10 DAYS • 9 NIGHTS
GROUP SIZE: 8 – 12
activity level: MODERATE
FROM € 4,950
DATES & AVAILABILITY
16 – 25 Sept 2026
PRIVATE GROUP
20 – 29 May 2027
FOR PRIVATE GROUPS OR OTHER INFO
Explore Umbria & South of Tuscany on foot with us. Tuscany, the Renaissance capital of Italy and Umbria its green heart, embody Italy’s most picture-perfect landscape.
Feel the influence of the Middle Ages as you walk through Montepulciano’s medieval gates. Admire a beautiful blend of pink stone and terracotta tiled rooves as we descend into Gubbio. Venture along ancient pilgrimage paths and feel the tranquility of a Franciscan hermitage. Explore medieval villages perched on hilltops that are timeless and unchanged, and in tune with both their past and present. See the tomb of St Francis of Assisi and some of the finest frescoes in Italy.
Our journey through Tuscany & Umbria explores Italy’s most picture-perfect landscapes, a region rich in timeless hilltowns and spiritual heritage.
PICK UP: 14.00 at Orvieto train station
DROP OFF: 09.30 at Spoleto train station
We highly recommend arriving in Orvieto a day or two before the tour begins to settle in and shake off any jet lag.
Meet at Orvieto station at 14.00 – easy travel, with direct trains from Rome or Florence.
Walking tour of Orvieto and its incredible Cathedral (UNESCO heritage); the facade simply takes one’s breath away and inside are wonderful frescoes by Fra Angelico and Luca Signorelli. We will also have an introduction to the history and culture of the region before gathering for a welcome dinner of traditional local fare.
Meals: Dinner
Walk: 1.5hrs, 4.5km/2.5mi
Overnight: Orvieto
We begin with a panoramic walk along city walls before exploring the layers of history beneath our feet with a tour of “Orvieto Underground”. This subterranean city was created by ancient inhabitants over 2,500 years of uninterrupted digging.
In the afternoon, we take an excursion to the stunning Civita di Bagnoregio, a small village perched precariously upon eroding rock and accessible only by a causeway bridge.
We return to Orvieto where you can relax and appreciate the historic center as locals emerge to stroll and enjoy a gelato.
Meals: Breakfast, Lunch & Dinner
Hike: 4hrs, 12km/7mi
Overnight: Orvieto
A delightful walk starts in the walled hamlet of Montichiello and follows the country lanes of the Val d’Orcia (UNESCO) to the Renaissance church of San Biagio where we enjoy a picnic lunch.
We enter town through one of the ancient city gates to explore the charming narrow streets of Montepulciano, its magnificent main square and an underground Vino Nobile wine cellar.
Later we continue to Bagno Vignoni (UNESCO) which is famous for its hot springs. Free time to relax and, perhaps swim before dinner.
Meals: Breakfast, Lunch & Dinner
Hike: 4hrs, 13km/8.5mi
Overnight: San Quirico D’Orcia
We walk out of the charming hamlet of Bagno Vignoni with its ancient thermal baths adorning the main piazza. By way of trails through scenic farmland made famous in the final scenes of the Gladiator film (1989) and a picnic lunch along the way, we reach the city gates of Pienza.
You will have free time to wander and enjoy magnificent extensive views of the Val d’Orcia.
Before dinner enjoy a relaxing dip in the hot thermal springs.
Meals: Breakfast, Lunch, Dinner
Hike: 3hrs, 13km/8mi
Overnight: San Quirico D’Orcia
Cortona dominates a vast plain situated on the buttress of Monte Sant’Egidio. We begin with a visit to ancient Etruscan tombs before enjoying a walk among olive groves to a 12th-century hermitage founded by St. Francis. This slender group of stone buildings in a spectacular setting is a profoundly spiritual place.
After a picnic, we continue into Cortona to explore its medieval streets and monuments.
Enjoy free time to visit the world-class MAEC Etruscan museum or simply sit with a cappuccino in an outdoor café.
Meals: Breakfast, Lunch, Dinner
Hike: 3hrs, 10km/6mi
Overnight: Cortona
Today takes us through some of the most quintessential Tuscan countryside.
We head to Siena, Italy’s loveliest medieval city with one of the most richly decorated cathedrals in the world! We will explore the city’s artistic treasures, getting to grips with works by Duccio, Pisano, and Michelangelo. Stand in the famous Campo Square and imagine the pageantry and thundering hooves of the Palio di Siena horse race.
We return to Cortona in the afternoon, where you can enjoy a quiet stroll in the park before dinner.
Meals: Breakfast
City walking tour: 2hrs, 4km/3m
Overnight: Cortona
Assisi (UNESCO) has, for centuries, attracted pilgrims from far and wide. It is the birth and burial place of Saint Francis of Assisi and where superb medieval art tells the story of this very ordinary man.
We visit the church of Santa Maria degli Angeli before entering town for a visit inside the beautifully restored Basilica of St. Francis with its frescoes by Giotto.
