Discover the Tuscan countryside and the magic that the Chianti Classico wine region has to offer: vineyards, medieval villages, cypress trees, quiet oak forests, the lively atmosphere of the piazzas, rustic food and of course the fine Chianti Classico wines!
Our hiking holidays in Tuscany are ideal for weekends or full weeks. Whichever you choose, we start in Florence, visit the classic villages of Greve in Chianti and Radda in Chianti, and finish in Siena.
We have included special private transfers to and from the start and end of almost all the walks, so you can enjoy the scenery at your leisure, while visiting all the highlights of the area.
Hike in the incredibly beautiful and picturesque region of Tuscany
Highlights
- Explore the cradle of the Renaissance in romantic Florence
- Hike along vineyards on the beautiful hills of Chianti
- Visit vineyards and taste great wines
- Stroll across the Piazza del Campo in Siena
Quick facts
| Travel duration: | 8 days/ 7 nights, 5 days/ 4 nights, 4 days/ 3 nights |
|---|---|
| Travel period: | Optional departure day during the period 1/4 - 31/10 |
| Grade: | Easy. Average 3-4 h/7-12 km/ 200-400 m per day. Day by day trip grading, see "program" on each trip. 2 |
| Accommodations: | |
| Trip type: | Self guided walking holidays |
| Price example: | From €580 |
| Meals: | Breakfast |
Prices per person in EUR
This trip is available from April 1 – October 31, with any arrival date.
4 days/ 3 nights From €650 Book your trip
| Period | TRP - Triple Room | Double Room - shared bed | Twin Room - separate beds | SGL - Single Room |
|---|---|---|---|---|
| 2025-09-01 2025-10-31 | €650 | €760 | €760 | €940 |
| 2026-04-01 2026-10-31 | €690 | €810 | €810 | €1,010 |
5 days/ 4 nights, hotel *** From €630 Book your trip
| Period | TRP - Triple Room | Double Room - shared bed | Twin Room - separate beds | SGL - Single Room |
|---|---|---|---|---|
| 2025-08-30 2025-10-31 | €640 | €750 | €750 | €900 |
| 2026-04-01 2026-06-30 | €630 | €760 | €760 | €900 |
| 2026-07-01 2026-08-29 | €630 | €750 | €750 | €900 |
| 2026-08-30 2026-09-30 | €650 | €760 | €760 | €920 |
5 days/ 4 nights, hotel ***/**** From €580 Book your trip
| Period | TRP - Triple Room | Double Room - shared bed | Twin Room - separate beds | SGL - Single Room |
|---|---|---|---|---|
| 2025-09-01 2025-10-31 | €580 | €700 | €700 | €960 |
| 2026-04-01 2026-04-21 | €630 | €760 | €760 | €1,030 |
| 2026-04-22 2026-06-20 | €630 | €770 | €770 | €1,050 |
| 2026-06-21 2026-07-06 | €630 | €760 | €760 | €1,030 |
| 2026-07-07 2026-10-17 | €630 | €770 | €770 | €1,050 |
| 2026-10-18 2026-10-31 | €630 | €760 | €760 | €1,030 |
8 days/ 7 nights, hotel *** From €730 Book your trip
| Period | TRP - Triple Room | Double Room - shared bed | Twin Room - separate beds | SGL - Single Room |
|---|---|---|---|---|
| 2025-08-30 2025-10-31 | €750 | €870 | €870 | €1,260 |
| 2026-04-01 2026-04-28 | €730 | €870 | €870 | €1,240 |
| 2026-04-29 2026-06-30 | €760 | €890 | €890 | €1,270 |
| 2026-07-01 2026-08-29 | €730 | €860 | €860 | €1,230 |
| 2026-08-30 2026-09-30 | €760 | €890 | €890 | €1,270 |
| 2026-10-01 2026-10-31 | €730 | €870 | €870 | €1,160 |
8 days/ 7 nights, hotel ***/**** From €910 Book your trip
| Period | TRP - Triple Room | Double Room - shared bed | Twin Room - separate beds | SGL - Single Room |
|---|---|---|---|---|
| 2025-09-01 2025-10-31 | €910 | €1,060 | €1,060 | €1,520 |
| 2026-04-01 2026-04-18 | €980 | €1,140 | €1,140 | €1,650 |
| 2026-04-19 2026-06-20 | €1,000 | €1,170 | €1,170 | €1,680 |
| 2026-06-21 2026-07-03 | €980 | €1,140 | €1,140 | €1,650 |
| 2026-07-04 2026-10-17 | €1,000 | €1,170 | €1,170 | €1,680 |
| 2026-10-18 2026-10-31 | €980 | €1,140 | €1,140 | €1,650 |
Prices quoted are per person and include:
- Accommodation 3, 4 or 7 nights
- Breakfast included
- Luggage transport for hotel changes
- Transport to and from the start and end of the treks according to the programme
- English mobile app:
- Digital maps
- Destination information
- Practical information
- Detailed walk descriptions day by day
- 24 h emergency phone for urgent matters
Not included
- Flight to/from the destination
- Transfer to/from the airport
- Local ‘City Tax’ ‘Tassa di soggiorno’ in some villages. The tax is paid on the spot and the cost varies, about 2-5 Euro per night.
