Tuscany & Umbria

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Explore this enchanting part of Italy with us at a walking pace. Tuscany and Umbria embody Italy’s most iconic and classic landscapes – tall and towering cypress trees lining chalky farm roads, rolling hills that stretch as far as the eye can see, fields of vines and poppies and medieval villages perched on hill tops, timeless and unchanged and in tune with both their past and present.

It is a top-ten destination; 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 including staying in luxurious accommodations in places like Orvieto, Siena and Assisi!

Don’t miss out on this small group walking tour in Tuscany, Renaissance capital of Italy and Umbria, Italy’s Green Heart.

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  • Vacation Style Holiday Type
    Walking & Hiking
  • Activity Level Leisurely
  • Group Size Small Group
All about the Tuscany & Umbria.
Discover Tuscany & Umbria with Caspin Journeys

PICK UP: Orvieto station (direct trains from Rome or Florence)
DROP OFF: Spoleto station (direct trains to Rome)

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 or call 800.908.1980. We would be happy to hear from you and help you planning 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
Whats 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
  • 1 lunch & 1 dinner
  • 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.

  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. (total walking time 3hrs; distance 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. (walk 4hrs/13km/8.5m)

  4. Day 4 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 hear 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)

  5. Day 5 Cortona

    Visit the Etruscan tombs and enjoy a walk among olive groves past a XII century Franciscan hermitage followed by a picnic before continuing to Cortona via the ancient city gates to explore its medieval streets and monuments.
    Visit the renown MAEC, the beautiful 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)

  6. Day 6 Chianti valley - 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)

  7. 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)

  8. Day 8 Monte Subasio - 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 (UNESCO) to see frescoes by Giotto in the Basilica where Francis is buried. (walk 3-5hrs/8-14km/5-9m; +300/-450m)

  9. Day 9 Olive Tree Trail - 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 (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. (walk 4-6.5hrs/13-20km/8.5-12m).

  10. Day 10 Departure

    Scheduled drop off at 8.00 or 10.00 at Spoleto station – easy travel, direct trains to Rome – or if you wish to depart later allow 20 mins in the taxi. If you wish, we can help you to extend your stay or make other independent departure arrangements such as early taxis to the airport.

Get lost in the beauty of Tuscany

Live the Authentic Italian lifestyle

Accomodation Standard

Accommodations are an important point of your overall holiday experience. One of our first thought is to find and choose the best hotel and b&b solutions, ensuring that each night of your itinerary finds you comfortably settled in a space that is welcoming and full of authentic local charm.

When considering a hotel, we look at more than just the rooms and wherever possible, we arrange for stays close to the places you most dream of seeing like historically iconic, coveted high-design or supremely located at the edge of a wilderness.

Take a closer look at some of the properties we have chosen for your next Caspin Journeys holiday!

Tuscany & UmbriaSome of the dream hotels you will find on this tour
Hotel San Michele
Hotel Duomo
Palazzo Dragoni

    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.


    Yes, absolutely!
    Here are our bank details:

    EURO payments:

    • Account: Caspin Journeys Ltd, 65 Randall Rd, Kenilworth, CV8 1JX, United Kingdom
    • IBAN: BE39 9670 5104 6719
    • Bank Address: TransferWise Europe SA, Avenue Marnix 13-17, Brussels, 1000 Belgium

    GBP payments:

    • Account: Caspin Journeys Ltd, 65 Randall Rd, Kenilworth, CV8 1JX, United Kingdom
    • Account no. 91437267, Sort code 40-26-04
    • IBAN: GB54HBUK40260491437267
    • BIC / SWIFT: HBUKGB4104W
    • Bank Address: HSBC Bank Plc, 46 the Square Kenilworth, CV8 1EA

    Don’t hesitate to call us 1-800 -9081980 for any questions. We would be happy to assist you with your booking!


    We recommend you fly in to Rome Airport.

    Pick up for this tour is from Orvieto train station, which has a direct connection to Rome.

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

    If you plan on arriving a few days early and will not be flying in on pick up day, contact us and we can work together to arrange a more convenient pick up location for you.

Package Confirmed Dates Trip Status Trip Status Price (PP) Shared Occupancy Price (PP) Single Occupancy 
16th October 2021 - 25th October 2021