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Through the Chianti Hills

Tuscany’s celebrated wine heartland
Explore the romantic and evocative landscapes of Tuscany on a journey which culminates in the magnificent city of Siena. Walk self-guided while your luggage is transported, staying in classic Chianti towns at welcoming, traditional hotels, where you can indulge in Tuscan cuisine and outstanding wines.
Through the Chianti Hills . 7 nights
Through the Chianti Hills . 7 nights

Holiday information


A walking holiday to Siena

The postcard-perfect Tuscan scenery between Florence and Siena is what dreams are made of. The rolling Chianti hills are carpeted with olive groves, vineyards and a patchwork of verdant green and mellow ochre fields; beautiful, hill-top farmhouses survey the landscape, and isolated cypress trees reach up towards the warming sun. The delicious and rustic Tuscan cuisine, and the region’s velvety red wines, complete the picture. What more could you wish for?
If the food, wine and landscapes weren't enough, on this holiday you also get to stay in one of the world’s greatest art cities, Siena, the jewel among the magical Renaissance cities of Tuscany and the perfect place to end your discovery of this fascinating region. First, though, you discover the delights of Chianti country, staying at traditional wayside inns and enjoying rewarding views over these alluring landscapes.

The Da Vinci road
Follow Kevin Rushby's journey through the Chianti Hills, where he finds gorgeous Tuscan villages and sublime food and wine, before reaching Siena just in time for the Palio horse race. Read the full article >


The key to Inntravel holidays is flexibility. You can start on almost any day of the week, and are free to add extra nights.
  • The average maximum daytime temperatures and monthly rainfall relate to the nearest weather station and are intended as a guide only.

    In the hills, temperatures are likely to be cooler than those shown above.
    Average temperatures and rainfall
      Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
    °C 9 11 14 18 23 26 30 29 26 20 14 10
    mm 69 67 71 69 67 51 35 60 73 77 114 76
  • Arrival in Greve in Chianti
    Night 1: at Albergo-Ristorante Verrazzano (the first of two nights here).
    As your first night’s accommodation is on the day of travel, Day 1 is your first day of exploration.
  • Circular walk from Greve in Chianti: 12km, 3.5hrs
    Greve is widely considered the gateway to the rest of the Chianti region, and as you venture beyond its historic centre and into the gently sloping olive and vine-clad hills beyond, you’ll soon understand why. Our first route explores these archetypal Tuscan landscapes, before looping back to Greve where you may like to sample some of the renowned local wines.
  • Greve in Chianti to Radda in Chianti: 21km, 7hrs
    After a 10-minute transfer, today you enjoy an epic route from Greve, crossing the highest part of the Chianti hills and taking in the remarkable fortified settlement of Volpaia. The castle of Volpaia was built by the Florentines in the 12th century to garrison the borders of the Sienese territory, while the church, with its sober Renaissance façade, is dedicated to St Eufrosinus, the evangeliser of Chianti. After exploring the town you continue to the village of Radda in Chianti for two nights at the elegant Relais Vignale.
    Approaching Volpaia on the route from Greve in Chianti to Radda in Chianti
  • Circular walk from Radda in Chianti: 13km, 4hrs
    Enjoy a circular walk via Castello d’Albola, where there is an opportunity for wine-tasting before returning to your hotel and spending the rest of the day by its inviting swimming pool.
  • Radda in Chianti to San Sano: 16km, 5hrs
    You continue south-east, passing the Romanesque church of San Giusto to reach the Hotel Residence San Sano, in the village of the same name.
  • San Sano to Siena: 18km, 5.5hrs to Villa Scacciapensieri; 21km, 6hrs to Palazzo Ravizza
    Today begins with a short transfer, after which you cross beautiful open rolling countryside as you gradually close in on Siena, its distinctive towers coming into view as you walk. As you approach the outskirts, a track and quiet country lane lead you towards the Villa Scacciapensieri.
    For those wishing to stay more centrally, a further walk (or taxi ride, if you choose) takes you uphill through the suburbs, passing beneath one of Siena’s medieval city gates to reach the historic centre where you stay at the Palazzo Ravizza.
  • Explore Siena
    Your last day is devoted to sightseeing: uncover Siena’s many Renaissance treasures using our specially devised self-guided walking tour. The centre of Sienese life is the delightful Campo, a piazza bordered on one side by the Palazzo Pubblico, which houses some splendid frescoes, including Lorenzetti's Effects of Good and Bad Government, and is topped by the Mangia Tower, which offers a superb panorama of the city. The cathedral is also well worth a visit (among its masterpieces are works by Jacopo della Quercia and Donatello), as are the Museo dell'Opera del Duomo and the Pinacoteca.
    Explore Siena


You stay in a pleasingly eclectic mix of hotels. In Siena, you have the choice of staying on the outskirts at the Villa Scacciapensieri or in the heart of the city at the Palazzo Ravizza. Please indicate your preference at the time of booking, when we will discuss any price implication with you. Wherever you choose to stay in Siena, we recommend adding an extra night in this Renaissance gem.

