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:
16 – 25 October 2021
2 – 11 June 2022
13 – 22 May 2023
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.

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 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
  • All breakfasts, lunches and dinners
  • 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
  • 2 dinners
  • Minibar
  1. Day 1 Orvieto

    Meet at Orvieto station at 14.00 – easy travel, with direct trains from Rome or Florence.
    Relax and settle in. Visit the Cathedral of Orvieto (UNESCO 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.

    Meals: Dinner

  2. Day 2 Civita di Bagnoregio & Orvieto

    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 citadel”.

    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: 3hrs/8km/5m

  3. 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 (UNESCO) via the walled hamlet of Montichiello for a picnic lunch.
    In the afternoon we continue to Pienza (UNESCO) to taste the famous Pecorino sheep’s milk cheese and balsamic vinegar.

    Free time to relax, shop and admire the fine renaissance architecture.

    Meals: Breakfast / Lunch / Dinner

    Walk: 4hrs/13km/8.5m

  4. Day 4 Pienza - Bagno Vignoni – Montalcino

    We walk out of the city gates of Pienza with magnificent extensive views of the Val d’Orcia. By way of trails through scenic farmland made famous in the final scenes of the Gladiator film (1989) and a picnic lunch, we reach the charming hamlet of Bagno Vignoni with its ancient thermal baths adorning the main piazza. Enjoy a relaxing dip in the hot thermal springs. Feeling restored we now take a scenic drive around the base of Monte Amiata (1750m) past three ancient castles that dominate the Orcia river valley. We stop to visit the solitary, Romanesque monastery of Sant’ Antimo built by Charlemagne in 781 before continuing to the finishing point of our day, the walled hill-town of Montalcino which is world-famous for its excellent Brunello wine. After a short stroll through town, we make our way to the battlements of the Rocca castle for a wine tasting.

    Meals: Breakfast / Lunch / Dinner

    Walk: 4hrs/13km/8.5m

  5. Day 5 Cortona

    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.
    After a picnic lunch we continue to Cortona and walk through the ancient city gates to explore its medieval streets and monuments including the renowned MAEC Etruscan museum located in a medieval palace. Now enjoy your free time to 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 & Chianti Classico wine country adventure
    This wonderful day takes us through a gorgeous winegrowing area and some of the most quintessential Tuscan countryside. Our walk has magnificent views stretching from Monte Amiata to Siena and beyond; you can even make out the profiles of Siena’s tallest monuments, the Torre della Mangia and the Duomo. From the characteristic medieval Tuscan village of San Gusme, we walk to the thousand-year-old Castle of Brolio, one of the most impressive castles in Tuscany and the home of the Ricasoli family since 1067! Bettino Ricasoli (d.1880) was responsible for the blend of grapes that gave us Chianti Classico wine and was the 2nd Prime Minister of young and recently-united Italy.
    After a well-earned picnic lunch, 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.
    Meals: Breakfast / Lunch
    Walk: 2hrs/6.5km/4m
  7. Day 7 Gubbio & Monte Ingino

    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 amphitheater 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.

    Meals: Breakfast / Lunch / Dinner

    Walk: 4hrs/13km/8.5m

  8. Day 8 Assisi & Monte Subasio

    Today let’s drive to the picturesque hamlet of Collepino and stop to visit before heading to the start of our trail. From here we take a nice long uphill trail to the top of Monte Subasio (1250m) for 360 views of Umbria, the Apennines and occasionally the Gran Sasso. We can breathe in the fresh scents of the flower-strewn pastures as we traverse the top. This is just the spot for a relaxing picnic before winding on the downhill to Eremo delle Carcere, the tranquil hermitage and favorite retreat of St. Francis. This is a perfect stop before we visit the charming pink-colored town of Assisi (UNESCO) and make our way to see frescoes by Giotto in the Basilica where Francis is buried.

    Meals: Breakfast / Lunch

    Walk: 3-5hrs/8-14km/5-9m; +300/-450m

  9. Day 9 Spoleto & the Olive Tree Trail

    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 (UNESCO), 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.

    Meals: Breakfast / Lunch / Dinner

    Walk: 4-6.5hrs/13-20km/8.5-12m

  10. Day 10 Departure

    Scheduled drop off after breakfast at Spoleto station – direct trains to Rome – or if you wish to depart early or late allow 20 mins in a taxi. If you wish, we can help you make other independent departure arrangements such as early taxis to the airport.

    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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