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Chianti Wine Trails: Florence to Siena 73

Chianti Wine Trails: Florence to Siena

Tour details

from $805
Average rating:   0,  0 reviews
Activity type
Self Guided Walking
8 days & 7 nights
Easy to Moderate
April - October


Day 1: Florence
Day 2: Florence
Day 3: Greve in Chianti
Day 4: Greve in Chianti
Day 5: Radda in Chianti
Day 6: Radda in Chianti
Day 7: Siena
Day 8: Departure

Overview for Chianti Wine Trails: Florence to Siena

Follow the wine trails of Tuscany on foot through the wine region of Chianti, nestled between the beautiful cities of Florence and Siena. The Chianti region offers natural beauty and culinary treasures including the world-famous Chianti wines. The rolling Chianti hills are carpeted with olive groves, vineyards and fields that have come from a Renaissance painting. This region has been producing velvety red wines since the 13th century and there will be many opportunities during your walks to visit local vineyards and to enjoy some wine tasting.

First overnight is in Florence and last one is in Siena, but we strongly recommend that you spend some extra nights in both cities: Florence, famed for Michelangelo’s statue of David, the Uffizi art gallery and the fascinating Ponte Vecchio over the River Arno; and Siena, the jewel among the Renaissance cities of Tuscany with the imposing Piazza del Campo.


  • Florence, the cradle of the Renaissance and Medieval Siena
  • Fiesole and the Ancient Roman amphitheatre
  • The wine hills of Greve in Chianti and Radda in Chianti
  • Great wineries to visit and wines to taste
  • Wonderful landscapes, medieval villages and hamlets
  • Friendly people, great salami, Florentine steak, Cantucci with vinsanto…

Itinerary for Chianti Wine Trails: Florence to Siena

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Day 1: Arrive in Florence

Arrival in Florence on your own. Depending on the time of your arrival you have the rest of the day for exploring the numerous sites of the capital city of the Renaissance. We strongly recommend that you book an extra night in Florence before the holiday in order to have time to explore this beautiful city.

Day 2: Settignano to Fiesole

After breakfast, you take a 25-minute local city bus ride to the village of Settignano where the walk begins. During the walk, you will enjoy magnificent views of cypress trees, olive groves, Renaissance villas and the whole city of Florence at your feet. You will also stroll through the charming town of Fiesole and tour its Etruscan ruins, Roman amphitheatre and a Franciscan monastery.

  • Accommodation: Hotel Malaspina
  • Walking for the day (option 1): approx. 3 hours, 8 km, ­↑­­­­347 m ↓567 m
  • Walking for the day (option 2): approx. 6 hours, 16 km, ­↑­­­­567 m ↓566 m

Day 3: Greve in Chianti Circular Walks

After breakfast, а transfer takes you to Greve in Chianti, a rustic market village and the capital of the Chianti wine-producing region. Check in to the hotel and head over to Le Cantine di Greve where you can taste over 50 different Chianti wines. Take advantage of the daylight to walk around the gorgeous scenery by choosing between two routes.

Walk A: Greve in Chianti loop via Uzzano
In the afternoon, make a round walk north of the attractive main square of Greve in Chianti, through a picture-perfect landscape. From the main square, a round walk starts and takes you through the Chianti Classico area passing by the Villa Calcinaia and numerous vineyards with “aziende agricole” (farms) where the Chianti wine is produced.

  • Walking for the day: approx. 2.5 hours, 11.4 km, ­↑­­­­425 m ↓445 m

Walk B: Greve in Chianti loop via Montefioralle
Explore the wonderful surroundings through the forest, among dense wild vegetation, villas, vineyards and olive groves. You will be passing by abandoned old farms, ruins and beautiful villas before reaching the scenic hamlet of Montefioralle.

  • Walking for the day: approx. 3.5 hours, 10 km, ­↑­­­­360 m ↓355 m

Day 4: Panzano Circular Walk

Walk through the hills surrounding the village of Panzano, enjoying the classic Chianti landscape of forests and vineyards and discovering ancient Roman farmsteads in the region.

  • Accommodation: Albergo Casa al Sole
  • Walking for the day: approx. 4 hours, 11.7 km, ­↑­­­­385 m ↓385 m

Day 5: Badiaccia a Montemuro to Radda in Chianti

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele from where you descend through a forested valley of century-old chestnut trees and continue towards the stunning medieval hamlet of Volpaia, situated amongst vineyards and castles. Stop in for a glass of red at a fine Enoteca, wine shop, and then continue on to Radda in Chianti.

Day 6: Radda in Chianti Circular Walk

Today you go for a scenic walk around  Radda in Chianti. Stop for lunch in the lovely hamlet of Vertine and in the afternoon treat yourself to a glass of Chianti wine at Colle Bereto, a celebrated local vineyard that you will reach along the way back to Radda.

Day 7: Siena

After breakfast, a transfer takes you to the marvellous city of Siena, famous for its biannual Palio horse race, held in the city’s famous square: the Piazza del Campo. You have the whole day for exploring the architectural treasures of the city, and if it is not enough, you can book an extra night.

Day 8: Departure

Departure on your own or extension upon request.