Extend your stay

Prices & travel options
All prices are in £ sterling (GBP). If you'd like to see what they equate to in your currency, use the converter. For general information on pricing, see the 'your holiday price explained' page.
Currency converter

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  • 7 nights: 07 April 2020 - 30 June 2020 & 22 August 2020 - 31 October 2020

    Start any day | End by latest date(s) shown above

    Starting Price Single room
    7 - 12 Apr 2020 £1045 £410
    13 - 26 Apr 2020 £1085 £385
    27 Apr - 21 May 2020 £1145 £435
    22 May - 11 Jun 2020 £1180 £445
    12 - 23 Jun 2020 £1230 £435
    22 - 29 Aug 2020 £1145 £435
    30 Aug - 2 Sep 2020 £1180 £445
    3 Sep - 1 Oct 2020 £1230 £435
    2 - 10 Oct 2020 £1165 £440
    11 - 24 Oct 2020 £1085 £385
    3rd & 4th person discount -£80
    Single traveller supplement £80

    Includes accommodation, meals and services integral to the holiday as described, plus walking notes and maps, but no travel from the UK, nor any connecting travel from the airport unless stated below.

    Book your flights through us and we'll find the best route and times to suit you. Please contact us to find out more about our flight booking service. We can also book connecting travel - see below.

  • Room upgrades (£ per person per night)

    Relais Vignale, Radda in Chianti
    Deluxe: 09 Apr - 10 Apr 2020 £15
    Deluxe: 11 Apr - 12 Apr 2020 £20
    Deluxe: 13 Apr - 29 Apr 2020 £15
    Deluxe: 30 Apr - 30 Jun 2020 £27
    Deluxe: 22 Aug - 31 Aug 2020 £15
    Deluxe: 01 Sep - 31 Oct 2020 £27
    Hotel San Sano, San Sano
    Deluxe: 09 Apr - 30 Jun 2020 £20
    Deluxe: 22 Aug - 31 Oct 2020 £20
    Villa Scacciapensieri, Siena
    'Standard' suite: 09 Apr - 17 Apr 2020 £12
    'Standard' suite: 18 Apr - 16 Jun 2020 £7
    'Standard' suite: 17 Jun - 30 Jun 2020 £10
    'Standard' suite: 22 Aug - 07 Sep 2020 £7
    'Standard' suite: 08 Sep - 07 Oct 2020 £10
    'Standard' suite: 08 Oct - 15 Oct 2020 £7
    'Standard' suite: 16 Oct - 31 Oct 2020 £12

    Extra nights (£ per person per night) in a double or single room

    Relais Vignale, Radda in Chianti (B&B) Double room Single room
    09 Apr - 10 Apr 2020 £88 £174
    11 Apr - 12 Apr 2020 £116 £230
    13 Apr - 29 Apr 2020 £98 £192
    30 Apr - 30 Jun 2020 £116 £230
    22 Aug - 31 Aug 2020 £98 £192
    01 Sep - 31 Oct 2020 £116 £230
    Villa Scacciapensieri, Siena (B&B) Double room Single room
    09 Apr - 11 Apr 2020 £68 £88
    12 Apr - 12 Apr 2020 £128 £128
    13 Apr - 17 Apr 2020 £68 £88
    18 Apr - 16 Jun 2020 £106 £112
    17 Jun - 30 Jun 2020 £128 £128
    22 Aug - 07 Sep 2020 £106 £112
    08 Sep - 07 Oct 2020 £128 £128
    08 Oct - 15 Oct 2020 £106 £112
    16 Oct - 31 Oct 2020 £68 £88
    Florence, Bologna, Pisa

    Travelling from the UK

    Travelling from outside the UK

    If you are flying from outside Europe,  you may need to fly to an airport not listed. To discuss onward connecting travel to the start of your holiday, please contact us.

