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Highlights
Discover the delightful food and drink of Chianti on this self-guided walking tour
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.
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!
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!
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Walking in Chianti Tour Itinerary
Day 1 Arrival in Florence
Arriving in Florence marks the start of your walking tour of Chianti. Breathe in the city air and take some time to explore Florence’s stellar collection of Renaissance buildings and squares. Walk along the flowing Arno River. Stroll to the Piazza della Signoria before finding one of the many excellent restaurants for dinner.
Overnight Location: Hotel in Florence
Distance: None
Meals: None
Day 2 Walk to Fiesole
A quick morning bus ride takes you to Settignano, where you will begin today’s walk. You’ll pass lush cypress forests, olive groves, and have a birds-eye view of Florence. The colorful town of Fiesole is a great chance to see Etruscan ruins, a preserved Roman Amphitheatre, and a Franciscan monastery before the day ends.
Overnight Location: Hotel in Florence
Distance: 3/6 hours, 8/16km, 224/556m elevation gain
Meals: Breakfast
Day 3 Choice of walks in Greve in Chianti
This morning, take a quick transfer to Greve in Chianti, where rustic markets and excellent wine await. Once you’re checked in to your hotel, stop by Le Cantien di Greve for a tasting of over 50 of the region’s fine wines. Then, you have the choice of two routes for today’s walk. The first starts in Greve’s main square, and then leads you through the Chianti Classico region. On this walk, you get wonderful vineyard views and glimpses at the “azende agricole” where the wine is produced. The second option heads into the nearby forest, where you’ll pass through lush wild vegetation, olive groves, and vineyards. Abandoned farms beckon you for a look and beautiful villas dot the trail. You’ll take a moment to appreciate the panoramic view from Montefioralle before heading back to Greve.
Overnight Location: Hotel in Greve
Distance: 2.5 hours, 11.4 km, 425m elevation gain or 3.5 hours, 10 km, 447m elevation gain
Meals: Breakfast
Day 4 Pananzo loop walk
The next leg of your walking tour of Chianti is a loop walk based out of Panzano. The village is surrounded by undulating hills, and the trademark Chianti vineyards and forests surround you.
Overnight Location: Hotel in Greve
Distance: 4 hours, 11.7 km, 384m elevation gain
Meals: Breakfast
Day 5 Radda in Chianti
A morning transfer takes you up to the topmost Chianti hill, Monte San Michele. Your walk descends through a tree-clad valley of century-old chestnut trees before pausing in Volpaia. Grab lunch and a glass of wine at one of the enotecas before continuing on to Radda in Chianti.
Overnight Location: Hotel in Radda
Distance: 4 hours, 13 km, 506m elevation gain
Meals: Breakfast
Day 6 Radda in Chianti loop
Today’s walk is pleasant and relaxing. The warm Tuscan sun warms your shoulders while you tour the old centre of Radda. Then, follow the alleyways to the church of Santa Maria Novella. The roads winds up through vineyards, where you’re welcome to stop for a glass at the excellent local wineries.
Overnight Location: Hotel in Radda
Distance: 5 hours, 15.8 km, 586m elevation gain
Meals: Breakfast
Day 7 Siena
After breakfast, transfer to Siena. Siena is a stunning city packed to the brim with Renaissance history. Snap a photo in the shell-shaped square where the biannual Palio horse race occurs, or stop by the architectural hotspot of the Duomo. There are medieval palaces and towers everywhere, and they make a perfect backdrop for the day’s exploration. You’re welcome to explore Siena as you please today with no set route, so spend time where you enjoy it best!
Overnight Location: Hotel in Siena
Distance: None
Meals: Breakfast
Day 8 Departure from Siena
A final breakfast caps off the Walking in Chianti Tour. You’re welcome to book more nights in Siena if you’re not quite done exploring!
Overnight Location: None
Distance: None
Meals: Breakfast
The departure is available any day of the week. Prices below are per person:
Departure on April 16th – October 8th, 2023:
- Solo traveller: EUR1606
- Single room (group of 2+): EUR1398
- Sharing a double/twin room: EUR949
- Sharing a triple room: EUR790
Departure on October 8th – 31st, 2023:
- Solo traveller: EUR1531
- Single room (group of 2+): EUR1323
- Sharing a double/twin room: EUR904
- Sharing a triple room: EUR790
Departure on April 1st – 18th, 2024:
- Solo traveller: EUR1444
- Single room (group of 2+): EUR1669
- Sharing a double/twin room: EUR998
- Sharing a triple room: EUR863
Departure on April 19th – May 25th, 2024:
- Solo traveller: EUR1474
- Single room (group of 2+): EUR1699
- Sharing a double/twin room: EUR1028
- Sharing a triple room: EUR883
Departure on May 26th – October 12th, 2024:
- Solo traveller: EUR1534
- Single room (group of 2+): EUR1759
- Sharing a double/twin room: EUR1028
- Sharing a triple room: EUR883
Departure on October 13th – 31st, 2024:
- Solo traveller: EUR1444
- Single room (group of 2+): EUR1669
- Sharing a double/twin room: EUR983
- Sharing a triple room: EUR833
Accommodation on the 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.
What’s included in the Walking in Chianti Tour?
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
- How hard is the Walking in Chianti Tour?
- Do I need a Visa to travel to Italy?
- Are meals included on the Walking in Chianti Tour?
- Do I need insurance?
- How do I get to Florence to start this tour?
- Is the Walking in Chianti Tour guided?
- Where does the Walking in Chianti Tour end?
- I’ve never been on a self-guided trip! How does it work?
- Can I rent any equipment?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
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.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
7 breakfasts are included.
Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.
The best airport to arrive at is Florence (FLR). From FLR, take the direct local bus to downtown.
No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.
The tour ends in Siena, where you can travel from the SITA-TRA.IN bus station to Florence. Check the bus schedule here.
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.
No, please come prepared with any walking/hiking equipment desired.
Check with your family doctor.
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.
Customer Ratings
S-Cape Travel is a boutique tour operator focused on sharing the best walking, cycling, cultural and food & wine tours in Europe. Book one of their self-guided tours to live La Dolce Vita for a week or two, as you walk or cycle around Europe, enjoying incredible views and amazing food and wine.
