Booking : Tuscany 5-12 april 2022

Cortona, AR, Tuscany, Italia

Caspin Journeys Ltd
  • Twitter verified
3 reviews
Apr 5 - 12, 2022
Group size: 4 - 10
Booking : Tuscany 5-12 april 2022
Cortona, AR, Tuscany, Italia

Caspin Journeys Ltd
  • Twitter verified
3 reviews

Apr 5 - 12, 2022
Group size: 4 - 10

About this trip

This is Caspin Journeys Ltd tour with booking form & payment pages. 

Our walking holiday in Tuscany combines long, leisurely walks along footpaths and Roman roads across undulating hills, with visits to sleepy hamlets and mediaeval towns such as Siena, Cortona and Montepulciano.

We stay in a luxurious yet rustic farmhouse set in the heart of Tuscany's vineyards and olive groves from which we set out each day to discover something new.

This is a gastronomic journey through traditional local dishes: soups such as ribollita; pasta dishes with mushrooms and truffles or good old traditional tomato and meat ragu' sauces with pecorino and aged parmesan cheeses sprinkled on generously; pine nuts, grapes and rosemary are used liberally; enjoy panna-cotta or Cantuccini biscuits dipped in Vin Santo for dessert.

Food goes with wine: Chianti Classico, Vino Nobile, Brunello and Vernaccia are synonymous with the wines coming from Tuscany's sun-drenched slopes. The list is endless and mouthwatering.

The beautiful land of Tuscany has influences from the Etruscans, the Romans and the status seeking Guelphs and Ghibellines. All have left their marks in the architecture of the towns, castles and monasteries.

Tuscany is a garden full of secret wonders, rich in culture and heritage, preserved and treasured by its own people, and just waiting for you to discover it!

Summary Introduction

Small-group walking tour in Tuscany, an enchanting region of Italy. We have selected the very best walks, historic sites, and gastronomic delights. Walks along chalky farm roads; rolling hills that stretch as far as the eye can see; towering cypress trees; fields of vines and poppies and medieval villages perched on hilltops; timeless and unchanged Tuscany, in tune with both its past and present. 

Tour Highlights

Mediaeval 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 breath-taking mediaeval villages

Renaissance Pienza and Montepulciano

Activities - Walking, Hiking

Trip Style - Active, Small group,

Getting out and about on foot is a wonderful way to slow down the pace, relax and get some healthy exercise.

When we walk we see so much more - grape vines, wild flowers, ancient oaks, wheat fields, cypress lined avenues, time resistant hills and valleys. As we stroll through historic hill towns we learn about the culture of ancient people; as we gaze up at immense abbeys and castles we marvel at mans ability to conceive of and construct such monuments.

We travel in small groups of ten setting out each day along the paths of history. One guide does the walking while the other one takes care of logistics - moving luggage, organising dinners, choosing wines, preparing picnic lunches which meet the walkers along the way.

In other words we take care of your every need.

Our aim is to give you a care free vacation, leaving you to absorb the beauty, enjoy the company of like minded travellers and take home memories to share and treasure.

We have tailored the best journeys in Italy, England, Spain or Corsica travelling in small groups with like-minded people and we take care of the logistics so that you can relax and be immersed in the culture.

Are you traveling solo? Join us and feel included and welcome on a journey with like-minded travellers.

Contact us if you need more information and we will be happy to answer all your questions 

Interests - Art, Culture, History, Food

We are not ‘Big & Famous’ but we offer top quality and a personal touch.  For over 20 years our family has been accompanying travelers from around the world on authentic and unique travel experiences. We simplify the booking process, harness insider knowledge and share the most incredible adventures ever.  The itineraries we offer you are the fruit of careful research and direct experiences, personally lived by our guides before creating a unique Journey to propose to you.

We are the best researchers of Authenticity, Culture & Traditions in our journeys.


With Caspin Journeys you capture emotions, flavours, fragrances and views above and beyond your expectations.

Recommended for active travelers any age

Group size minimum - 6

Group size maximum - 10

Bigger groups, clubs, alumni please contact us.

Difficulty - Fairly Easy to Moderate

All Caspin Journeys tours can be enjoyed by a wide variety of active people with general good health. We pace each day perfectly so that there is time for everyone to enjoy it and not feel under pressure. We encounter a variety of terrain from wide gravel paths, to narrow, rocky trails and gradients vary too. On our more strenuous tours, there are often two levels of the walk from which to choose. Some people walk at a faster pace while others like to chat or take photographs. Some people do well on the ups while others prefer the downs. You may be ahead on the trail in the morning and enjoying strolling at the back later on!