    Outward route Airline
    Aberdeen - Bologna (via Amsterdam Schiphol) KLM 
    Aberdeen - Bologna (via Paris) Air France 
    Aberdeen - Florence (via Amsterdam Schiphol) KLM 
    Aberdeen - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Birmingham - Bologna (via Amsterdam Schiphol) KLM 
    Birmingham - Bologna (via Frankfurt) Lufthansa 
    Birmingham - Pisa jet2 
    Birmingham - Pisa (via Munich) Lufthansa 
    Outward route Airline
    Bristol - Bologna Ryanair 
    Bristol - Florence British Airways 
    Bristol - Pisa easyJet 
    Outward route Airline
    Durham Tees Valley - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Nottingham East Midlands - Pisa jet2,  Ryanair 
    Outward route Airline
    Edinburgh - Bologna Ryanair 
    Edinburgh - Florence British Airways 
    Edinburgh - Pisa Ryanair 
    Outward route Airline
    Glasgow Prestwick - Pisa Ryanair 
    Outward route Airline
    Humberside - Bologna (via Amsterdam Schiphol) KLM 
    Humberside - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Leeds Bradford - Bologna (via Amsterdam Schiphol) KLM 
    Leeds Bradford - Pisa Ryanair 
    Leeds Bradford - Pisa jet2 
    Leeds Bradford - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Liverpool - Pisa Ryanair 
    Outward route Airline
    London City - Florence Air France,  British Airways 
    Outward route Airline
    Gatwick - Bologna easyJet 
    Gatwick - Florence British Airways,  Vueling 
    Gatwick - Pisa British Airways,  easyJet 
    Outward route Airline
    Heathrow - Bologna British Airways 
    Heathrow - Pisa British Airways 
    Outward route Airline
    Luton - Florence Vueling 
    Luton - Pisa easyJet 
    Outward route Airline
    Stansted - Bologna Ryanair 
    Stansted - Pisa Ryanair 
    Outward route Airline
    Manchester - Bologna Ryanair 
    Manchester - Florence British Airways 
    Manchester - Pisa easyJet,  jet2,  Ryanair 
    Outward route Airline
    Newcastle - Pisa jet2 
    Travelling from outside the UK

    If you are flying from outside Europe,  you may need to fly to an airport not listed. To discuss onward connecting travel to the start of your holiday, please contact us.

    This list of flight options should be used as a guide only, and you should check each airline’s website for current routes, frequency and schedules. Not all flights operate daily, and may not run for the entire season. You should also heed the latest flight arrival time and earliest flight departure time stated in the connecting travel section, as it may not be possible to arrange connecting travel outside these times. Please do not book your flights until we have confirmed your accommodation to you. Alternatively, our expert reservations team will be happy to offer advice and to make flight bookings for you. We charge £35 per person for our flight booking service (£60 for India and Nepal). Your flights are then covered by our package-booking conditions, which give you greater protection in the event of delay or cancellation, as well as providing ATOL cover.

  • Prices below are based on 2 people travelling together. If you are travelling solo or as a party of 3 or more and our arrangements include a taxi, please contact us for prices; additional passengers often pay less.

    Unless otherwise stated, connecting travel by rail or bus tends to be from the city centre station, rather than from its airport, and connections between the two should be paid for locally.

    Connecting travel options - flying via Pisa

    Outward route Price per person Latest flight
    arrival time
    rail Pisa Centrale to Florence SMN (1h15), bus Florence bus station to Greve (0h55, pay locally) £10 1330
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h05, pay locally), rail Siena to Pisa Centrale (1h45/2h) £12 1230

    Connecting travel options - flying via Bologna

    Outward route Price per person Latest flight
    arrival time
    rail Bologna Centrale to Florence SMN (0h40), bus Florence bus station to Greve (0h55, pay locally) £33 1400
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h05, pay locally), rail Siena to Bologna Centrale (3h) £44 1400

    Connecting travel options - flying via Florence

    Outward route Price per person Latest flight
    arrival time
    bus Florence bus station to Greve (0h55) pay locally 1500
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h05, pay locally), rail Siena to Florence SMN (1h35) £11 1300
What is included
  • 7 nights
  • 3 dinners
    1 picnic
    7 breakfasts
  • luggage transported
  • route notes and maps
  • notes for city walking tours
  • transfers on days 2 & 5

If you've experienced this holiday first hand, why not write a review?

We are keen for as many customers as possible to review their holiday. To make it easier to do so, we include a specific review section on our post-holiday questionnaire, and this is what we publish here, unedited. Read our full review policy >



If you have any questions relating to this or any other Inntravel holiday, our friendly travel experts will be happy to help. You might also find our General FAQs section helpful.
  • We’ll send you route notes and maps 2-3 weeks before your holiday. The route notes not only contain directions to get from hotel to hotel, but also include practical information about places of interest and eateries along each route, plus cultural information about the area. If/when you are moving between hotels, you leave your luggage in reception as you leave, and it will be transferred ahead to your next accommodation, meaning that all you need to take with you are a camera, sun cream, drinks, food and waterproofs.

