9.30 Drop off at Chiusi-Chianciano Terme station with direct trains for Rome and Florence.
Meals: Breakfast
8 DAYS • 7 NIGHTS
GROUP SIZE: 8 – 12
activity level: MODERATE
FROM € 3,900
DATES & AVAILABILITY
07 – 14 June 2027
PRIVATE GROUP
CHECK AVAILABILITY FOR OTHER DESTINATIONS
FOR PRIVATE GROUPS OR OTHER INFO
Our Tuscany walking tour 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 traditional, yet luxurious, country farmhouse set in the heart of Tuscany’s vineyards and olive groves, which serves as our home base as we set out each day to discover something new. This is a gastronomic journey through traditional local dishes — hearty ribollita, fresh pasta with truffles, and aged pecorino cheese — all paired with the region’s celebrated wines.
Tuscany is a garden of secret wonders, rich in heritage and preserved for the delight of today’s travellers.
Our Tuscany walking tour explores Italy’s Renaissance heart, leading you through rolling vineyards, ancient Roman roads, and medieval hamlets. From the sculptural Val d’Orcia to the stone streets of Siena and Cortona, this journey celebrates the harmonious blend of heritage and stunning scenery.
PICK UP: 15.30 Terontola Cortona train station (on the direct train line from Rome & Florence).
DROP OFF: 9.30 Chiusi-chianciano Terme station.
Before the tour starts, we recommend you spend a few days in the beautiful city of Florence, the birthplace of the Renaissance and UNESCO world heritage site.
We meet at Terontola-Cortona train station at 15.30 and drive to our local cafe’. From here we can walk the short distance to the farmhouse, your home for the week while the luggage goes ahead.
Time now to relax, unpack and get to know each other in the gardens with a drinks party before dinner.
Meals: Dinner
Walk: 30 minutes; 2km
Overnight: Cortona
We visit Cortona’s monumental Etruscan burial tombs and learn more about the ancient practices of this ancient culture. 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.
Meals: Breakfast / Lunch / Dinner
Hike: 12 km (7.5 miles), Ascent +310 m Descent 150 m, 3/4hrs
Overnight: Cortona
Our walk today connects the fortified hilltop towns of Monticchiello and Montepulciano via scenic trails through vineyards, olive groves, and oak forests. We approach via the iconic zigzag cypress-lined road—a staple of Tuscan imagery often featured in movies.
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 right up until the second world war! Allow yourself to be cast back in time as you explore the narrow streets, the ruined towers, and pop your head inside the 13th-century gothic church to see Lorenzetti’s alter piece.
We then head to bustling Montepulciano where a single winding street climbs up to a charming main square, which crowns the summit with a circle of civic buildings and a town hall reminiscent of Florence.
Meals: Breakfast, Lunch & Dinner
Hike: 9.5 km (6 miles) Ascent +250m, 3 hours
Overnight: Cortona
While Siena’s origins delve into the Etruscan and Roman past, it remains one of the most breathtakingly complete medieval cities in the world. Within its imposing walls, the city is dominated by the Palazzo Pubblico—with a tower that seems to touch the sky—and the magnificent, scallop-shaped Piazza del Campo, where the thundering hooves of the Palio horse race echo twice a year.
We’ll join a local guide for a historic walk through the ages to see one of the most richly decorated cathedrals in the world, home to treasures by Donatello and Michelangelo.
After free time for lunch, we head to the healing waters of Rapolano Terme to relax and swim while enjoying unique views of Tuscany at sunset. Refreshed, we’ll gather for an evening passeggiata—the classic Italian stroll—before enjoying dinner at a local restaurant.
Meals: Breakfast, Dinner
Walk: City walking tour 2 hrs
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.
Meals: Breakfast, Lunch & Dinner
Hike: 9.5 km (6miles) Ascent +300m, 3hrs
Overnight: Cortona
We journey to Pienza, famous for Pecorino cheese and Renaissance architecture. The town of Pienza was built in 1458 at the request of Pope Pio II 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 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!
