- View all
Best price guarantee Learn More
- Operator
- Caspin Journeys
- Hiking & Trekking
- Epic trails and breathtaking landscapes await
- Group Tour
- Join a group and forge lifelong friendships
- Fully Guided
- An experienced guide will be with you for the entire tour
- Guided in English
- Group Size 6 - 10
- Age range 25 to 82

Highlights
- Medieval Siena, home of the famous Palio horse race.
- Etruscan Cortona and San Quirico D'Orcia.
- Vino Nobile di Montepulciano — Hill towns and delicious wine.
- Natural hot springs at Bagno Vignoni.
- Wellness Thermal Spa visit.
- Monte Oliveto Monastery with frescoed cloister. Ochre-tinged, Crete Senesi hills.
- Rolling landscapes, brilliant light and breathtaking mediaeval villages.
- Renaissance Pienza and Montepulciano
Itinerary
- Introduction
- Day 1 Cortona
- Day 2 A walk in the footsteps of the Etruscans and Saint Francis
- Day 3 A walk between the hill towns of Montepulciano and Monticchiello
- Day 4 Siena and Hot thermal springs
- Day 5 Exploring the hills of Cortona; MAEC museum
- Day 6 Walking the scenic Val D'Orcia from Pienza to Bagno Vignoni
- Day 7 Abbey of Monte Oliveto and its artistic Treasures
- Day 8 Departure
What's Included
- Accommodation
- Insurance
- Meals
- Additional Services
- Transport
- Free eSIMTourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.
What's Not Included
- Flights
- Guide
- Optional
- Additional Services
Adventure Type
- Group AdventuresJoin a group and forge lifelong friendships.What to expect
- Group of 10 travelers max.
- Fast booking confirmation
- Carefully planned itineraries
- Travel with like-minded people
- Personalized AdventuresCustomize an existing itinerary or create your own.What to expect
- Travel with your own group of min. 6 travelers
- Choose your preferred dates and duration
- Upgrade your accommodation
- Customize the itineraries

Operated by
Caspin Journeys
Number of tours
17
Age Range
25 to 80 years old
Response time
within 1 day
Response rate
100%
Our journeys are for people who have a passion for the Outdoors, History and...
Read moreCustomer Reviews
- Overall RatingExcellent
- ItineraryExcellent
- GuideExcellent
- TransportExcellent
- AccommodationExcellent
- FoodExcellent
- KLKen· October 5th, 2024I can't say enough about Caspin Journeys. The hosts were wonderful and made us feel like family right away. So well organized and planned out. The views were incredible along the way and even though there was a lot of walking, the pace was comfortable. Every detail was planned perfectly. The food was outstanding, and the small group size made it easy to get to know everyone. Would definitely recommend this tour company to anyone thinking of going to Europe.Show moreTrip date: September 2024
Dates & Availability
Why book with TourRadar?
- Trusted and vetted operators
- Rated excellent on
- Best price guarantee
- 24/7 customer support
- Earn $100 in travel credits
- Free eSim with every purchase
To protect your payment and ensure your booking will be processed in Australia, never transfer or communicate outside of the TourRadar website or app.
- From Wednesday24 Sep, 2025To Wednesday1 Oct, 2025From:$6,717
- Instant ConfirmationFrom Monday18 May, 2026To Monday25 May, 2026EnglishMultiple Room TypesFrom:$7,005
Best price guarantee Learn More
What our customers ask about this tour
The content in our FAQ section is subject to change.- S
Samuel
Asked on September 17th, 2022If this is a walking tour, what happens when it's raining? Umbrellas or different transport?
- Caspin JourneysOperator•Written September 2022
When it rains on a walking/hiking tour we put on a waterproof and walk anyway.
- J
Jordan
Asked on March 23rd, 2022Must I pay single supplement if travelling alone or is there the option of room share with same gender person?
- Caspin JourneysOperator•Written March 2022
We are a family run company and are always happy to welcome single women into our small groups. We don't have a system for pairing up people automatically and so if we get two people asking for a buddy, we put them in touch with one another and they decide if they want to share. If not, they obviously need to be ready to pay a single supplement if they want to come on the tour.
- H
Hayley
Asked on February 2nd, 2022My sister and I are looking to do a Tuscany and Amalfi Coast tour in 2023. I am very interested in your walking tours, they look wonderful! Can you give me some information on how we can do both of these tours?
- Caspin JourneysOperator•Written February 2022
Combining Tuscany and Amalfi in one go is tricky because there is a big gap of time in between them and you would have to fill it! We run all our own tours, so we don't have lots of departures going for each tour during the year. However, if you can find two back-to-back Caspin tours which take your fancy then we would give you a 10% discount on the cheaper one of the two!
Good to Know
Tour ID: 209940
Similar Tours
Keep Exploring Italy
- Hiking in Europe in May
- Luxury River Cruises & Cruise Lines
- 10 Best Hiking & Trekking Companies
- Your Guide to Planning a Private Hike 2025/2026
- Italy Hiking & Trekking
- Small group tour
- 8 days Italy
- Operators in Europe
- Tuscany
- Tuscany Walking & Hiking Tour Tours in Italy
- Hiking & Trekking Tours
- Italy Tours
- Hiking & Trekking Tours
- Group Tours
- Fully Guided Tours
- Explorer Tours
- Central Italy