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Treasured Tuscany & Undulating Umbria

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Trip at a Glance

  • Company

    Caspin Journeys Ltd

  • Locations

    Tuscany, Italy

  • Activities

    Adventure, Hiking Trekking

  • Price
    €3595 EUR per person
  • Duration

    10 Days

  • Departure Day(s) and Time(s)

    Contact Guide

  • Starting Location


  • Price Includes

    Two experienced guides, minibus transport, accommodations, meals, drinks, gratuities for hotel porters and waiters, entrance fees, local specialist guiding fees.

  • Notes

    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.


  • The secret of our small group walking tours lies in choosing exciting itineraries and turning them into relaxing vacations for others to enjoy.
  • We offer you the luxury to relax, be carefree and totally immerse yourself in the local atmosphere, making the most of your precious 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.
  • Enjoy visiting the most idilic hilltop town of central Italy, accompanied by fine food & wine.
  • 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.

Trip Info

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.


Day 1
Meet in Cortona (Terontola Station)

Day 2
Chianti wine country & Siena

Day 3
Montepulciano – Monticchiello – Pienza

Day 4
The Abbey of Sant’Antimo – Montalcino

Day 5
Exploring Cortona

Day 6

Day 7
Trevi to Spoleto

Day 8
Mt. Subasio National Park & Assisi

Day 9
Civita di Bagnoregio & Orvieto

Day 10
Departure from Orvieto station

Your adventure awaits!

Caspin Journeys Ltd

We offer small group tours in Italy, England and Spain. For many years we have been escorting travelers who seek that unique experience that blends a hassle-free holiday with the flexibility and independence that reflects their personal wishes. Our insider knowledge of these regions guarantees that as a guest on any of our small group tours of Italy, England or Spain you’ll enjoy all the major highlights along with a selection of off-the-beaten-path and behind-the-scenes experiences that reveal the authentic flavours of your chosen destination.

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