Easy, Fairly Easy, Moderate, Challenging, Strenuous - more details

Useful links

Special diets catered for

This tour offers Vegetarian and Vegan food options on request. Simply let us know the food option that you prefer.

Languages tour is operated in - English

Cancellation Policy - summary


We incur costs in canceling your travel arrangements, so If you cancel your tour the cancellation charges are as follows:

More than 75 days prior to tour start:   cancellation fee per person  = 25% of tour price

75 - 31 days prior to tour start:   cancellation fee per person =   50% of tour price

Less than 30 days prior to tour start: no refund

For full details please refer to our terms and conditions at his link

Note: It is a requirement of booking with Caspin Journeys Ltd that you have adequate personal travel insurance to cover the eventualities of your trip.

What’s included

  • Tour Leaders
    Owner Guided. Fully Guided: 2 experienced Caspin Journeys Tour Leaders/guides 24/7 Service of expert multilingual Caspin Journeys Leaders/ guides with extraordinary local knowledge.
  • Minibus transport
    From pick-up to drop-off points and during the tour
  • Accommodations
    7 Nights at a luxuriously restored and elegant 17th century Farmhouse Villa ideally located for exploring Tuscany
  • Water
    Water is carried in support vehicle for daily refills
  • Meals
    Typical food of the area! We set the menu for you so that you can have a 360° taste of all the food of the regions 7 Breakfasts, 6 Lunches 7 Dinners
  • Beverages
    Wine, tap water & coffee with meals (no spirits)
  • Local Taxes
    Tourist taxes at hotels
  • Entrance fees
    To museums, events and parks as listed in the itinerary
  • Walking stick
    1 per person
  • Specialist guides
    We use local experts for specialist sites
  • Tipping & Gratuities
    hotel porters & waiters
  • Flights
    travel before and after the tour is not included
  • Train, bus, taxi service
    transport before pick-up & after drop-off
  • Travel insurance
    N.B. It is a requirement of booking with Caspin Journeys Ltd that you have adequate personal travel insurance to cover the eventualities of your trip.
  • Entry visas & clearance
    Valid passport (at least 6 months). Visas are required for travel to certain countries and must be arranged far in advance of departure. It is your responsibility to check the requirements.
  • Minibar & Bar drinks
    Please do not forget to settle your bill before leaving each hotel.
  • Telephone
  • Tipping & Gratuities
    Tipping for your tour leaders is at your discretion.

Available Packages

Number of participants
10 left
Deposit: €656
1 participant, sharing with a friend
10 left

 Booking and paying individually 

Deposit: €656
1 participant, solo traveller
only 2 left

Double room, single occupancy

Deposit: €656


Day 1
Meet at Pisa airport to travel to Cortona

We meet you at Pisa International airport at 14.00. From there it takes us about 2.5 hrs to drive to Cortona where we will check into the farmhouse to relax and unwind. Over an apéritif, we get to know each other in the gardens of the villa. After a briefing on the week's activities, we can all sit down to a traditional home-made dinner with fresh pasta and sauce, Tuscan wine, and a delicious dessert.

Your Organizer

Caspin Journeys Ltd
3 reviews
Journeys for people with a passion for the outdoors, history and culture, gourmet food & wine. We like to think of our guests as travelers, not tourists. Our groups are small and the people are like-minded. We personally research each exciting itinerary and we take care of all the arrangements so you maximize your time & enjoyment. Tours last a week to 13 days. We explore on foot and off the beaten track in order to immerse you in the local culture and tradition and culture in a unique way - the Caspin way!


Like travelling with my family. The Nobiles are utterly charming people who are passionate about what they do. The whole holiday was seemless. There was a mix of cultural activities, walking, staying in exceptional hotels, eating wonderful food, sightseeing and tasting local wines. We travelled everywhere in comfort and of course, appreciated the magnificent scenery.
By Tricia R for Booking : Amalfi Coast 11-18 Oct 2021 on 21 Oct, 2021
It was a fabulous trip and I loved the Puglia and Matera area hikes!!!! So nice to see you both
By Krista H for Private group: Puglia & Matera 26 Sept 2021 on 12 Oct, 2021
Had a terrific time. Pino and Caroline curated a wonderful walking itinerary that included so many things we likely never would have discovered on our own, as well as experiences and interactions that only come from deep knowledge and love of an area. The tour was a nice mix of exploring ancient towns and villages, learning history and hearings stories, and walking through beautiful countryside. Lodgings were first class, meals delicious, and our fellow travelers were great. Highly recommend.
By Phyllis S for Booking : Puglia & Matera 03-10 Oct. 2021 on 12 Oct, 2021