Overview
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 world-famous Chianti wines. The rolling Chianti hills are carpeted with olive groves, vineyards, and fields 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 enjoy some wine tasting.
First overnight is in Florence and the 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
Day 1: Arrive in Florence
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.
- Accommodation: Hotel Camilla in Florence or similar (optional upgrade: Hotel Park Palace)
Day 2: Settignano – Fiesole | 8-16km
After breakfast, you take a 25min 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.
- Walking for the day (option 1): approx. 3h, 8km, ↑347m ↓224m
- Walking for the day (option 2): approx. 6h, 16km, ↑567m ↓566m
- Accommodation: Hotel Camilla in Florence or similar (optional upgrade: Hotel Park Palace or similar)
Day 3: Greve in Chianti Circular Walks | 9-10km
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.
- Accommodation: Albergo Casa al Sole in Greve in Chianti (optional upgrade: Albergo del Chianti)
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. 3h, 9km, ↑225m ↓225m
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. 3.5h, 10km, ↑360m ↓355m
Day 4: Panzano Circular Walk | 11.7km
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.
- Walking for the day: approx. 4h, 11.7km, ↑385m ↓385m
- Accommodation: Albergo Casa al Sole in Greve in Chianti (optional upgrade: Albergo del Chianti)
Day 5: Badiaccia a Montemuro – Radda in Chianti | 14km
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 to Radda in Chianti.
- Walking for the day: approx. 5h, 14km, ↑506m ↓668m
- Accommodation: La Bottega di Giovannino in Radda in Chianti (optional upgrade: Palazzo San Niccolò)
Day 6: Radda in Chianti Circular Walk | 15.8km
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.
- Walking for the day: approx. 5h, 15.8km, ↑586m ↓586m
- Accommodation: La Bottega di Giovannino in Radda in Chianti (optional upgrade: Palazzo San Niccolò)
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 exploring the architectural treasures of the city, and if it is not enough, you can book an extra night.
- Accommodation: Cannon d’Oro in Siena or similar (optional upgrade: Hotel Chiusarelli or similar)
Day 8: Departure
Departure on your own or extension upon request.
What to expect
Accommodation
Accommodation is in selected B&Bs, and 2 or 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. Hotel upgrade is possible on request.
Click to view default hotels
- Hotel Camille (Florence)
- Albergo Casa al Sole (Greve in Chianti)
- La Bottega di Giovannino (Radda in Chianti)
- Albergo Cannon d’Oro (Siena)
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.
Click to view upgraded hotels
- Hotel Park Palace (Florence)
- Albergo del Chianti (Greve in Chianti)
- Palazzo San Niccolò (Radda in Chianti)
- Hotel Chiusarelli (Siena)
Hotels are subject to availability. In the event of a particular hotel being fully booked for your chosen 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.
Meals
The trip includes breakfast; there are plenty of opportunities for you to taste both the outstanding local cuisine and a wide range of fine regional wines. Please note that breakfast in Radda in Chianti is served at a nearby bar. Dinner is available either from the restaurant in your accommodation or in the town where you stay overnight.
Difficulty and terrain
This is a self-guided walk with average daily walking stages taking between 3-5h, and you are usually able to choose the route for the day according to your abilities. A basic fitness level is required for enjoying the walks to the maximum (read more about difficulty grades). The walks are along small gravel roads (strade bianche), footpaths and mule tracks on hilly terrain. You will cross several small hamlets and some larger villages. 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
You can start your holiday every day between the beginning of April and the end of October. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August (If you’d like to catch the famous Palio di Siena, you will have to travel in July or August, however). In September – October, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.
Getting there
Click to view travel options
By plane
Our recommended arrival airports for this holiday are Florence, Pisa and Bologna. Other Italian airports are also well connected to the area.
By train or bus
- If you are able to travel to Italy without flying, this holiday is reachable by rail with train stations in both Florence and Siena. For more details, see Trenitalia.
- All three airports are connected to the major cities in the area by local transport, which is affordable and offers 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. Train schedules can be checked on the Trenitalia website, or you can use the Omio planner above.
Inclusions
Included
- 7 nights in selected B&Bs and 2 and 3-star hotels
- 7 breakfasts
- Luggage transfers on all walking days (one piece per person, up to 20kg)
- Transfer from Florence to Greve in Chianti on Day 3
- Transfer from Greve in Chianti to Badiaccia on Day 5
- Transfer from Radda in Chianti to Siena on Day 7
- Detailed digital holiday information pack including GPS-checked and regularly updated route descriptions, road notes and maps. Please note that the info pack is emailed to you prior to departure, and no printed documents are mailed or provided locally
- 24/7 telephone support by our local office/representative
Excluded
- Airfare and connecting land transfers
- Lunches and dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Local tourist tax and entry fees (payable locally)
- Personal expenses
- Any items not specifically mentioned as ‘Included’ in the programme
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- This holiday is available for solo travellers. However, a supplement will be charged as the cost of rooms and also luggage or private transfers (when applicable) is not shared. Please note that solo travellers are always accommodated in their own room. For logistical reasons, we don’t offer an option for solo travellers to share rooms with other solo travellers.
- Extra nights
- Upgraded hotels with a supplement
- The tour can be arranged as a 5-day/4-night programme
- Printed tour materials at the first accommodation