After exploring the medieval streets and enjoying a picnic lunch, we take a gentle walk on the high slopes of Monte Subasio, offering magnificent views in every direction.
Our day ends in the delightful town of Spoleto.
Meals: Breakfast, Lunch, Dinner
Hike: 3hrs/8km/5m
Overnight: Spoleto
We start with a walking tour of Spoleto, peeling back layers of history and learning the stories behind the ancient stones.
After lunch in a local cafe we drive a short distance and walk along an olive tree hillside along the Via Francigena pilgrimage route through hamlets untouched by time. If you prefer you can stay and have extra free time to explore more of Spoleto’s many other monuments and treasures.
This evening you are free to absorb the atmosphere and dine at your own leisure.
Meals: Breakfast, Lunch
Hike: 5hrs, 12km/8mi
Overnight: Spoleto
Gubbio is an exquisite town built of warm pink stone. We explore its boutiques and the magnificent Piazza Grande, dominated by the medieval Palazzo dei Consoli. We then ascend by cable car, taking in views of the Roman amphitheatre, to the church of St. Ubaldo perched high on the hillside.
After lunch a walk in the local regional park rewards us with stunning views.
We return to Spoleto for our final celebratory dinner to share our favorite memories of the journey.
Meals: Breakfast, Lunch, Dinner
Hike: 5hrs, 13km/8m
Overnight: Spoleto
10 DAYS • 9 NIGHTS
GROUP SIZE: 8 – 12
activity level: MODERATE
FROM € 4,950
DATES & AVAILABILITY
16 – 25 Sept 2026
PRIVATE GROUP
20 – 29 May 2027
FOR PRIVATE GROUPS OR OTHER INFO
This tour offers a perfect harmony between the “Green Heart” of Umbria and the iconic Renaissance landscapes of Tuscany. You will experience a unique variety of terrain, from walking through the UNESCO-listed Val d’Orcia to exploring the dramatic, bridge-accessible “dying city” of Civita di Bagnoregio. Beyond the trails, the journey is enriched by exclusive cultural touches, such as visiting an underground wine cellar in Montepulciano and relaxing in the ancient thermal waters of Bagno Vignoni.
We meet at 14.00 on Day 1 at the Orvieto train station. This location is easily accessible, with direct train connections from major cities like Rome and Florence.
For international travellers arriving from North America or Australia, we recommend flying into Rome Fiumicino Airport (FCO).
We highly recommend arriving in Italy 1 or 2 days early to overcome jet lag. Staying in Rome is the perfect way to begin your Italian adventure before taking the short train ride to Orvieto on Day 1.
We rate this tour as Moderate, featuring leisurely walks and hikes across undulating hills. You should be prepared to walk between 2km and 12km (1.2 to 7.5 miles) per day, with manageable elevation gains typically ranging from +200m to +310m. The terrain includes a variety of surfaces such as gravel and dirt tracks, ancient Roman basalt tracks, and narrow medieval town streets.
Read more on our Difficulty Level Guide.
The cuisine is a celebration of traditional local fare. You will enjoy welcome dinners of regional specialities and relaxed picnic lunches in stunning locations like the church of San Biagio.
We have selected a collection of unique, locally owned accommodation that balances authentic culture with high-end comfort. You will stay in the heart of beautiful hilltowns, including the ancient city of Orvieto, the medieval jewel of Cortona, and the delightful town of Spoleto. You will also stay in the charming hamlet of Bagno Vignoni, where you can relax in therapeutic natural thermal waters right in the main piazza after a day on the trail.
Our tours are scheduled to take advantage of the most temperate and beautiful seasons, typically Spring and Autumn. These windows offer the best hiking weather, allowing you to enjoy the lush green heart of Umbria and the golden Tuscan hills while avoiding the intense heat and heavy crowds of the peak summer months.
Packing correctly ensures your comfort across varied terrain. Sturdy, well-broken-in walking boots are essential for ancient stone tracks and the varied surfaces encountered each day. We recommend a layering system, including a warm fleece and a high-quality waterproof jacket for changeable weather, along with smart-casual attire for our evening dinners and the local passeggiata. Always pack a sun hat, high-factor sunscreen, and a refillable water bottle to stay protected and hydrated on the trail.
How do I book this tour with Caspin Journeys?
To book, click on the BOOK NOW button next to your preferred departure date on our website or contact us via inquiries@caspin.com
A deposit reserves your spot, and the balance is due ahead of the tour.
Is travel insurance required?
Yes. All participants must have comprehensive travel insurance that covers medical emergencies, trip cancellation, evacuation, and loss/damage of personal items.
Can I join as a solo traveller?
Yes — solo travellers are welcome. In the moment of booking, choose the single room option.
What about tips?
This question comes up a lot. Tips and gratuities for most services during the trip such as restaurant staff, porters etc. are included and handled by Caspin Journeys.
As for your tour leaders we at Caspin leave this gesture to your discretion.
If you have already booked to travel with us,
the link below will redirect you to your WeTravel account — our secure booking platform — where you can manage your booking, check your payment status, and much more.
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