Tour Name: The Chianti from Florence to Siena
Description | Map | Days | Tripnotes | Period | Included | Not included | Notes | Equipment
Type: 7 days Self guided Walking tour
Skill level:
medium
Price per person: 540 €
No. min. of participants: 2
Gallery [top]
Day 1| Firenze

Highlights [top]
- Florence and the hills of Fiesole
- Siena
- San Gemignano : an original approach from Colle val d’Elsa
- The discovery of the Chianti region and of the Val d’Elsa.
- The villages of the Chianti region : Castellina and Radda in Chianti
- The castles of Brolio, Castagnoli and Meleto
Description [top]
From Piazza della Signoria to Piazza del Campo, a trek to join two of the most important Tuscan cities from the historical and artistic point of view.
Florence, the city of Leonardo, Giotto, Dante and Brunelleschi, and Siena, native land of the "Palio". These two jewels have in common the fact that they belong to one of the most famous areas of the Tuscany: "the wine road", that you will cross leaving Castellina in Chianti and walking along paths and roads surrounded by vineyards and olive groves.
The typical Chianti landscape is a hilly, varied and colourful landscape: here is where the famous wine - produced since Etruscan age - is born. However, this area doesn’t consist exclusively in vineyards and olive groves. Depending on the season the nature offers fabulous and colourful sceneries: from the red of the poppies to the violet of the irises, from the yellow of the brooms to the green of the firs and cypresses.
Moreover, golden stone villages are scattered in the landscape: Gaiole, San Donato, Pieve di San Giusto, the castle of Vertine and Galena, and several other castles as the Castle of Meleto, the fortified village of Castagnoli and the famous Castle of Brolio, property of the Ricasoli baron.
In this Castle, rich in suggestions of ancient times, you will certainly have the possibility of tasting some good wine. The last part of the trek takes you to Colle Val d' Elsa, a lovely medieval village and then, along the Francigena way, up to Saint Gimignano.
Days detail [top]
Day 1 | Firenze, Tuscany, Italy
Individual arrival in Florence, free time to visit the magnificent city of art, a real open-air museum. The city of Leonardo da Vinci, Machiavelli, Giotto, Dante and Brunelleschi, it pervades your soul with wonder at your first visit, but it is indeed capable of offering precious surprises and new treasures to all the people who like to come back again. You are free for dinner. Spend the night in hotel in the city centre.
Day 2 | Fiesole, Tuscany, Italy
Florence – Fiesole 3h walking
After breakfast hike to Fiesole: walk through olive groves and cypress lined roads, coming across the magnificent villas dominating the Val d’Arno. The beauty of the landscape is impressive, once you have reached the hill top you can enjoy an astonishing view over Florence. In the main square of Fiesole you can admire the Dome and the Magisterial Palace, dating back to the fourteenth century, the town also hosts valuable archaeological sites. Return to Florence. You are free for dinner. Spend the night in hotel in the city centre.
Day 3 | Radda in Chianti, Tuscany, Italy
Castellina in Chianti – Radda in Chianti 4h30 walking
After breakfast transfer, by public transport, to get to Poggibonsi. From there, private transfer to get to Castellina in Chianti. Today’s route moves through one of the most celebrated stretch of Tuscany land: “the road of Wines”. Start from Castellina in Chianti and rumble on paths and country roads, crossing vineyards and olive groves, to reach the medieval village of Radda in Chianti. The Chianti Classico Wine District lays in between Florence and Siena and its landscapes reveal the charming and variegated nature of this unique countryside. This is the land where the renowned Chianti Classico wine is produced and it is the same land where wine has always been produced.
Day 4 | Gaiole in Chianti, Tuscany, Italy
Radda in Chianti – Gaiole in Chianti 5h30 walking
After breakfast leave the Hotel, in the heart of Chianti, to reach Gaiole in Chianti.
The great appeal of this surroundings is not simply bound to vineyards and olive groves, in fact, here nature can offer enchanting sceneries of changing colours, depending on the season: the red of poppy fields, the violet dots of irises, the strong yellow of broom bushes, the intense green of cypresses and fir-trees. And, like a stoke of brush on the landscape, the stone-made villages add a bright golden colour to the picture. Look at Gaiole, San Donato, Pieve di San Giusto, Vertine Castle (which dates back to the year 1020), and the eleventh century tiny village of Galena.
Day 5 | Castello di Brolio, Arezzo, Tuscany, Italy
Gaiole in Chianti – Castello di Brolio 4h walking
Castles’ day. Departure from the hotel. First stop of the day is at Meleto Castle, a fortified edifice built in the fifteenth century and then converted during the nineteenth century into a magnificent villa, with the typical style of Tuscan countryside. Carry on the castles’ tour passing through the fortified village of Castagnoli and getting to the famous Brolio Castle, property of the Ricasoli Baron, a suggestive site filled with the charm of past times. You can enter past the castle walls and walk the ancient rounds. If you like, have a look at the Ricasoli wine vaults and take the chance for a wine tasting. Transfer to Siena on private minibus (15 km). You are free for dinner.
Day 6 | San Gimignano, Tuscany, Italy
Colle Val d’Elsa – San Gimignano 4h30 walking
Transfer by public bus to Colle val d’Elsa, visit to the town and then hike to Quartaia, a small rural village of mediaeval origins. Resume the journey through the hills to get to Coneo Abbey, founded around the year 1000, by the Benedictines. Walking on the historic Via Francigena you arrive at Molino d'Aiano. At this point the mild and peaceful panorama is already gently dominated by the unmistakable shape of San Gimignano hill. Declared by the UNESCO World Human Heritage, the city of San Gimignano holds, still intact, its mediaeval urban architecture. The spectacle of the view you can get from the top of one of the several town towers is invaluable!
Day 7 | Siena, Tuscany, Italy
Siena
After breakfast you are free to visit Siena, the famous town of the Palio. Situated on a peculiar territory, Siena is characterised by a quaint scenery, the city unrolls in a continuous up and down of streets, where you can discover the most notorious monuments, like the Buonsignori Palace, with its National Picture Gallery, the white and dark green marble decorated Dome, of which the construction started back in twelfth century, the Piccolomini Library, the Baptistery and the Museum of Metropolitan Opera, or you can simply enjoy a stroll around Piazza del Campo and along the narrow streets, stopping for a taste of Panforte and Ricciarelli in some of the several typical confectioner’s shops. Departure in the early afternoon.
Trip notes [top]
Period [top]
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
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Included [top]
- Accommodation A - in hotel***/**** or B in hotel ***, in double room with private facilities
- Bed and breakfast on day 1-2-5-6, half board on day 3-4
- Luggage transport
- Transfer by private minibus Poggibonsi-Castellina and Brolio-Siena
- Detailed description of the itinerary
Not included [top]
- Journey to Firenze and from Siena
- Lunches, dinners on day 1-2-5-6
- Drinks
- Transfer with public buses
- Insurance
- Entrance fees
- Everything not specified
Notes [top]
- Terrain characteristics: Paths and easy country roads, hilly area. It is advisable to have done a little trekking practice or a little training. Trekking height: between 100 and 550 mt, average duration of the stages between 4 and 5.30 hours, positive difference in height from 150 to 400 mt per day.
- Departures: on Sundays from 16 of March to 26 October
- Private vehicle from Poggibonsi to Castellina, from hotel in Radda to Gaiole and from Brolio Castle to Siena.
- Public bus from Florence to Poggibonsi, from Siena to Colle Val d’Elsa and from San Gimignano to Siena.
Equipment [top]
- [Da inserire]
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