* Single room rates
- Single room rates apply when travelling in the company of others. If you are travelling on your own, in most cases there is an extra charge due to more expensive luggage transport. Please contact us for prices.
Optional extras
- Printed maps & walking directions: 30 Euro (picked up at check-in at the first hotel)
- Extra nights in Pisa, Florence or Siena can be pre-booked. Prices vary depending on season and accommodation standard. Please contact us for price information.
Itinerary
8 days/ 7 nights
Day 1 Arrival in Florence
If you arrive to Florence in good time, we recommend you to take a walk through the city, around its magnificent squares and across the famous Arno river.
Enjoy a good restaurant with local red wine in the evening.
Day 2 Hike from Sittignano to Fiesole – 8 km (16 km)
Today you will take either a local bus or taxi after breakfast up to the village of Settignano, where today’s hike begins. During the hike you will have magnificent views of Florence, and the hills with their olive groves and cypresses. Walk through the charming town of Fiesole and visit the Roman amphitheatre, the Etruscan ruins and the monastery. In the afternoon you will return to Florence, leaving you more time to explore this wonderful city and eat at a good restaurant in the evening.
8 km (16km), +350 m, -225m
Day 3 Hike around Greve in Chianti – 11,4 km (10 km)
After breakfast, a private transfer is included to the rustic village of Greve in Chianti, the ‘capital’ of the Chianti wine region. After checking into the hotel, we suggest a visit to Le Cantine di Greve, where you can taste over 50 different Chianti wines.
You can then choose between two different walks, one of which takes you through the Chianti Classico area and its vineyards via Uzzano. The slightly shorter walk takes you through vineyards, olive groves, etc. via the village of Montefioralle, which is located on a hill with lovely views.
11.4 km (10 km), +425 m (+358 m), -447 m (-355 m), 3.5 h (2.5 h)
Day 4 Hike around Greve in Chianti & Panzano – 12 km
After breakfast you take the local bus, about 10 min to Panzano in Chianti, where today’s hike begins.
Today you will hike over the hills in a varied landscape with both forest, many vineyards and beautiful medieval farms.
12 km, +385 m, -385 m, 4 h
Day 5 Hike from Badiaccia to Radda in Chianti – 14 km (9,5 km)
After breakfast, a short transfer is included to the highest mountain/hill in Chianti – Monte San Michele. From Badiaccia, you will descend through a chestnut forest and continue towards the stunning medieval village of Volpaia, set amongst vineyards and castles. Stop and sample red wines at a fine Enoteca and then continue to the cosy village of Radda in Chianti, where you will spend the night.
14 km (9,5 km), +539 m (+374 m), -707 m (-387 m), 5 h (3 h)
Day 6 Hike around Radda in Chianti – 17 km
A scenic and delightful day of hiking awaits you as you wander around the old village centre of Radda and then on to the stunning little village of Vertine, which is an ideal lunch stop.
In the afternoon you will hike back towards Radda in Chianti. Along the way we recommend you stop for a glass of Chianti at the famous Colle Bereto winery.
17 km km, +585 m, -585 m, 5 h
Day 7 Stroll through Siena - 0 km
After breakfast, a transfer from Radda in Chianti to Siena is included. Spend the rest of the day exploring Siena, famous for its biennial horse race, the Palio, in the beautiful shell-shaped Piazza del Campo. Don’t forget to visit to the Duomo, with its medieval palaces and cathedrals.
Stroll along the winding, narrow streets, relax with an espresso, and enjoy this amazing city!
Day 8 Departure day
The trip ends after breakfast.
From Siena, you can easily take a bus to Florence, which runs every 30 minutes, or book a private transfer (not included). You can also extend the trip with an extra day & night in Siena.
5 days/ 4 nights
Day 1 Arrival in Florence
If you arrive to Florence in good time, we recommend you to take a walk through the city, around its magnificent squares and across the famous Arno river.
Enjoy a good restaurant with local red wine in the evening.
