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The Essence of Tuscany

Tranquil trails south of Siena
Discover a quintessentially Tuscan land of olive groves and cypress trees as you walk self-guided from one characterful hotel to the next while your luggage is transported. Savour superlative wines and hearty Tuscan cooking, and enjoy stays in medieval Montalcino and Renaissance Pienza.
The Essence of Tuscany . 7 nights
The Essence of Tuscany . 7 nights

Holiday information


A walking holiday in southern Tuscany

Cypresses, olive groves, honey-coloured stone farmhouses, fields of sunflowers – the undulating landscapes south of Siena hold a special allure. Indeed, this is a timeless region of great natural beauty and wide-open spaces, and it is a joy to walk amid these tranquil landscapes as our route leads you through archetypal Tuscan landscapes with stays at characterful rural hotels.
Your destination, which you reach via the beautiful Val d'Orcia, is the Renaissance city of Pienza, the birthplace of Pope Pius II, who dreamed of transforming it into a utopian city. His efforts may be admired in the precious architectural scenario designed by Bernardo Rossellino from 1459 to 1462. The main square, the cathedral (and its museum) and the Palazzo Piccolomini appear as if unaffected by time. The groomed countryside is also home to the tiny hamlet of Monticchiello, where a reign of silence and mystery remain. Here, you will be able to sample the olive oil and slightly spicy pecorino cheese after your rewarding walk.


The key to Inntravel holidays is flexibility. You can start on the day of your choice, 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.
    Average temperatures and rainfall
      Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
    °C 8 9 12 15 20 24 28 28 24 18 13 9
    mm 57 58 57 62 59 43 33 46 61 73 90 68
  • Arrival in Pieve a Salti
    Night 1: at Fattoria Pieve a Salti (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 walking.
  • Linear walk from Pieve a Salti, returning by taxi: 11km, 4.5hrs; ascent 375m/descent 340m
    We recommend that you walk to the Abbey of Monte Oliveto Maggiore, surrounded by cypresses and famous for its early Renaissance frescoes. The first part of the walk leads past a string of small farms to the panoramic hill-top village of Chiusure, from where the path threads its way through woodland and over eroding cliffs to the abbey’s secluded location. After lunch in one of the eateries, return by taxi (pay locally). Alternatively, you could spend the day in the Fattoria’s spa or by the pool, or hire mountain bikes to explore on two wheels (pay locally).
    The Abbey of Monte Oliveto Maggiore
  • Pieve a Salti to Montalcino: 18.5km, 7hrs; ascent 635m/descent 230m
    Today's walk is varied and rewarding. After a short transfer to the historic town of Buonconvento, you strike out past fields of sunflowers. The Crete Senesi begins to open out, stretching towards your destination, Montalcino, with Mount Amiata's extinct volcanic cone as a backdrop. Suddenly, after passing through a wildlife reserve in which you may glimpse roe deer and wild boar, the rolling farmland gives way to vineyards and olive groves which stretch as far as the eye can see. A final steady, steep, ascent is rewarded with arrival in the medieval streets of Montalcino, and your hotel for the next two nights, the Hotel dei Capitani.
    Route from Pieve a Salti to Montalcino
  • Linear walk from Montalcino, returning by bus: 11.5km, 4.5hrs; ascent 310m/descent 470m
    Follow paths through the Brunello vineyards, olive groves and pastures to reach the Abbey of Sant’Antimo, one of the most outstanding examples of Romanesque monastic architecture in Italy. From here, you return by bus (pay locally) to Montalcino, with the rest of the day free to explore. Among this famous wine town’s highlights are a pentagonal 14th-century fortress, the beautiful Palazzo Comunale, and the Museo Civico with its fine collection of paintings. It’s also worth taking a stroll along the ramparts for far-reaching views.
    Towards the Abbey of Sant'Antimo on the route from Montalcino
  • Montalcino to San Quirico: 13.5km, 5hrs; ascent 465m/descent 400m
    You start the day with a transfer to Castelnuovo dell'Abate. From here, peaceful strade bianche (gravelled roads), farm tracks and woodland trails cross several small hills and remote countryside as they lead down to the winding River d'Orcia to enter one of Tuscany’s most beautiful valleys. There is a distinctly Mediterranean feel to this enchanting route and its flora, and in clear weather you enjoy views once more of Monte Amiata. Take time on arrival to stroll through San Quirico's attractive medieval centre, where you spend a night at the Relais Palazzo del Capitano.
  • San Quirico to Pienza: 14km, 5.5hrs; ascent 430m/descent 355m
    Your route heads out of San Quirico to reach the tiny hamlet of Vignoni, which sits on a small promontory, dominated by several towers. Quiet strade bianche continue from here across open rolling countryside, offering spectacular views towards Pienza, your destination. It was in Pienza that Pope Pius II was born, and he dreamed of transforming it into a utopian city. You spend your final two nights here at the Hotel Il Chiostro di Pienza.
    Farm track on the route from San Quirico to Pienza
  • Linear walk from Pienza, returning by bus: 15km, 6hrs; ascent 575m/descent 460m
    You may well want to spend your last day exploring Pienza to appreciate the magnificent architecture. Alternatively, a final, very varied walk crosses rolling hills to reach the tiny hill-top medieval hamlet of Monticchiello – one of Tuscany’s most beautiful stone-built hamlets. You then continue along little-used trails through light woodland to reach the hill-top town of Montepulciano, another jewel of the region, via the magnificent Renaissance church of San Biagio. Return to Pienza by bus (pay locally) once you have finished exploring.
    Approaching Montepulciano