Meals: Breakfast, Lunch & Dinner
Hike: 12 km (7.5 miles) +/- 200m, 3-4hrs
Overnight: Bagno Vignoni
A spectacular drive into the Crete Senesi takes us to the fortified village of San Giovanni d’Asso where we begin a scenic walk that gives us plenty of time to admire the contrasts in this unusual and desolate landscape of ochre-colored hills. When we reach Monte Oliveto we enjoy a picnic lunch and visit the abbey to see the beautiful frescoes in the cloisters. These were painted by Renaissance artists Sodoma and Signorelli tell the story of the life of Saint Benedict.
Meals: Breakfast, Lunch & Dinner
Hike: 10 km (6 miles), +200m, 3hrs
Overnight: Bagno Vignoni
8 DAYS • 7 NIGHTS
GROUP SIZE: 8 – 12
activity level: MODERATE
FROM € 3,900
DATES & AVAILABILITY
7 – 14 June 2027
PRIVATE GROUP
CHECK AVAILABILITY FOR OTHER DESTINATIONS
FOR PRIVATE GROUPS OR OTHER INFO
Our Tuscany walking tour is a quintessential journey through a garden of secret wonders. We offer a unique blend of high culture and natural beauty, transitioning between medieval hamlets like Cortona and Montepulciano and the iconic, UNESCO-listed landscapes of the Val d’Orcia. Rather than moving every day, we use Molino di Bordone, a traditional and high-quality restored restored watermill set amongst olive groves as our home base. This allows for a true gastronomic journey through traditional local dishes like fresh pasta with truffles and aged pecorino cheese, all paired with the region’s celebrated wines.
We meet at 14.00 on Day 1 at the Terontola-Cortona Train Station. This location is easily accessible as it sits on the direct train line connecting both Rome and Florence.
By Air: International travellers should fly into Florence (FLR) or Rome Fiumicino (FCO). From these cities, you can take a direct train to the Terontola-Cortona station, making the transfer to our meeting point straightforward and easy. Use trenitalia.it if you want to book train tickets in advance.
We highly recommend spending some time in Florence before the tour begins, to adjust to the time zone and explore the “birthplace of the Renaissance”.
We rate this tour as Moderate, featuring leisurely walks and hikes across undulating hills. You should be prepared to walk between 2km and 12km (1.2 to 7.5 miles) per day, with manageable elevation gains typically ranging from +200m to +310m. The terrain includes a variety of surfaces such as gravel and dirt tracks, ancient Roman basalt tracks, and narrow medieval town streets.
Read more on our Difficulty Level Guide.
Tuscany is a world-class gastronomic destination, and our tour celebrates authentic local flavours. You will enjoy traditional dishes such as hearty ribollita, fresh pasta with truffles, and aged pecorino cheese from Pienza. These “Tuscan feasts” are expertly paired with the region’s celebrated wines from Montepulciano, Montalcino and the surrounding vineyards.
We stay at Molino di Bordone, a traditional, high-quality country farmhouse. This beautifully restored watermill is set in the heart of Tuscany’s olive groves and serves as our private base for the week. This allows you to relax and unpack just once and truly enjoy your new home for the week.
We schedule our tours to take advantage of the most temperate seasons. In Spring, the hills of the Val d’Orcia are incredibly lush and green, with mild temperatures perfect for exploring. In Autumn, you can experience the harvest season, which offers crisp air, vibrant colours, and the ideal time to sample fresh olive oils and truffles.
Sturdy, well-broken-in walking boots are essential for the varied terrain and ancient stone tracks. We recommend a layering system including lightweight base layers, a warm fleece, and a high-quality waterproof jacket for changeable weather. While generally relaxed, smart-casual attire is ideal for our evening dinners and the local passeggiata. Always pack a sun hat, high-factor sunscreen, and a refillable water bottle.
How do I book this tour with Caspin Journeys?
To book, click on the BOOK NOW button next to your preferred departure date on our website or contact us via inquiries@caspin.com
A deposit reserves your spot, and the balance is due ahead of the tour.
Is travel insurance required?
Yes. All participants must have comprehensive travel insurance that covers medical emergencies, trip cancellation, evacuation, and loss/damage of personal items.
Can I join as a solo traveller?
Yes — solo travellers are welcome. In the moment of booking, choose the single room option.
What about tips?
This question comes up a lot. Tips and gratuities for most services during the trip such as restaurant staff, porters etc. are included and handled by Caspin Journeys.
As for your tour leaders we at Caspin leave this gesture to your discretion.
If you have already booked to travel with us,
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