at the battlements of the Castello di Ripa D’Orcia with magnificent views of the River Orcia below. By way of trails through farmland and vineyards we reach the Romanesque monastery of Sant’ Antimo, founded by Charlemagne in 781. If we are lucky we can here the monks chanting one of the services before continuing to the hill-town of Montalcino for free time and a Brunello wine tasting at the medieval Fortress.(walk 4hrs/13km/8.5m)



| DAY 5 |  Exploring Cortona

Visit the Etruscan tombs and enjoy a walk among olive groves past a 12th Century Franciscan hermitage followed by a picnic before continuiing to Cortona via the ancient city gates to explore its medieval streets and monuments. Visit the Etruscan museum and then free time to indulge in a gelato or sit with a cappuccino in an outdoor cafe. (walk 2.5hrs/8km/5m)




| DAY 6 | Chianti wine country & Siena

Excursion to the Chianti wine country to walk from Brolio castle to San Gusme. After a picnic lunch we head to Siena. We visit one of the most richly decorated cathedrals in the world with masterpieces by Duccio, Pisano, Lorenzetti, Donatello, Pinturicchio and Michelangelo. In the Campo Square we learn about the world famous Palio horse race. (walk 2hrs/6.5km/4m)




  | DAY 7 | Gubbio 

Gubbio is a medieval gem built of warm pink stone, dating back to the Umbrians who preceded the Etruscans. We explore the medieval town, admire the local ceramics and see the Egubine tablets in the Palazzo dei Consoli. Observe the locals with a cappuccino in the magnificent Piazza Grande. We then ascend by cable car with views of the Roman amphitheatre to the church of St. Ubaldo, perched on the edge of the hillside and inside the relic of the saint himself. After a picnic lunch a walk with stunning views beckons us. (walk 4hrs/13km/8.5m)


Basilica-St-Francis-Assisi-Umbria-Walking-Trips-Caspin-Journeys-Image | DAY 8 | The Olive Tree Trail to Spoleto

A walk among olive groves and along the Via Francigena Pilgrimage route through hamlets untouched by time and ending on the outskirts of Spoleto at the Basilica of San Salvatore, one of Italy’s oldest churches built temple-style using Roman materials. This is a beautiful and rewarding full day’s walk and there are options during the day for those who may prefer to spend the afternoon in Spoleto visiting its Roman quarter, enjoying the medieval atmosphere and viewing the castle and aqueduct. (walk 4-6.5hrs/13-20km/8.5-12m) UNESCO heritage site.



  | DAY 9 | The Mountain and Town of St Francis of Assisi 

Today we drive to the picturesque hamlet of Collepino and stop to visit before heading to the start of our trail. We ascend +200m along the flower-strewn pastures to the top of Monte Subasio (1250m) for 360` views of Umbria, the Appenines and occasionally the Gran Sasso. Just the spot for a picnic, after which we wind downhill to Eremo delle Carcere, the tranquil hermitage and favorite retreat of St. Francis, a perfect stop before we visit Assisi to see frescoes by Giotto in the Basilica where Francis is buried. (walk 3-5hrs/8-14km/5-9m; +300/-450m) UNESCO heritage site


|  DAY 10 | Departure from Spoleto station

(Easy travel – Direct trains to Rome)

Scheduled drop off at 8.00 or 10.00 at Spoleto station or if you wish to depart later allow 20 mins in the taxi. 










Orvieto; 2 nights
Cortona; 5 nights
Spoleto;  2 nights

Tour Prep

Some useful links for you to use while getting ready for your tour.

The secret of our small group walking tours lies in choosing exciting itineraries and turning them into relaxing vacations for others to enjoy. A journey with us is like a chapter in a good book you cannot put down, a discovery trail of treasures, an active vacation outdoors where you meet like-minded people and create wonderful memories to take home.


We offer you the luxury to relax, be carefree and totally immerse yourself in the local atmosphere, making the most of your precious time.
We take care of all the logistical arrangements and tiny details you would hope to think of if only you had the time.


Our priority is to give you a tour of the highest standard and excellent value for money;  prices are fully inclusive with no hidden extras. We believe you will only need to buy postcards and the occasional cappuccino.


We are unique through our personal devotion to your tour. We don’t rely on others to provide the quality and service we expect, we make sure it happens ourselves.
We spend a lot of time finding attractive walks and seeking the best places to visit. We take small groups and guide all our own tours employing local experts where detailed knowledge is beneficial.

Other small group tour ideas:

Puglia, Basilicata & Matera

The sun-blessed heel of the Italian peninsula boasts monuments like the Trulli houses and Matera’s cave dwellings, where a traveler exploring on foot can enjoy breathtaking sea views, rugged coastal scenery and vast expanses of ancient olive groves seemingly untouched by time.

Amalfi, the Coast of Emotions

Sensational coastal scenery of limestone cliffs, serpentine roads and terraced lemon groves with famous towns like Amalfi, Positano and Ravello. Villages and remote monasteries here have long been connected by a series of ancient footpaths perfect for walking and hiking.