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Best of Chianti

Duration

Total 5 days

Average 4h 38min
Distance

Total 47.1 km

Average 15.7 km
Ascent

Total +1290 m

Average +430 m
Descent

Total -1290 m

Average -430 m

Overview
Itinerary
What's Included
FAQ

> Walk from village to village through Chianti Classico
> Enjoy Tuscan wine and cuisine straight from the source
> We book your boutique stays in Chianti's best towns

Golden hills, old stone farmhouses, and vineyards as far as the eye can see. Tuscany isn't just beautiful, it’s absurdly beautiful. And walking is the best way to drink it all in. On this 5-day trek through Chianti, you’ll go from Greve to Radda to Gaiole, through the heart of Italy’s most iconic wine country. It’s a journey made for food lovers, wine dreamers, and anyone who believes slow travel is the best travel.

This is the shorter version of our full 7-day Chianti route. You’ll cover the most scenic stretches and still get your fill of Tuscan views, tagliatelle, and local vino. The walking is relatively easy and the elevation changes are kind to your knees. Perfect for hikers who want the Chianti experience without the hustle.

Itinerary

Day

1

Arrival in Greve

Welcome to Greve in Chianti, the heart of the Chianti region and the starting point for your week-long adventure. The town’s historic Piazza Matteotti is lined with charming cafés and wine shops, offering the perfect introduction to Tuscan culture. Settle in with a glass of Chianti Classico, take in the relaxed village atmosphere, and enjoy a gentle start to your journey as you prepare for the beautiful walks ahead.

Albergo Casa Al Sole (Greve)

Info

Day

2

Greve - Radda in Chianti

Duration: 05:45 h

Distance: 19 km

Ascent: 720 m

Descent: 430 m

Your day begins in the heart of Greve, with more than half the walk gradually ascending through classic Tuscan countryside. The trail climbs steadily toward Montegonzi, offering sweeping views of the Chianti Hills and the ancient hamlet of Montefioralle.

From there, continue to Panzano in Chianti, a charming village that makes the perfect spot for a mid-hike pause. Grab a coffee, enjoy a light lunch, or simply soak in the scenery before tackling the next stretch.

The trail continues uphill through olive groves and vineyards, leading you over a gentle ridge before a rewarding descent. Surrounded by rolling hills and timeless landscapes, you'll cross a tranquil river valley before facing the final climb up to Radda in Chianti, one of the most picturesque and historically rich villages in the region.

Palazzo Leopoldo Dimora Storica & Spa (Radda in Chianti)

Info

Day

3

Radda in Chianti - San Sano

Duration: 03:40 h

Distance: 12.3 km

Ascent: 290 m

Descent: 440 m

From Radda in Chianti, this stage leads you through classic Chianti countryside towards San Sano. The route is not overly long, but it is varied, with steady changes in height throughout the walk. Leaving Radda in Chianti, the route first heads south with a view back towards the town before descending through the hills. After the lower section, you climb again towards the area around Giardino di Ama and Castello di Ama, where the route passes through a more open landscape with views over Chianti. From there, the trail continues close to Lecchi and follows a gentler line, with small rises and descents before the final approach.

The arrival into San Sano is straightforward, with the route easing down towards the village after the last rolling section. Your accommodation is at the end point, a good place to settle in after a varied walk through vineyards, quiet lanes and hillside tracks.

Agriturismo San Sano (San Sano)

Info

Day

4

San Sano - Ponte a Bozzone - Siena (With Bus)

Duration: 04:30 h

Distance: 15.8 km

Ascent: 280 m

Descent: 420 m

This route ends at Ponte a Bozzone, where you can call it a day and take the bus to Siena. Alternatively, you can follow route option 2, which continues all the way into Siena on foot. From San Sano, this stage leads south through quiet Chianti countryside, with rolling terrain, an early descent and a gradual finish towards the valley.

You leave San Sano on a smaller path during the first kilometres, before joining a wider track that continues south, past the entrance to the Chianti Sculpture Park. From there, you follow paths and quiet lanes through the hills, passing Vallepicciola winery before the route bends towards Villa di Geggiano and Grogno. The final kilometres lead down towards Ponte a Bozzone, where the walking route finishes close to the bus connection for Siena.

At Ponte a Bozzone, you can take the bus into Siena, with a ride of about 30 minutes. Our suggested bus stops are from GEGGIANO, Siena, in Ponte a Bozzone, to PIAZZA INDIPENDENZA, Siena. For current timetables and tickets, visit Autolinee Toscane before you travel.

Siena Vip B&B (Siena)

Info

Day

5

Departure from Siena

After a final morning in beautiful Siena, it’s time to say farewell to Tuscany. You’ll depart with memories of scenic walks, charming villages, and the flavors of Tuscan cuisine—a pilgrimage that connects you deeply with the spirit of Tuscany.

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Contact our Trekking Expert

Jelle Tekstra

Included

Accommodation

We will arrange your accommodation on the Tuscany Experience in hotels, inns, and guesthouses. Accommodation will be private in single, double or twin rooms and with en-suite bathroom where possible.
Full travel guide

You’ll receive access to our trekking app, which serves as your complete digital travel guide for the Tuscany Experience. Inside, you’ll find everything you need for your trek: route descriptions, hiking maps, navigation support, payment information, and all the key details specific to your journey.
Baggage Transfer

This trek includes the transfer of your luggage throughout the entire Tuscany Experience trek. Your bags will be picked up every morning from the hotel lobby and will be driven to your next next accommodation. Baggage transfers allow you to travel lighter during the day and enjoy the walk in a more relaxed manner.
Breakfast

Breakfast is, if possible, included in this trek and it will be provided every morning at your accommodation.
Navigation support

Our trekking app also includes built-in navigation support. With GPS-based maps and offline access, you can follow the trail confidently and stay on route even without mobile signal.

Excluded

Traveling to and from

You have to make your own way to the starting point. The total amount does not include personal transport. This also applies to any transport from the end point of your trail.
Transfers

If you require any form of public or local transport during the trek, it is not included in the package unless stated otherwise. This applies to taxis, buses, cable cars, gondolas, and similar services.
Travel Insurance

Your international travel insurance is your own responsibility. Discuss your itinerary with the insurance company before your trek.
Lunch and Dinner

Breakfast is, if possible, included in the price of the trek. You can get lunch and dinner at the shops, hotels, and restaurants along the way.

FAQ

How to Get To the Starting Point of the Trek
How to Get Back at the End of the Trek
What if the dates I want are not available?
If I book now, can I immediately arrange the rest of my trip?
How do I know if this trek is right for me?
Can meals be adapted to my dietary requirements?

How to Book

Booking
Availability
Cancellation policy

Best of Chianti

Itinerary

Arrival in Greve

Albergo Casa Al Sole (Greve)

Greve - Radda in Chianti

Palazzo Leopoldo Dimora Storica & Spa (Radda in Chianti)

Radda in Chianti - San Sano

Agriturismo San Sano (San Sano)

San Sano - Ponte a Bozzone - Siena (With Bus)

Siena Vip B&B (Siena)

Departure from Siena

Included

Accommodation

Full travel guide

Baggage Transfer

Breakfast

Navigation support

Excluded

Traveling to and from

Transfers

Travel Insurance

Lunch and Dinner

FAQ

How to Get To the Starting Point of the Trek

How to Get Back at the End of the Trek

What if the dates I want are not available?

If I book now, can I immediately arrange the rest of my trip?

How do I know if this trek is right for me?

Can meals be adapted to my dietary requirements?

How to Book

Booking

Availability

Cancellation policy

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