Hotels for Chianti Wine Trails: Florence to Siena

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Accommodation is in selected B&Bs and 2&3-star hotels, all with en-suite facilities and a good Italian breakfast included each morning. All places have been carefully hand-picked by us and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Sample hotels: Hotel Malaspina, Albergo Casa al Sole, Affittacamere Giovannino, Cannon d’Oro

Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.


The trip is on a bed and breakfast basis as throughout the trip there are plenty of opportunities for you to taste both the outstanding local cuisine and a wide range of fine  regional wines. Dinner is available either from the restaurant in your accommodation or the restaurants in the town where you stay for overnight.

Travel for Chianti Wine Trails: Florence to Siena

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By Plane

Our recommended arrival/departure airports for this holiday are the ones in Florence, Pisa or Bologna, which are all served to by the major and low-cost international carriers.

By Bus

All three airports are connected to the major cities in the area by local transport, which is affordable and offers a frequent service. From Florence airport, you can take a direct local bus to downtown. From Pisa airport, you can take either a direct train or bus to Florence. From Bologna airport take the bus to Bologna central station, then the train to Florence.

By Car

If you come with your own car, please note that the hotels used in Florence and Siena do not have a private parking lot. There are several guarded parking areas which cost approximately 20 EUR per day.

Private Transfers

Airport transfers by public transport are recommended for this trip, as they are much cheaper and faster compared to car transfers.

Baggage Transfers

Hotel to hotel luggage transfer is included on all walking days.

Travel Insurance

A comprehensive and reputable travel insurance policy is essential to your enjoyment and peace of mind while on an active holiday. It is highly recommended when booking with us that all group members have valid travel insurance which includes cover for all activities included in your trip. We have teamed up with World Nomads Logo to offer you adequate cover at a great value from a reputable insurer, and it takes only a few minutes to buy online.

Buy travel insurance online

Country Info

Language: Italian. In big cities and resorts, many people speak English, but in remote areas, this might not be the case. However, most of the hotel personnel where we stay speak English and are ready to help you. You can always call our 24/7 helpline if there are any problems.

Electric supply and plugs: 220V, 50hZ, two-pin round plugs.

Currency: We strongly advise taking sufficient cash for your daily requirements. Banks and ATMs are available, and credit/debit card payments are widely accepted in towns and cities and big petrol station chains but might be limited at some of the villages we visit.

Up-to-date travel advice on Italy is available here.

Detailed travel information and hints will be provided in your holiday information pack.

Trip Info for Chianti Wine Trails: Florence to Siena

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Difficulty Grade: Easy to Moderate

This is a self-guided walk with average daily walking stages taking between 3-5 hours and you are usually able to choose the route for the day according to your abilities. The paths are clearly visible and well-marked, no technical skills are required. A basic level of fitness is required for enjoying the walks to the maximum (read more about difficulty grades).

Route Navigation

We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime. More detailed info on route navigation will be included in your holiday information pack.

When to Go

This trip can depart every day between early April and end of October.

What to Bring

We recommend that you travel as light as possible – airlines might charge you an extra fee, and during ground transfers, the place might be limited. Ideally, you should bring one piece of luggage weighing no more than 25 kg (to be checked in) and a daily pack (15 – 20 l rucksack) for your everyday essentials (snacks, drinking water, camera, etc.). Below is a non-exclusive list of what you should bring to this trip. More detailed info will be included in your holiday information pack. If you need further advice, please contact a reputable outdoor retailer or us.

  • Good hiking boots
  • Hiking socks
  • Several t-shirts (cotton or preferably breathable/fast drying)
  • Packable waterproof and windproof jacket with hood
  • Synthetic mid layer or warm fleece
  • Trainers and/or sandals – to relax and wear inside the accommodation
  • Sunglasses, sunscreen and lip salve
  • Hat/Baseball cap
  • Personal First Aid kit (wet wipes, flu remedies, stomach remedies)

Included for Chianti Wine Trails: Florence to Siena

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  • 7 nights in selected B&Bs and 2&3-star hotels
  • 7 breakfasts
  • Luggage transfers on all walking days
  • Transfer from Florence to Greve in Chianti on Day 3
  • Transfer from Greve in Chianti to Badiaccia luggage to Radda in Chianti on Day 5
  • Transfer from Radda in Chianti to Siena on Day 7
  • Detailed route notes in electronic format (you can print them in advance if you wish)
  • 24/7 telephone support

Single Room & Solo Traveller Supplements

  • Where individual members of a group require a single room, a single room supplement is applicable.
  • This holiday is available for solo travellers. As costs are not shared, a supplement is payable on the standard trip cost

Please click the CHECK AVAILABILITY button above to see the price of the holiday and the different options, extras and supplements for your desired dates.

Options and Extras

  • Private airport transfers can be arranged upon request
  • Additional nights before, during or after the walk

Other Trip-Related Costs

  • Airport train and bus fares
  • Entrance fees for attractions and museums


  • Airfare and connecting transfers
  • Lunches & dinners
  • Drinks and snacks
  • Personal equipment
  • City tourist taxes
  • Any items not explicitly mentioned as ‘included’ in the programme

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