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This Tuscan walking tour takes you through the enchanting Chianti Region. This is a great way to explore Tuscany on foot, while tasting the world-renowned offerings of the region, including signature Chianti wine and Florentine cuisine.
This walking tour of Tuscany’s Chianti region begins in Florence, where Renaissance atmosphere and magnificent architecture greet you. Then, you’ll travel to the village of Settignano to begin your walk. Here, olive groves, cypress trees, and all of Florence sprawl below you. Walking through Greve in Chianti gives you the chance to shop at a local market before tasting over 50 of the region’s best wines.
The next stop on this Chianti walking tour continues with a loop walk of Pananzo, where you can truly appreciate the wonderful Chianti landscape. You then walk through Badaccia to a century-old chestnut forest, and then through quaint hamlets. Stop for a glass wherever you please before continuing to the old town of Radda to explore the church of Santa Maria Novella.
The last leg of the Chianti walking tour starts in Siena, a town with a beautiful shell-shaped main square and countless imposing medieval towers and palaces. Relax with one last glass of fine wine before the end of your tour. This walking tour of Tuscany’s Chianti region is a must-do!
Walking in Chianti Tour
This Tuscan walking tour takes you through the enchanting Chianti Region. This is a great way to explore Tuscany on foot, while tasting the world-renowned offerings of the region, including signature Chianti wine and Florentine cuisine.
This walking tour of Tuscany’s Chianti region begins in Florence, where Renaissance atmosphere and magnificent architecture greet you. Then, you’ll travel to the village of Settignano to begin your walk. Here, olive groves, cypress trees, and all of Florence sprawl below you. Walking through Greve in Chianti gives you the chance to shop at a local market before tasting over 50 of the region’s best wines.
The next stop on this Chianti walking tour continues with a loop walk of Pananzo, where you can truly appreciate the wonderful Chianti landscape. You then walk through Badaccia to a century-old chestnut forest, and then through quaint hamlets. Stop for a glass wherever you please before continuing to the old town of Radda to explore the church of Santa Maria Novella.
The last leg of the Chianti walking tour starts in Siena, a town with a beautiful shell-shaped main square and countless imposing medieval towers and palaces. Relax with one last glass of fine wine before the end of your tour. This walking tour of Tuscany’s Chianti region is a must-do!
Explore the history, food and wine of incredible Tuscan towns like Florence, Radda and Siena.
Walk through the wine hills of Chianti and visit the region’s stellar wineries.
Taste local specialties like salami, Florentine steak, Cantucci, and plenty of wine.
Explore never-ending impeccable scenery and meet friendly locals on your travels.
Trip map
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Why book with 10 Adventures?
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Experience the trip of a lifetime organized by a team of travel specialists who combine knowledge and passion for adventure travel.
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With over 600 tours across 30+ countries, we specialize in self-guided tours.
Combine the freedom of travelling on your own with the confidence that all of your logistics are taken care of.
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Get everything you need for your next vacation with one easy booking.
We take care of accommodations, luggage transfers, gear rentals, and more - so you can focus on making memories.
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Explore our flexible booking, payment, and cancellation options, as well as our Lifetime Deposits program.
Solo Traveller
Single Room (2+)
Double/Twin Room
Triple Room
| Dates | Solo Traveller | Single Room (2+) | Double/Twin Room | Triple Room |
|---|---|---|---|---|
| Apr 1, 2025 to Apr 11, 2025 | $2,075USD | $1,795USD | $1,250USD | $1,075USD |
| Apr 12, 2025 to May 25, 2025 | $2,075USD | $1,795USD | $1,275USD | $1,075USD |
| May 26, 2025 to Oct 4, 2025 | $2,150USD | $1,875USD | $1,275USD | $1,075USD |
| Oct 5, 2025 to Oct 18, 2025 | $2,075USD | $1,795USD | $1,250USD | $1,075USD |
| Oct 19, 2025 to Oct 31, 2025 | $2,075USD | $1,775USD | $1,225USD | $1,050USD |
| Optional Extras | ||||
| Printed trip documents:$50USD | ||||
Meals
7 breakfasts are included.
Accommodations
Accommodation for 7 nights is included.
Transportation during the Tour
Transportation for you and your luggage is included as per the itinerary.
Also Included
- Digital information kit and app
- Maps and detailed information packs
- 24/7 telephone guidance and support
Not included
- Travel insurance
- Transfers not mentioned as ‘included’
- Lunches and dinners or drinks and snacks
- Tourist taxes (€1.5 – 4.8 EUR per person daily)
- Personal equipment
Optional Extras
- Any additional nights before or after tour
- Airport transfers
- Paperback trip documents
Accommodation for Walking in Chianti Tour
This tour is based in 2- 4-star hotels, but there is an option to book in upgraded hotels if you’d like a more luxurious stay.
The hotels offer pleasant rooms with excellent locations. Rooms are double occupancy, and single travelers will pay a supplement. In some cases, accommodation listed below may need to be substituted for other, comparable accommodations.
Single Rooms and Solo Travelers
Solo travellers must pay a supplement that varies based on the season (please inquire to find out more). However, it’s definitely possible to match single travellers up.
How hard is the Walking in Chianti Tour?
We rate this tour as a 3 / 5. While the distances aren’t that long, the Chianti region is very hilly, and there is moderate elevation gain most days.
Do I need a Visa to travel to Italy?
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
Are meals included on the Walking in Chianti Tour?
7 breakfasts are included.
Do I need insurance?
Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.
How do I get to Florence to start this tour?
The best airport to arrive at is Florence (FLR). From FLR, take the direct local bus to downtown.
Is the Walking in Chianti Tour guided?
No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.
Where does the Walking in Chianti Tour end?
The tour ends in Siena, where you can travel from the SITA-TRA.IN bus station to Florence. Check the bus schedule here.
I’ve never been on a self-guided trip! How does it work?
Self-guided travelling is not difficult! For many, it is a preferred type of travel as you are in charge of your own time and pace. You are provided all the information on which direction you need to go daily. You don’t need to carry lots of things with you and can only carry your daypack, as your luggage will be picked up from your hotel daily in the morning and delivered to your destination hotel.
Can I rent any equipment?
No, please come prepared with any walking/hiking equipment desired.
Do I need special vaccines to travel to Italy?
Check with your family doctor.
Are there any travel restrictions for Italy?
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.