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Best of Chianti

Name: Best of Chianti
Brand: Bookatrekking
Price: 695.00 EUR
Availability: InStock
Rating: 4.4 (1611 reviews)

Duration: 5 days

Trails: T1 trails

Distance: 15 - 20 km per day

Ascent per day: 500 - 1000 m ascent per day

Available in September

Available in October

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

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

Info

Day

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

Info

Day

Radda – Gaiole in Chianti

Duration: 03:50 h

Distance: 12.9 km

Ascent: 400 m

Descent: 430 m

Today's stage is more varied, with a mix of forest paths and open fields, offering both shaded trails and panoramic views of the Chianti hills. As you walk, you’ll pass quiet valleys and peaceful woodland paths, allowing you to fully immerse yourself in the tranquil beauty of Tuscany. Your destination, Gaiole in Chianti, is famous as the starting point of the historic Eroica bike race and a beloved spot for wine and culture lovers.

Casa Vacanze Vertine

Info

Day

Gaiole in Chianti – La Madonna

Duration: 04:35 h

Distance: 14.8 km

Ascent: 550 m

Descent: 590 m

On this final day of hiking, you’ll leave Gaiole and make your way to the majestic Castello di Brolio, perched atop a hill and surrounded by rolling vineyards. Here, take a guided tour and enjoy a tasting of Chianti wines, immersing yourself in the rich history of the region.

From the castle, continue your scenic walk through the tranquil Tuscan landscape to La Madonna, where you’ll spend a relaxing evening in the heart of nature. This is the perfect ending to your Chianti journey—a chance to unwind, take in the peaceful surroundings, and enjoy the starry sky as you reflect on a week of discovery and unforgettable moments.

RICASOLI Brolio Agriroom

Info

Day

Departure

After one last breakfast surrounded by the beautiful Tuscan landscape, it’s time to say goodbye to the Chianti region. You’ll return home with memories of charming villages, rolling vineyards, and the rich flavors of Chianti wines—perhaps even with a bottle or two to savor later and relive the journey.

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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?

How to Book

Booking
Availability
Cancellation policy

Best of Chianti

Itinerary

Arrival in Greve

Albergo Casa Al Sole

Greve - Radda in Chianti

Palazzo Leopoldo Dimora Storica & Spa

Radda – Gaiole in Chianti

Casa Vacanze Vertine

Gaiole in Chianti – La Madonna

RICASOLI Brolio Agriroom

Departure

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?

How to Book

Booking

Availability

Cancellation policy

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