Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Flights
available
16.0Kg CO2e
Printed route
directions
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?
The walks traverse small gravel roads (strade bianche), footpaths, and mule tracks across hilly terrain. You'll pass through several small hamlets and larger villages. With Tuscany's hills covering nearly two-thirds of the region, expect frequent and sometimes steep ascents and descents. Reasonable fitness and confidence are recommended.
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.
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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.
Room upgrades: Please contact us for details.
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.
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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.
Room upgrades: Please contact us for details.
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.
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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.
Room upgrades: Please contact us for details.
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.
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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.
Room upgrades: Please contact us for details.
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.
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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.
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.
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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.
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.
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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.
After breakfast, departure from Siena
If you'd like to extend your trip with extra hotel nights we recommend: Hotel Chiusarelli, Siena; Hotel Park Palace, Florence.
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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.
MastercardVisaPoolHairdryerWiFiTVMinibarAirconSafe
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.
Room upgrades: Please contact us for details.
These tour prices are based on two people sharing. Single supplement from £330.
We can book your flights, protected by ATOL and ABTA. Please ask at time of enquiry.
If you choose a flight inclusive package with us, you will fly into Pisa airport. We can provide transfers from the airport, please contact us for details and prices.
We hold an ATOL License and are fully ABTA bonded, so you can book your flights with us in confidence. We can book most airlines and will advise you of your most convenient airport and flight options.
Flight prices vary massively and change quickly. At Headwater we will sell you your flights at the same price you can buy them yourself. We simply add £35 per person to cover your flight protection, to learn more please click here.
Subject to availability and dependent on service provider, please ask at time of enquiry and book early to avoid disappointment.
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Flights
available
16.0Kg CO2e
Printed route
directions