Day 2 Hike around Greve in Chianti – 11,4 km (10 km)
After breakfast, a private transfer is included to the rustic village of Greve in Chianti, the ‘capital’ of the Chianti wine region. After checking into the hotel, we suggest a visit to Le Cantine di Greve, where you can taste over 50 different Chianti wines.
You can then choose between two different walks, one of which takes you through the Chianti Classico area and its vineyards via Uzzano. The slightly shorter walk takes you through vineyards, olive groves, etc. via the village of Montefioralle, which is located on a hill with lovely views.
11.4 km (10 km), +425 m (+358 m), -447 m (-355 m), 3.5 h (2.5 h)
Day 3 Hike from Badiaccia to Radda in Chianti – 14 km km (9,5 km)
After breakfast, a short transfer is included to the highest mountain/hill in Chianti – Monte San Michele. From Badiaccia, you will descend through a chestnut forest and continue towards the stunning medieval village of Volpaia, set amongst vineyards and castles. Stop and sample red wines at a fine Enoteca and then continue to the cosy village of Radda in Chianti, where you will spend the night.
14 km (9,5 km), +539 m (+374 m), -707 m (-387 m), 5 h (3 h)
Day 4 Stroll through Siena - 0 km
After breakfast, a transfer from Radda in Chianti to Siena is included. Spend the rest of the day exploring Siena, famous for its biennial horse race, the Palio, in the beautiful shell-shaped Piazza del Campo. Don’t forget to visit to the Duomo, with its medieval palaces and cathedrals.
Stroll along the winding, narrow streets, relax with an espresso, and enjoy this amazing city!
Day 5 Departure day
The trip ends after breakfast.
From Siena, you can easily take a bus to Florence, which runs every 30 minutes, or book a private transfer (not included). You can also extend the trip with an extra day & night in Siena.
4 days/ 3 nights
Day 1 Arrival in Florence
If you arrive to Florence in good time, we recommend you to take a walk through the city, around its magnificent squares and across the famous Arno river.
Enjoy a good restaurant with local red wine in the evening.
Day 2 Hike around Greve in Chianti – 11,4 km (10 km)
After breakfast, a private transfer is included to the rustic village of Greve in Chianti, the ‘capital’ of the Chianti wine region. After checking into the hotel, we suggest a visit to Le Cantine di Greve, where you can taste over 50 different Chianti wines.
You can then choose between two different walks, one of which takes you through the Chianti Classico area and its vineyards via Uzzano. The slightly shorter walk takes you through vineyards, olive groves, etc. via the village of Montefioralle, which is located on a hill with lovely views.
11.4 km (10 km), +425 m (+358 m), -447 m (-355 m), 3.5 h (2.5 h)
Day 3 Hike from Badiaccia - Radda in Chianti – Siena - 14 km (9,5 km)
After breakfast, a short transfer is included to the highest mountain/hill in Chianti – Monte San Michele. From Badiaccia, you will descend through a chestnut forest and continue towards the stunning medieval village of Volpaia, set amongst vineyards and castles. Stop and sample red wines at a fine Enoteca and then continue to the cosy village of Radda in Chianti.
After a visit to the cosy village, a transfer to Siena is included where you will spend the last evening and night.
14 km (9,5 km), +539 m (+374 m), -707 m (-387 m), 5 h (3 h)
Day 4 Departure day
The trip ends after breakfast.
From Siena, you can easily take a bus to Florence, which runs every 30 minutes, or book a private transfer (not included). You can also extend the trip with an extra day & night in Siena.
Accommodations
Choose between staying in a mix of 4 and 3 star hotels, or 3 star hotels throughout.
8 days/ 7 nights
| Night | Place | Accommodation |
|---|---|---|
| Night 1 | Florence | Hotel ***/**** |
| Night 2 | Florence | Hotel ***/**** |
| Night 3 | Greve in Chianti | Hotel ***/**** |
| Night 4 | Greve in Chianti | Hotel ***/**** |
| Night 5 | Radda in Chianti | Hotel ***/**** |
| Night 6 | Radda in Chianti | Hotel ***/**** |
| Night 7 | Siena | Hotel ***/**** |
5 days/ 4 nights
| Night | Place | Accommodation |
|---|---|---|
| Night 1 | Florence | Hotel ***/**** |
| Night 2 | Greve in Chianti | Hotel ***/**** |
| Night 3 | Radda in Chianti | Hotel ***/**** |
| Night 4 | Siena | Hotel ***/**** |
4 days/ 3 nights
| Night | Place | Accommodation |
|---|---|---|
| Night 1 | Florence | Hotel ***/**** |
| Night 2 | Greve in Chianti | Hotel ***/**** |
| Night 3 | Siena | Hotel ***/**** |
Route map
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