Tuscany & Umbria


Explore this enchanting part of Italy 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 on the Via Francigena and feel the tranquility of a Franciscan hermitage. Admire 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.

Stroll out into a textured painting: a cypress-lined avenue leading into rolling hills with sunflowers, poppies, olives and vines as far as the eye can see. Ascend to Mount Subasio for 360-degree views of the Umbrian landscape and the Apennine mountains. Walk along grassy meadows where horses roam.

In Tuscany and Umbria, you can be sitting with a cappuccino and looking at once at a medieval church, a stone bell tower and a renaissance palace. Turn a corner and you will be tempted by an appetizing array of fresh bread, vegetables and fruit, cheeses and salamis, truffles and mushrooms. Climb the walls onto Montalcino’s castle battlements and look out onto a patchwork quilted landscape.

Almost every town is a destination, so how do you choose where to go and what to see? Don’t worry, we have selected the very best historic sites and monuments, fine dining, and gastronomic delights for you already. Don’t miss out on this small-group walking tour in Tuscany & Umbria.

Tour Dates:
9 – 18 September 2023

You can CONTACT US! or go ahead and BOOK NOW!

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  • Vacation Style Holiday Type
    Walking & Hiking
  • Activity Level Moderate
  • Group Size Small Group
All about the Tuscany & Umbria.

Treasures of Tuscany & Undulating in Umbria

DURATION: 10 days

PICK UP: Orvieto station (direct trains from Rome or Florence)

DROP OFF: Spoleto station (direct trains to Rome)

Discover Tuscany & Umbria with Caspin Journeys

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. 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.

Enjoy views of Mt Subasio, the Umbrian landscape, and the Apennine Mountains. 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 appetising 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.

These are just some of the highlights!

This combined walking and hiking tour in Tuscany and Umbria is unforgettable and not to be missed.

If you would like to speak with us to know more about our Tuscany & Umbria Walking Tour and to get help planning your trip, please write us an email. We would be happy to hear from you and help you plan your next adventure!

*** for more Tuscany tours CLICK HERE! > ***

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 2 experienced guides 24/7
  • breakfasts, lunches and dinners as per itinerary
  • Wine, water & coffee with meals
  • All accommodations
  • Walking sticks
  • All gratuities for hotel porters and waiters
  • Minibus transport from start to finish
  • Entrance fees to museums, events and parks as listed on itinerary
  • Local specialist guiding fees
What is not included in this tour?Items that are not included in the cost of tour price.
  • Flights
  • Transfer to the meeting point
  • Travel insurance and other emergencies
  • Visa fees and entry clearing fees
  • Single room accommodations
  • Minibar
  1. Day 1 Orvieto 4.5km

    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. Introduction to the History & Culture of Tuscany and Umbria, “Italy’s Green Heart”. We enjoy a welcome dinner of traditional local fare.

    Meals: Dinner

    Walk: 1.5hrs/4.5km/2.5m

  2. Day 2 Orvieto & Civita di Bagnoregio 12km

    Panoramic city walls walk of Orvieto which sits majestically on top of a volcanic tufa plateau and a tour of Orvieto underground, 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 citadel”. Afternoon excursion to Civita di Bagnoregio, a small village perched precariously upon eroding rock and reached only by a causeway bridge. Now it is time for you to relax and appreciate the historic town-centre as locals emerge to stroll and enjoy gelato in the early evening.

    Meals: Breakfast / Lunch / Dinner

    Walk: 4hrs/12km/7m

  3. Day 3 Monticchiello - Montepulciano 13km

    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 and 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. Now 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

    Walk: 4hrs/13km/8.5m

  4. Day 4 Bagno Vignoni - Pienza 13km

    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. 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

    Walk: 3hrs/13km/8m

  5. Day 5 Cortona 10km

    Situated on the buttress of Monte Sant’Egidio, Cortona dominates a vast plain. Legend says that it was founded by Dardanus. We begin with a visit to the Etruscan tombs and then enjoy a walk among olive groves to a 12th-century hermitage founded by St Francis. This slender group of stone buildings stands in a spectacular setting and is a profoundly spiritual place for all visitors. We picnic before continuing to Cortona where we walk through the ancient city gates to explore its medieval streets and monuments. Visit the world-class MAEC Etruscan museum in your free time and indulge in a gelato or sit with a cappuccino in an outdoor café.

