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Italy: Tuscany

Wine & Walk in Chianti

Trip code: W07TU

Average customer rating 4.0 / 5(2 verified reviews)

Self-Guided Walking
7 nights hotel-to-hotel
Moderate
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

Explore the mesmerising heart of the Chianti Classic wine-growing area

Visit the breathtakingly beautiful World Heritage cities of Florence & Siena

Indulge in the delicious olive oils and fabulous cuisine of the Tuscan region

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Trip details

Beauty, relaxation, history and wine! Timeless Tuscany is quintessential Italy with its rolling hills dotted with cypress trees and hilltop towns perched high above. Incredible food prepared with passion and cities with so much culture it almost defies belief. Slow down and truly discover the people, villages and culture of Tuscany. You will be intrigued by roadside memorials from classical times, deserted medieval chapels, extraordinary villas and churches, and sleepy villages all drenched in golden Tuscan sunlight.

What's included

Included

  • 7 nights in 3-star and 4-star accommodation
  • All breakfasts and 1 evening meals
  • Headwater navigation app
  • Luggage transfers between hotels
  • Walk Transfers

Not included

  • Flights
  • Local taxes/fees
  • Travel insurance

Travel options

Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in Florence

Arrive in Florence

Arrive at your 4 star hotel located just a short walk from the historical heart of Florence, where you have time to relax in the pool before dinner.

You stay at Hotel Park Palace

Hotel Park Palace
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Hotel Park Palace

Florence

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Minibar
  • Other email access
  • Safe
  • Swimming pool
  • Television
  • Visa cards
  • Wifi access

The 4-star Hotel Park Palace is set in a historic Florentine style Villa surrounded by the Tuscan hills. It is located just outside the vibrant city of Florence for a more tranquil setting. A short 20-minute walk will take you right by the iconic Ponte Vecchio.

Relax and comfort are guaranteed here at Hotel Park Palace as the hotel features a large garden with outdoor pool and a reading lounge with fireplace furnished with tasteful antique pieces and Persian rugs.
The hotel has 26 spacious rooms featuring antique furniture and include TV with satellite channels.

During the summer months, a buffet breakfast is served al fresco on the terrace, enjoy the tranquil views of the large garden.

Day 2 · 14km/8.7miFlorence to Impruneta

Florence to Impruneta

Starting in the outskirts of Florence, pass Renaissance villas and traditional villages until you reach hills peppered with cypresses, olive groves, vineyards, villas and hilltop hamlets.

Elevation

Florence to Impruneta elevation profile

You stay at Hotel Bellavista

Hotel Bellavista
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Hotel Bellavista

Impruneta

  • Air conditioning
  • Hairdryers
  • Other email access
  • Safe
  • Television
  • Wifi access

This 3-star property has been run by the Becucci family for 4 generations, ever since 1906 when travellers would spend a night or two during their journeys between Florence and Siena.

The hotel has recently been restored in 2016 to combine the modern comforts to its original charm. It is located in the city centre of Impruneta and features a roof-garden with views over the main city square and the idyllic Tuscan countryside.
All rooms at Hotel Bellavista are decorated in traditional Tuscan style with terracotta floors and are equipped with an en suite bathroom, a hairdryer and satellite TV.

The on-site restaurant has beautiful views of the surrounding countryside and offers traditional Florentine cuisine. Dinner can be served on their panoramic terrace, on the veranda or in the garden.

Day 3 · 9km/5.6miUzzano Loop

Uzzano Loop

Start the day with a transfer to Greve in Chianti from where the walk leads uphill through the countryside and past the castle of Uzzano. Walk through woodland and on to the winery of Terreno. You’ll enjoy great views of the classic Chianti landscape with vineyards and olive groves all around, and the Appenine mountains in the distance.

Elevation

Uzzano Loop elevation profile

You stay at Albergo del Chianti

Albergo del Chianti
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Albergo del Chianti

Greve

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Other email access
  • Swimming pool
  • Television
  • Visa cards
  • Wifi access

Albergo del Chianti is set in the central square of Greve in Chianti, Piazza Matteotti, famous for its triangular shape. Thanks to its central position, you are only a stone’s throw away from Greve’s restaurants, bars and shops.