    For more detailed information, see our walking holidays in Europe page.
  • We can book a wide range of airlines and routes from the UK. As well as being more convenient for you to book all elements of your holiday together, it also means that we’ll accept liability for your travel arrangements, so if things go wrong, such as the airline going bust, we’ll make suitable alternative arrangements for you. For Europe and Morocco, there’s a £35 booking fee per person (£15 for children aged 2-11). For India and Nepal, the booking fee is £60 per person. More information on flights >
  • Absolutely! We are experts in tailored rail travel. Making use of sleeper trains or stopovers in cities along the route, we can get you from London to virtually anywhere in mainland Europe. We can even make arrangements to Mallorca, Sicily and Norway with a combination of ferries and rail. Please contact Abi and Lizzie to discuss your plans.
  • We can’t book flights that originate outside the UK, but if you wanted book your own flights to London (or elsewhere in the UK), we can make all onward travel arrangements (including flights) from there. Alternatively, if you are booking your own flights to an airport in continental Europe that’s appropriate for your holiday, we can book onward rail travel and/or taxis. More information about how we can tailor holidays for customers outside the UK >
  • Since our holidays are self-guided, we recommend calling us for a chat about your plans before making a booking, especially if it’s the first time you’ve booked with us.
    The price panel shows the supplement for a single room and also the single traveller charge (this covers (luggage) transfers and other costs which are usually shared between two people).
  • Once you’ve decided on your exact itinerary (our travel experts will be happy to offer advice), you need to provide us with your party’s details, either by phone or via our booking form. At this point we also ask you to pay a deposit so that we can secure a room for you immediately on confirming availability with the hotel(s). If it turns out that we can’t secure the accommodation for the holiday you’ve requested, or offer an acceptable alternative, we’ll refund your deposit promptly and in full. After booking your accommodation and other key elements, we'll then book your travel (or you can do so if you’re making your own arrangements) and send you a Booking Confirmation and Invoice.

    More information about the booking process >
    Information about accommodation, general practicalities and more >
    Booking conditions >
  • Yes, it’s something we insist on, even for holidays in the UK. The vast majority of holidays go smoothly, but when things go wrong, it can be expensive to put them right. Buying a new pair of walking boots after your suitcase is stolen mightn’t seem so bad, but the bill for being airlifted down from a mountain with a broken leg or flown home while still recovering from an illness or accident can cost tens of thousands of pounds.

    You don’t have to buy our travel insurance policy (if you live outside Europe you’ll definitely need to make your own arrangements, as the policy is only for UK and EU residents), but you do need to make sure that you’re covered for medical emergencies and repatriation. We also recommend that you are covered for other eventualities, such as cancellation and loss of luggage and passports.

    We'll ask you for the details of your alternative policy (insurer, policy number and medical emergency phone number) so that we can help out if the worst happens while you are on holiday. It's up to you, though, to check that your policy covers the activities you'll be doing on holiday and that it is adequate for your own individual needs; we don't check alternative policies.
  • It is your responsibility to ensure you are in possession of the correct travel documents, with the correct validity. If you’re a UK citizen, you need a full British passport to travel to Italy, but not a visa. If you are a citizen of another country, you’ll need to check requirements with the national embassy or your own consulate.

    Current information regarding vaccinations and travel health advice for UK citizens can be found through and the National Travel Health Network and Centre (NaTHNaC). You must make sure you have adequate insurance cover for illness, accidents and repatriation (see the insurance question). UK citizens should also obtain a European Health Insurance Card (EHIC) by applying at a Post Office or at The EHIC allows reciprocal health care but should not be seen as a substitute for travel insurance.
  • The principal official language is Italian, though some regions have a second official language, such as South Tyrol, where German is widely spoken. The currency is the Euro. Italian time is GMT/UTC + 1. It uses Daylight Saving Time, so in summer is on BST + 1.
  • At Inntravel we work in close partnership with our hoteliers, taxi drivers and other local suppliers to provide our self-guided holidays directly to you. We are entirely confident that you will continue to receive the usual warm welcome from them when the UK withdraws from the European Union (EU).

    It currently seems highly likely the UK’s withdrawal from the EU will take place on 31 January 2020, at which point the UK will enter a minimum 11-month transition period through to the end of December 2020. During this transition period there will be absolutely no changes to current arrangements for UK citizens travelling to an EU destination, so you can book your 2020 holiday certain that there will be no disruptions or complications caused by Brexit.
  • The UK Foreign and Commonwealth Office (FCO) provides up-to-date, country-by-country travel advice, as well as information on security, local laws, passports and visas for UK citizens.
    If you live outside the UK, see our essential travel information page for a list of relevant websites.
  • You are the best judge of your child’s/children’s capabilities. We are happy to take bookings for families of older children/teenagers if they walk regularly, love the outdoors and are comfortable with the distances and ascent/descent involved. Please note that the bedrooms at most of the accommodation we use will normally only sleep a maximum of 3 people, and sometimes only 2.
Last fetch time is : 5/26/2020 10:31:47 PM