Best of Chianti

Duration: 5 days
Trails: T1 trails
Distance: 15 - 20 km / 9 - 12 mi per day
Ascent per day: 500 - 1000 m / 1640 - 3281 ft ascent per day

> 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

See entire itinerary

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