The hotel offers 22 comfortable rooms, all equipped with air conditioning, en suite bathroom and plasma-screen TV. It also benefits from a large outdoor salt-water swimming pool surrounded by a beautiful green garden with tables and deckchairs where you can just relax.

A buffet style breakfast is served here and it includes homemade cakes, scrambled eggs, cold meats, cheese and cereal.

Day 4 · —Free Day

Free Day

Greve is a popular destination and has an intriguing arcaded main square with plenty of cafes, shops, wine bars and museums to discover and you can visit the Cantine di Greve in Chianti where there are over 100 wines to be tasted! For an alternative walking option take the bus to nearby Panzano, a hilltop town and walk a loop through woodland and vineyards before returning by bus to Greve.

You stay at Albergo del Chianti

Albergo del Chianti
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Albergo del Chianti

Greve

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Other email access
  • Swimming pool
  • Television
  • Visa cards
  • Wifi access

Albergo del Chianti is set in the central square of Greve in Chianti, Piazza Matteotti, famous for its triangular shape. Thanks to its central position, you are only a stone’s throw away from Greve’s restaurants, bars and shops.

The hotel offers 22 comfortable rooms, all equipped with air conditioning, en suite bathroom and plasma-screen TV. It also benefits from a large outdoor salt-water swimming pool surrounded by a beautiful green garden with tables and deckchairs where you can just relax.

A buffet style breakfast is served here and it includes homemade cakes, scrambled eggs, cold meats, cheese and cereal.

Day 5 · 10km/6.2miMontefioralle Loop

Montefioralle Loop

A short yet spectacular circular walk – and the epitome of Tuscany. Today’s walk will take you to Montefioralle, which is a gem of a ‘borgo’ (village), perched in the hills and retaining its medieval flavour within its ancient walls. Transfer at the end of the day to your next stop, Radda in Chianti where you’ll spend two nights

Elevation

Montefioralle Loop elevation profile

You stay at Palazzo San Niccoló

Palazzo San Niccoló
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Palazzo San Niccoló

Radda in Chianti

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Other email access
  • Safe
  • Television
  • Visa cards
  • Wifi access

Set in the picturesque town of Radda in Chianti, nestled in the green hills of the Tuscan countryside. Palazzo San Niccolò is an elegant 4-star historic residence, beautifully decorated with Art Nouveau frescos and Tuscan cotto floors.

Rooms at San Niccolò are elegantly embellished with vintage accessories and decorations. All feature air conditioning and TV and all have en suite facilities with either a shower or bath.
You are welcome to unwind in the garden or enjoy a drink from the wine bar.

Breakfast is served in the small garden on the ground floor and a wide variety of food and homemade pastries is offered.

Day 6 · 16km/9.9miAt Radda in Chianti

At Radda in Chianti

Walking mostly on forest trails and gravel tracks in the hills outside Radda in Chianti passing Colle Bereto Winery, perhaps stop for a visit on your walk back. Continue on a loop through vineyards and olive groves to the walled, hilltop village of Vertine.

Elevation

At Radda in Chianti elevation profile

You stay at Palazzo San Niccoló

Palazzo San Niccoló
Image 1 of 4

Palazzo San Niccoló

Radda in Chianti

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Other email access
  • Safe
  • Television
  • Visa cards
  • Wifi access

Set in the picturesque town of Radda in Chianti, nestled in the green hills of the Tuscan countryside. Palazzo San Niccolò is an elegant 4-star historic residence, beautifully decorated with Art Nouveau frescos and Tuscan cotto floors.

Rooms at San Niccolò are elegantly embellished with vintage accessories and decorations. All feature air conditioning and TV and all have en suite facilities with either a shower or bath.
You are welcome to unwind in the garden or enjoy a drink from the wine bar.

Breakfast is served in the small garden on the ground floor and a wide variety of food and homemade pastries is offered.

Day 7 · 12km/7.5miRadda in Chianti to Gaiole in Chianti

Radda in Chianti to Gaiole in Chianti

Walking along Strade Bianche past vineyards you’ll reach the market town of Gaiole in Chianti – a former military stronghold, Gaiole is ringed by medieval castles and fortified abbeys.

