Wine & Walk in Chianti

0044 1606 720199

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  • Holiday code
    W07TU
  • Holiday type
    Self-guided walking
  • Duration
    7 nights
  • Accommodation
    hotel-to-hotel
    and
  • Activity level
  • From $2150per person, tour only
  • Departure months
    JFMAMJJASOND
  • What your holiday price includes
  • 7 nights hotel-to-hotel accommodation in a mix of and hotels
  • All breakfasts and 1 evening meal
  • Comprehensive route directions
  • Luggage transfers between hotels
  • GPX files
  • Walk Transfers
  • Optional Upgrades
  • Suitable for
  • Solo travellers
  • Couples
  • Excellent choice for
  • Food lovers, wine lovers, art & history

Italy: Tuscany

Wine & Walk in Chianti

  • 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

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.

Our 7-night self-guided holiday leads you through the mesmerising heart of Chianti Classico wine-growing region. Starting in the Renaissance city of Florence, with its centuries of history, art and culture. Everywhere you turn you are surrounded by extraordinary artistic and architectural masterpieces. Walk through beautiful vineyards where the world-famous Chianti wines have been produced for over 2,000 years. It is from this area alone that Chianti is able to boast its black-rooster seal, 'gallo nero' and you will be able to enjoy plenty of these on the way! Indulge in the delicious food and olive oils of the heart of rural Tuscany as you stay in welcoming characterful hotels. Your last night is spent in the medieval city of Siena dominated by its imposing Piazza del Campo. Take a step back in time as you wander its narrow streets, the perfect end to your Tuscan adventure!

With so much to see, why not have a few extra days to explore the World Heritage cities of Florence and Siena?



We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com



We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: 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 (breakfast included)

Day 2: Florence to Impruneta (14km/8.7mi)

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.
You stay at Hotel Bellavista (breakfast and evening meal)

Day 3: Uzzano Loop (12km/7.5mi)

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.
You stay at Albergo del Chianti (breakfast included)

Day 4: 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 (breakfast included)

Day 5: Montefioralle Loop (10km/6.2mi)

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
You stay at Palazzo San Niccoló (breakfast included)

Day 6: At Radda in Chianti (16km/9.9mi)

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.
You stay at Palazzo San Niccoló (breakfast included)

Day 7: Radda in Chainti to Gaiole in Chianti (12km/7.5mi)

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.
You stay at Hotel Chiusarelli (breakfast included)

Day 8: Departure

After breakfast, departure from Siena

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Park Palace, Florence

Swimming Pool IconHair dryer icon NEARBY:

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.


Extra nights: Please contact us for details.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Bellavista, Impruneta

Hair dryer icon NEARBY:

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.


Extra nights: Please contact us for details.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Albergo del Chianti, Greve

Swimming Pool IconHair dryer icon NEARBY:

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.


Extra nights: Please contact us for details.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Palazzo San Niccoló, Radda in Chianti

Hair dryer icon NEARBY: Swimming Pool Icon

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.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Chiusarelli, Siena

Hair dryer icon NEARBY:

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.


Extra nights: Please contact us for details.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Park Palace, Florence

Swimming Pool IconHair dryer icon NEARBY:

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.


Extra nights: Please contact us for details.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Chiusarelli, Siena

Hair dryer icon NEARBY:

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.


Extra nights: Please contact us for details.

Travel

Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.

Reviews

Here at Headwater we thrive on feedback and pride ourselves on our excellent customer service. Below is a small selection of reviews we've received from our satisfied customers.


05/02/2024

Helpful and attentive.


22/11/2023

Lauren couldn't have been more helpful. But then, I have always found Headwater's customer management good. I think they employ people who like helping customers. For a travel company, that's a pretty sensible place to start.


Julie , 22/11/2023

It was excellent, I couldn’t fault it. Both the ladies I spoke to were extremely helpful and friendly when I was enquiring and booking my holiday. They dealt extremely well with any questions or queries I had. We have had three most enjoyable cycling holidays before with Headwater.


//

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

This 7 night self-guided walking holiday includes:

Hotel-to-hotel accommodation in a mix of and hotels

All breakfasts and 1 evening meal

Comprehensive route directions provided prior to departure

Luggage transfers between hotels

GPX files

Walk Transfers


How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

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20th Oct 2024 US$2195 Tour only: US$2195 Check availability
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21st Oct 2024 US$2195 Tour only: US$2195 Check availability
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31st Oct 2024 US$2195 Tour only: US$2195 Check availability
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DepartingTour only Prices  
1st Apr 2025 US$2330 Tour only: US$2330 Check availability
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1st May 2025 US$2510 Tour only: US$2510 Check availability
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31st May 2025 US$2510 Tour only: US$2510 Check availability
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1st Jun 2025 US$2510 Tour only: US$2510 Check availability
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30th Jun 2025 US$2510 Tour only: US$2510 Check availability
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1st Jul 2025 US$2330 Tour only: US$2330 Check availability
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1st Sep 2025 US$2510 Tour only: US$2510 Check availability
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30th Sep 2025 US$2510 Tour only: US$2510 Check availability
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1st Oct 2025 US$2330 Tour only: US$2330 Check availability
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3rd Oct 2025 US$2330 Tour only: US$2330 Check availability
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19th Oct 2025 US$2330 Tour only: US$2330 Check availability
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20th Oct 2025 US$2330 Tour only: US$2330 Check availability
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21st Oct 2025 US$2330 Tour only: US$2330 Check availability
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22nd Oct 2025 US$2330 Tour only: US$2330 Check availability
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23rd Oct 2025 US$2330 Tour only: US$2330 Check availability
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24th Oct 2025 US$2330 Tour only: US$2330 Check availability
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25th Oct 2025 US$2330 Tour only: US$2330 Check availability
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26th Oct 2025 US$2330 Tour only: US$2330 Check availability
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27th Oct 2025 US$2330 Tour only: US$2330 Check availability
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28th Oct 2025 US$2330 Tour only: US$2330 Check availability
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29th Oct 2025 US$2330 Tour only: US$2330 Check availability
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30th Oct 2025 US$2330 Tour only: US$2330 Check availability
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31st Oct 2025 US$2330 Tour only: US$2330 Check availability
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The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Solo travellers
Please call for details and prices

Children
Please contact us for child prices.

Holiday type
Self-guided walking Managed locally by Headwater appointed agent.

Departures
Daily Departures from 29th Apr 2024 to 31st Oct 2025, for 7 nights. All dates are subject to availability, please contact us to check.

Meals
All breakfasts and 1 evening meal

Tailor-made travel

This holiday does not include any flights or rail.

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.

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