Your comfortable accommodation is varied and characterful.

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.
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  • 7 nights: 05 April 2020 - 30 June 2020 & 25 August 2020 - 31 October 2020

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

    Starting Price Single room
    5 - 13 Apr 2020 £895 £325
    14 - 23 Apr 2020 £845 £275
    24 Apr - 21 May 2020 £895 £325
    22 May - 23 Jun 2020 £935 £330
    25 Aug - 30 Sep 2020 £935 £330
    1 - 24 Oct 2020 £920 £325
    3rd & 4th person discount -£55
    Single traveller supplement £55

    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)

    Il Chiostro di Pienza,
    Suite: 05 Apr - 30 Jun 2020 £10
    Suite: 25 Aug - 31 Oct 2020 £10

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

    Hotel dei Capitani, Montalcino (B&B) Double room Single room
    05 Apr - 30 Jun 2020 £72 £124
    25 Aug - 31 Oct 2020 £72 £124
    Relais Palazzo del Capitano, San Quirico d'Orcia (B&B) Double room Single room
    05 Apr - 30 Jun 2020 £72 £143
    25 Aug - 31 Oct 2020 £72 £143
    Il Chiostro di Pienza, (B&B) Double room Single room
    05 Apr - 09 Apr 2020 £57 £62
    10 Apr - 18 Apr 2020 £82 £112
    19 Apr - 29 Apr 2020 £57 £62
    30 Apr - 01 May 2020 £82 £112
    02 May - 30 May 2020 £78 £103
    31 May - 02 Jun 2020 £82 £112
    03 Jun - 30 Jun 2020 £78 £103
    25 Aug - 31 Aug 2020 £68 £83
    01 Sep - 30 Oct 2020 £78 £103
    31 Oct - 31 Oct 2020 £82 £112
    Pisa, Rome

    Travelling from the UK

    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Rome. To discuss onward connecting travel to the start of your holiday, please contact us.

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

    If you are flying from outside Europe,  we recommend flying via Rome. 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 Buonconvento (2h- 3h), hotel transfer from Buonconvento station (0h10) £25 1500
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Buonconvento (0h30), rail Buonconvento to Pisa Centrale (2h15 - 3h) £50 1300

    Connecting travel options - flying via Rome (Fiumicino and Ciampano)

    Outward route Price per person Latest flight
    arrival time
    rail Rome Termini to Chiusi (1h50/2h), taxi to hotel (1h) £78 1500
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Chiusi (1h), rail Chiusi Rome Termini (1h50/2h) £60 1500
What is included
  • 7 nights
  • 3 dinners
    3 picnics
    7 breakfasts
  • luggage transported
  • route notes and maps
  • transfers on days 2 & 4

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 : 7/10/2020 1:16:44 PM