A transfer will take you from Gaiole in Chianti to Siena, enjoy a tranquil and relaxing stroll in the pedestrianized city centre, discover its many alleys, churches and breathtaking views.

Elevation

Radda in Chianti to Gaiole in Chianti elevation profile

You stay at Hotel Chiusarelli

Hotel Chiusarelli exterior

Hotel Chiusarelli

Siena

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Other email access
  • Safe
  • Television
  • Visa cards
  • Wifi access

Hotel Chiusarelli is a 3-star neoclassical villa built in 1870 and recently renovated. It has managed to keep its original feel with frescoed rooms, while adding a more modern touch to the style and comforts.

This property is located in the centre of Siena, city of art and famous for the yearly Palio that still takes place to this day. From here, a short walk will take you to Piazza del Campo and the Duomo. Chiusarelli is set in a 3-storey building with no lift.

The hotel has 48 rooms decorated to a Neo Classical style featuring en suite bathrooms with bathtub or shower, fresh linen, hairdryer, safe deposit box, air conditioning/heater and TV.

A rich buffet breakfast is served here daily.

Day 8 · —Departure

Departure

After breakfast, departure from Siena

Extending your holiday

Hotel Chiusarelli exterior

Hotel Chiusarelli

Siena

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Other email access
  • Safe
  • Television
  • Visa cards
  • Wifi access

Hotel Chiusarelli is a 3-star neoclassical villa built in 1870 and recently renovated. It has managed to keep its original feel with frescoed rooms, while adding a more modern touch to the style and comforts.

This property is located in the centre of Siena, city of art and famous for the yearly Palio that still takes place to this day. From here, a short walk will take you to Piazza del Campo and the Duomo. Chiusarelli is set in a 3-storey building with no lift.

The hotel has 48 rooms decorated to a Neo Classical style featuring en suite bathrooms with bathtub or shower, fresh linen, hairdryer, safe deposit box, air conditioning/heater and TV.

A rich buffet breakfast is served here daily.

Hotel Park Palace
Image 1 of 5

Hotel Park Palace

Florence

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Minibar
  • Other email access
  • Safe
  • Swimming pool
  • Television
  • Visa cards
  • Wifi access

The 4-star Hotel Park Palace is set in a historic Florentine style Villa surrounded by the Tuscan hills. It is located just outside the vibrant city of Florence for a more tranquil setting. A short 20-minute walk will take you right by the iconic Ponte Vecchio.

Relax and comfort are guaranteed here at Hotel Park Palace as the hotel features a large garden with outdoor pool and a reading lounge with fireplace furnished with tasteful antique pieces and Persian rugs.
The hotel has 26 spacious rooms featuring antique furniture and include TV with satellite channels.

During the summer months, a buffet breakfast is served al fresco on the terrace, enjoy the tranquil views of the large garden.

What our travellers say

It is difficult for us to comment on the walks as because of my husband’s illness we only did half of the first walk and deviated from your walks on most of the other days but we felt the walks we did do could have been more interesting. We customised the holiday to some extent – we missed out the last walk and rearranged the taxi so we had more time for sightseeing in Siena; on another day we did a shorter walk following tourist signs from Greve, and at Radda we chose to do a shorter walk which we found at the Tourist Office. We added an extra night in Florence which gave us a full day there, and added a night in Pisa at the end of the holiday so for us this holiday was as much a sightseeing holiday as a walking holiday which worked well.

Greve was a lovely place and ideal for a rest day particularly as the hotel had a swimming pool. Our two nights there were perhaps the highlight of the walking holiday.

We would be grateful if you could pass on our thanks to Scape for arranging our rescue when my husband became ill halfway through the walk from Florence to Impruneta – for their helpfulness, courtesy and patience, and I know we put the taxi driver who made a detour to pick us up to some inconvenience. They were equally helpful when we rearranged taxi times later in the week.

Lesley Church

We really enjoyed the holiday just disappointed that the sixth walk involved quite a lot of the fifth walk.

Gareth Reynolds
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Positive impact

Carbon score for this trip

16.0

Kg CO₂e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more

From£1,309per person