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Our walking holiday in Tuscany combines long, leisurely walks along footpaths and Roman roads across undulating hills, with visits to sleepy hamlets and medieval 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 pannacotta 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!
SCHEDULED DATES
5 – 12 April 2022 > – contact us
24 – 31 March 2023 > – contact us
4 – 11 Nov 2023 > – contact us
DURATION: 8 days
PICK UP: Pisa airport
DROP OFF: Pisa airport
Small-group walking tour in Tuscany, an enchanting region of Italy. The 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.
Walking holiday combining leisurely walks along footpaths, and Roman roads across undulating hills, with visits to sleepy hamlets and mediaeval towns such as Siena, Cortona, and Montepulciano. Along the way, we find frescoes by famous painters still in their original settings. 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. So there’s no need to pack and unpack luggage once we have arrived!
In Tuscany, we make a gastronomic journey through traditional local dishes. The biggest influence on Tuscan cooking has been simple peasant cooking: we savour soups such as ribollita; pasta dishes with mushrooms and truffles or the good old traditional tomato and meat ragu’ sauces with pecorino and aged parmesan cheeses sprinkled on generously; fruits of the land such as pine nuts, grapes and rosemary are used liberally; enjoy pannacotta or Cantuccini biscuits dipped in Vin Santo for dessert. The list is endless and mouthwatering.
Food in Italy goes with wine and Tuscany always sparks off ideas of Chianti in a straw-covered flask; The famous Chianti Classico, Vino Nobile, Brunello, and Vernaccia are synonymous with the wines coming from Tuscany’s sun-drenched slopes. We will also be introducing you to some less well-known names with pleasant surprises.
The beautiful land of Tuscany has influences from the Etruscans, the Romans, and the status-seeking Guelphs and Ghibellines. All these people have left their marks in the architecture of the towns, castles and monasteries which dominate the skyline in all directions. Tuscany is a man-made garden full of secret wonders. Rich in culture and heritage, preserved and treasured by its own people, it is just waiting for you to discover it!
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.
We set out on foot from our farmhouse and head into the hills to walk gently up the hill to Cortona passing through tiny hamlets of stone houses, walking along ancient Roman basalt tracks, and through olive groves.
We enter Cortona via one of the ancient city gates and wind along narrow streets of fascinating historic monuments. After lunch, we visit the Etruscan museum with a guide, and then there is free time to indulge in a gelato or sit with a cappuccino in a café.
Walking time: 3 hours Distance 9.5 km (6miles) Ascent +300 hm
The two fortified medieval walled hill towns of Monticchiello and Montepulciano stand at over 500 and 600 meters and are connected by trails through extensive farmland of vines, olives, and oak forests. A great walk with lots of exploring and history!
Our first approach is from the famous zigzag cypress-lined road featured on the cover of brochures and television advertisements! Monticchiello feels very sleepy today with its pretty flower gardens, but during its 800-year-old history
Monticchiello was often the object of wars and assaults, destruction and occupations, right up until the second world war! Allow yourself to be cast back in time as you explore the narrow streets, the fortress and ruined towers, and pop your head inside the 13th-century gothic church to see Lorenzetti’s Madonna con Bambino alter piece.
Montepulciano on the other hand is a bustling little city with one winding street (1.5kn) that climbs up to a charming main square, (Piazza Grande) which crowns the summit with a circle of civic buildings and a town hall reminiscent of the Palazzo Vecchio of Florence.
Walking time: 3 hours Distance 9.5 km (6 miles) Ascent +250 hm Descent 150hm
Siena has origins that delve deeply into the Etruscan and Roman past, but what we see here is the most beautiful and completely medieval cities in the world. It has imposing city walls, a Palazzo Pubblico with a tower that almost touches the sky, and a scallop-shaped main square, Il Campo where the famous Palio horse race runs every year. Our local guide will deftly take you on a historic city walk through the ages and to one of the most beautiful cathedrals in the world. After free time to have lunch, look around and visit museums we then head to the hot thermal baths of Rapolano Terme to relax and swim in these healing waters and enjoy unique views of Tuscany at sunset. Change ready to enjoy an evening stroll (the Italian Passeggiata) and dinner in a local restaurant.
We visit Cortona’s monumental Etruscan burial tombs and learn more about the ancient practices of the Etruscan culture and its impact on the territory. Our hiking trail lies on the lower southern flank of Monte Egidio and follows gravel and dirt tracks past streams, stone houses, olive groves, and through oak forests. Evidence of Cortona’s farming traditions over a span of 2000 years is gradually revealed. We stop to explore the tranquil 12th century Hermitage of Saint Francis and then continue to the town Cortona itself.
Walking time: 3-4 hours Distance 12 km (7.5 miles) Ascent +310 hm Descent 150 hm
A spectacular drive through the Crete Senesi takes us to the abbey. The beautiful frescoes in the cloisters, painted by Renaissance artists, Sodoma and Signorelli tell the story of the life of Saint Benedict.
