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2026

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Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Tuscany Walking & Hiking Tour

8 days
Start and end in Cortona
5.0
1 traveler review

No departure dates available

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Plan your adventure:
Hiking & Trekking
Epic trails and breathtaking landscapes await
Fully Guided
An experienced guide will be with you for the entire tour
Medium Intensity
Travelers should be comfortable with somewhat-demanding activities
Guided in English
Group Size 6 - 10
Ages 25+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Terontola-Cortona to Cortona

    Start point
    Stazione Terontola-Cortona, Località Landrucci, 124, Cortona, Arezzo 52044, Italy (Terontola Train Station, 14:00)
    Meals
    Dinner

    Included Activities

    • Transfer from Terontola-Cortona train station to local cafe
    • Walk to farmhouse
    Landmarks
    Terontola-Cortona Station
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  2. Day 2

    Cortona

    Meals
    Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner

    Included Activities

    • Visit Etruscan burial tombs
    • Hiking trail on Monte Egidio lower southern flank
    • Exploration of Hermitage of Saint Francis
    • Guided tour through Cortona
    Landmarks
    Etruscan Burial Tombs
    Monte Egidio
    Hermitage of Saint Francis
    Cortona
  3. Day 3

    Montepulciano

    Meals
    Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner

    Included Activities

    • Walk through Monticchiello
    • Exploration of Monticchiello fortress and towers
    • Visit to 13th-century gothic church
    • Walk to Montepulciano
    • Exploration of Piazza Grande
    Landmarks
    Monticchiello
    Montepulciano
    Piazza Grande
    Itinerary Image 1Itinerary Image 2
  4. Day 4

    Rapolano Terme

    Meals
    Breakfast, Dinner (Dinner at a local restaurant)

    Included Activities

    • Historic city walking tour of Siena with local guide
    • Visit to Siena Cathedral
    • Thermal bath experience at Rapolano Terme
    • Evening passeggiata and dinner at local restaurant

    Optional Activities

    • Museum visits in Siena
    • Lunch in Siena
    Landmarks
    Siena
    Il Campo
    Siena Cathedral
    Palazzo Pubblico
    Rapolano Terme
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Cortona

    Meals
    Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner

    Included Activities

    • Walking from farmhouse to Cortona
    • Exploration of Cortona via ancient city gates
    • Guided visit to Etruscan museum

    Optional Activities

    • Gelato or cappuccino at local cafes
    Landmarks
    Cortona
    Etruscan Museum
  6. Day 6

    San Quirico d'Orcia - Bagno Vignoni

    Meals
    Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner

    Included Activities

    • Visit to Pienza
    • Walk to San Quirico d'Orcia
    • Walk along the Via Francigena
    • Access to Bagno Vignoni hot pools

    Optional Activities

    • Dipping feet in Bagno Vignoni hot pools
    Landmarks
    Pienza
    Orcia Valley
    San Quirico d'Orcia
    Bagno Vignoni
    Via Francigena
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  7. Day 7

    Abbey - Buonconvento

    Meals
    Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner

    Included Activities

    • Drive through Crete Senesi
    • Visit to abbey with Renaissance frescoes
    • Scenic walk through Crete Senesi landscape
    • Visit to Buonconvento

    Optional Activities

    • Gelato in Buonconvento
    Landmarks
    Crete Senesi
    Buonconvento
    Itinerary Image 1
  8. Day 8

    Terontola-Cortona Departure

    End point
    Stazione Terontola-Cortona, Località Landrucci, 124, Cortona, Arezzo 52044, Italy (Terontola Train Station, 10:00)
    Meals
    Breakfast

    Included Activities

    • Transfer to Terontola-Cortona station
    Landmarks
    Terontola-Cortona Station

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What's Included

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  • Accommodation
  • Insurance
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights
  • Guide
  • Optional
  • Additional Services

Operated by

Caspin Journeys

Rating
5(138 reviews)
Response time
9 hours
Response rate
100%
Cancellation policy

Traveler Reviews

5.0
Overall rating based on 1 Reviews
  • Itinerary
    5.0
  • Transport
    5.0
  • Guide
    5.0
  • Accommodation
    5.0
  • Food
    5.0
  • 5.0

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  • K
    October 5th, 2024
    I can't say enough about Caspin Journeys. The hosts were wonderful and made us feel like family right away. So well...
    Show more
    Traveled in September 2024

What our customers ask about this tour

The content in our FAQ section is subject to change.
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Try a different search term or ask a question to this adventure's experts
  • S

    Samuel

    Asked on September 17th, 2022

    If this is a walking tour, what happens when it's raining? Umbrellas or different transport?

    Tour Details
    • Caspin JourneysOperatorWritten September 2022

      When it rains on a walking/hiking tour we put on a waterproof and walk anyway.

  • J

    Jordan

    Asked on March 23rd, 2022

    Must I pay single supplement if travelling alone or is there the option of room share with same gender person?

    Accommodation
    Single supplement
    • Caspin JourneysOperatorWritten 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, 2022

    My 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?

    Operator
    Tour Details
    • Caspin JourneysOperatorWritten 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!

Can’t find the answer to your question?
Reach out to the experts at Caspin Journeys with your enquiry, they usually respond within 9 hours.

No departure dates available

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Good to Know

Tour ID: 209940

  • Currency
    Euro
    Italy
  • Plugs & Adapters

    As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for type L.

    Type L
    Italy
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before August 12th, 2026 a full payment is necessary. For tours departing after August 12th, 2026, a minimum payment of 25% is required to confirm your booking with Caspin Journeys. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 80 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Caspin Journeys will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Caspin Journeys" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec