Tuscany walking and hiking

from
 2,500 1,995

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


  • Reviews 0 Reviews
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  • Vacation Style Holiday Type
    Food and Wine, Walking & Hiking
  • Activity Level Leisurely
    1/8
  • Group Size Small Group
    10
All about the Tuscany walking and hiking.

Tramping Through Tuscany!

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!

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.

  • Tour Leaders – 24/7
  • Minibus transport – From pick-up to drop-off points and during the tour
  • Accommodations – as listed in the itinerary in double or twin bedrooms, double occupancy.
  • Water – Carried in the support vehicle for daily refills
  • Meals – as per the itinerary
  • 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
What is not included in this tour?Items that are not included in the cost of tour price.
  • Flights – travel before and after the tour is not included
  • Train, bus, taxi service – transport before pick-up & after drop-off
  • Travel insurance – 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.
  1. Day 1 Pisa airport 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.

  2. Day 2 Exploring the hills around Cortona

    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

  3. Day 3 A walk between two Tuscan hill towns - The full Monti!

    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

  4. Day 4 Siena & Hot Thermal Springs

    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.

  5. Day 5 A walk in the footsteps of the Etruscans and Saint Francis

    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

  6. Day 6 Walking in the Scenic Val D'Orcia
    We journey to Pienza, famous for Pecorino cheese and Renaissance architecture. The town of Pienza was built in 1458 on top of the old village of Corsignano at the request of Pope Pio II Piccolomini as a symbol of the Italian Renaissance.
    From the walls of the city, you get some of the most beautiful views in Tuscany -the breathtaking Orcia valley, immortalized in 2000 in the Gladiator film. From here we step out into its rolling hills with the walls and towers of the medieval village of San Quirico D’Orcia beckoning us.
    We are now on the Via Francigena, which has seen the passage of pilgrims and popes, knights and mercenaries, kings and emperors. All have walked the same country lanes and woodland tracks to reach the mineral-rich waters at Bagno Vignoni and bathe in its hot pools of bubbling volcanic water.
    Fancy dipping your feet in? No problem!
    Walking time: 3-4 hours Distance 12 km (7.5 miles) Ascent +150 hm Descent 250 hm
  7. Day 7 Abbey of Monte Oliveto and its artistic treasures

    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

  8. Day 8 Departure day

    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)

andalusia-spain-jamon-small-group-walking-tour-caspin-journeys
Accommodation

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

molino-di-bordone-cooking-tour-with-local-chef-caspin-journey
Molino di Bordone

Cooking Class Kitchen
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