    Meals: Breakfast / Lunch / Dinner

    Walk 3hrs/10km/6m

  6. Day 6 Siena 4km
    This wonderful day 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! Get to grips with artistic treasures and monuments by Duccio, Pisano, Lorenzetti, Donatello, Pinturicchio and Michelangelo. Last but not least, stand in the Campo Square and imagine the pageantry, the thundering of horses’ feet, and the heated emotional cries of the Sienese as the world-famous horse race, Il Palio di Siena takes place. Back in Cortona you can enjoy a quiet stroll in the park before dinner.
    Meals: Breakfast / Dinner
    City walking tour: 2hrs/4km/3m
  7. Day 7 Assisi & Monte Subasio 8km

    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 S.M.degli Angeli before entering town for a visit inside the beautifully restored Basilica of St. Francis with its frescoes by Giotto. After some time exploring the streets of Assisi and its many other medieval buildings, we stop for a picnic lunch. In the afternoon we enjoy a gentle walk on the high slopes of Monte Subasio with magnificent views in every direction. Our day ends in delightful Spoleto.

    Meals: Breakfast, Lunch, Dinner

    Walk 3hrs/8km/5m

  8. Day 8 Spoleto & the Olive tree trail 12km

    We start the day with a lighthearted walking tour of Spoleto. Enjoy going back in time, peeling back layers upon layers of history. Learn about the stories that lie behind the ancient stones of this special town. 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 (optional). 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

    City walking tour and trail: 5hrs/12km/8m

  9. Day 9 Gubbio 13km

    Gubbio is a medieval gem built of warm pink stone, dating back to the Umbrians who preceded the Etruscans. We explore and admire this exquisite medieval town and its boutiques or observe the locals with a cappuccino in the magnificent Piazza Grande, dominated by the medieval Palazzo dei Consoli building. 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 in the local regional park with stunning views beckons us. We return to Spoleto to relax before meeting to go out for our final dinner together when we can share our favourite memories of our Tuscany and Umbria tour. 

    Meals: Breakfast / Lunch / Dinner

    Walk: 5hrs/13km/8m

  10. Day 10 Departure day

    Scheduled drop off after breakfast at 09.30 at Spoleto station – easy travel, direct trains to Rome – or if you wish to depart early or later allow 20 mins in the taxi. If you wish, we can help you to make other independent departure arrangements such as early taxis to the airport (not incl.).

    Meals: Breakfast

Get lost in the beauty of Tuscany

Live the Authentic Italian lifestyle

Accomodation Standard

A nice hotel and a good night’s sleep are an important part of your overall travel experience!

When considering a hotel, we look at more than just the rooms. We look for hotels or bed and breakfasts which are committed to ensuring their guests are well looked after and pay attention to detail, for example offering locally sourced breakfast produce, or a special selection of toiletries, or tea and coffee making facilities in the room. Wherever possible your hotel* will be perfectly positioned for exploring and will have a historical charm or maybe a new and innovative design. We choose the best possible places to stay ensuring that each night you are comfortably settled in a place that is welcoming and full of authentic local charm. We are on a mission to find the ingredients you need to wake up feeling rested and looking forward to each day of your Caspin Journeys tour!

Take a closer look at some of the places we have chosen for you…

  • Orvieto 2 nights
  • Pienza 2 nights
  • Cortona 2 nights
  • Spoleto 3 nights

*Hotel selection may vary

Tuscany & UmbriaSome of the dream hotels you will find on this tour
An old Palace in Cortons
View of the Duomo in Orvieto
A noble family home in Spoleto

Click here to send us an email with your enquiry. If you prefer us to call you back, please provide also your telephone number and the best day and time suite you to receive a call from us.

Yes, it’s possible.

Once you have chosen your tour, click on the Book Now button. It will redirect you to our online booking form. Once you have payed a 25% deposit out of the total tour price, you can consider your booking confirmed.

Feel free to decide the best payment method for your needs! We accept credit/debit cards and bank transfer.

Please don’t hesitate to contact us if you have any other requirement.

When it will be time to pay the balance, we will send you an email with the payment request. We will assist you through all the steps and we will be available to answer to all your questions.

Absolutely, no problem!
Request our bank details:

We will be happy to assist you with your booking!

We recommend you fly in to Rome or Florence (Firenze) Airport.

Pick up for this tour is at Orvieto train station, which has a direct rail connection to Rome or Florence. N.B. You may have to use the airport rail shuttle and then change trains at the main railway station.

Drop off is at Spoleto train station, which has a direct connection to Rome.

If you plan on arriving a few days early it is easy to just hop back on a train to Orvieto from Rome or Florence.

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