Our scenic walk gives us plenty of time to admire the contrasts in this unusual and rather desolate landscape of ochre-colored hills. We arrive at the walled village of Buonconvento to enjoy a gelato and think about the pilgrims on the Via Francigena who stopped to rest here on their way to Rome.
Walking time: 4-5 hours Distance 16 km (10 miles) Ascent +100 hm Descent 340 hm
Two options: Drop off at the local station of Terontola with direct trains for Rome and Florence (10 mins away). Drop off at Pisa airport (2.5-3 hours away)
A nice hotel and a good night’s sleep are an important part of your overall travel experience!
When considering a hotel, we look at more than just the rooms. We look for hotels or bed and breakfasts which are committed to ensuring their guests are well looked after and pay attention to detail, for example offering locally sourced breakfast produce, or a special selection of toiletries, or tea and coffee making facilities in the room. Wherever possible your hotel* will be perfectly positioned for exploring and will have a historical charm or maybe a new and innovative design. We choose the best possible places to stay ensuring that each night you are comfortably settled in a place that is welcoming and full of authentic local charm. We are on a mission to find the ingredients you need to wake up feeling rested and looking forward to each day of your Caspin Journeys tour!
Take a closer look at some of the places we have chosen for you…
7 Nights at a luxuriously restored and elegant 17th century Farmhouse Villa ideally located for exploring Tuscany.
Molino di Bordone is authentically restored, furnished with country charm and decorated with the utmost attention to detail. Pino and Caroline Nobile restored this old Tuscan Mill from a ruin that had been empty for over 30 years. They were drawn by the peacefulness of the place and fell in love with its 360 degree views of the surrounding vineyards and olive groves.
*Hotels may vary
Frequently Asked Questions (FAQs)
We love our jobs and personally lead all our small group tours. Italy, Spain and England are our homes and our passion. We bring that excitement with us on all our tours so that you too share our favourite places.
We are very experienced and handle all the logistics while you relax and become immersed in the local culture, history and traditions.
We know the locals on all our trips and they love meeting our groups. We are small enough to get into private homes, chat to villagers, fit in small restaurants and enjoy all kinds of unexpected events that aren’t accessible to large groups of tourists following a red umbrella.
Our customer reviews say that Caspin Journeys takes the best care of you. We are a sustainable travel company and the only thing we leave behind is our footprints!
Read more about Caspin >
We believe that where you sleep is an important part of your overall travel experience. So we put a lot of effort into carefully choosing the hotels for each tour.
We always look for attractive, clean and quiet rooms with private bathrooms. But, our priority is also to find the best possible accommodations to make sure that each night you are comfortably settled in a place that is welcoming and full of authentic local charm.
The result is a fabulous selection of delightful hotels, medieval palaces, family-run hotels, country residences, manor houses, historic inns, luxurious alpine hotels – sometimes with a spa, sauna or swimming pool facilities – and all with character, good food and a friendly atmosphere.
You will have to keep coming back to experience them all! Sweet Dreams!
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 – grapevines, wildflowers, ancient oaks, wheat fields, avenues of cypresses and pine, time resistant hills and valleys.
As we stroll through historic towns we learn about the culture of the people; as we stand in the splendour of the countryside, beneath the soaring columns of ancient temples, abbey walls and turrets of medieval castles we marvel at man’s ability to conceive of and construct such monuments.
Food is an all important part of each and every one of our journeys. We are foodies, we love to savour the authentic flavours of each destination we visit. And let’s not forget the wine “the drink of the gods” which will accompany every meal, even picnics!
Picture yourself eating Buffalo mozzarella from a farm in Amalfi, tasting a Sicilian cannolo with fresh ricotta cheese, home-made pasta, organic vegetables, fresh fish and so on.
Or why not consider a Gourmet Cooking Holiday in Tuscany, where you will learn directly from the locals?
If all this sounds mouthwatering then look no further, you are in the right place 😉
On our small group tours we use a combination of gourmet restaurants, local trattorias, traditional pubs, tapas bars and farmhouse meals, to give you the best overall experience!
Each adventure combines fantastic hikes and authentic cultural experiences which make for a phenomenal and enriching travel experience. – admire Giotto’s frescoes in Assisi – walk in the Castle gardens of Henry VIII – stand at the tomb of St James in Compostela – gaze at and touch the columns of a Greek temple – visit the birthplace of Napoleon Buonaparte – see how a Duke lives at Blenheim Palace – tread the streets of Pompeii – admire mosaics in a Norman cathedral – understand more about the Roman Empire Travel in the richest artistic heritage in the world, many of which are part of UNESCO. What are you waiting for? Don’t miss out on an unforgettable trip.
Our travel style attracts a similar type of people, outgoing, interesting, adventurous, cultured and curious.
You’ll enjoy the company of your fellow travelers on our small group tours. Italy’s food and wine, England’s local pubs, and Spain’s meditative and spiritual pilgrim route are best experienced amidst the camaraderie of the group.
Guests who join our small group tours become our friends. They return again and again to share new adventures as we explore these unforgettable destinations with like-minded travellers and build ever-lasting memories together.
