The Hill-Top Towns of Tuscany

Landscapes immortalised by artists

Holiday Highlights

Historic towns | Intriguing Etruscan Volterra, fortified medieval San Gimignano, Renaissance Siena.
The rolling landscapes | Crowned by hill-top villages and dotted with idyllic churches.
The pace | A journey that embraces gentle days of exploration.
Local wines | Chianti Classico of course, but also reds and whites from San Gimignano.
The Hill-Top Towns of Tuscany. 7 nights
The Hill-Top Towns of Tuscany. 7 nights

Holiday information


A walking holiday via San Gimignano

Discover Tuscany’s rich culture and timeless countryside, stay in hill-top towns, including atmospheric San Gimignano, and savour the famous wines and beauty of the Chianti hills, while walking self-guided from one hotel to the next while your luggage is transported.
Nestling between the great art cities of Florence, Siena and Pisa, the Chianti hills are as famed for their beauty as for their dark red wines. Hill-top villages crown the rolling landscapes, and idyllic churches are dotted along the quiet paths. An extraordinary sense of history pervades the region, from the Etruscan town of Volterra to Siena’s wide Campo.

This walk takes you from Volterra through the Chianti vineyards and San Gimignano to the Sienese hills and magnificent Siena itself. The joy of the holiday is to feel the timelessness of the Tuscan countryside, and to discover the landscapes immortalised in the works of some of the world’s greatest artists.



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
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    °C 9 11 13 17 21 25 29 28 25 20 14 10
    mm 65 63 60 65 58 41 30 43 69 76 103 69
  • Arrival in Volterra
    Night 1: at Hotel San Lino or Hotel la Locanda (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.
  • Circular walk from Volterra: 9km, 4hrs; ascent 495m/descent 35m
    We suggest a short introductory walk to explore the soft rolling hills south of the town, by first following the route of an old rack-railway, before heading uphill across an evocative landscape that offers a striking profile of hill-top Volterra as you ascend gradually back to the town.
    Afterwards, or alternatively, spend some time exploring splendid Volterra. This atmospheric town boasts substantial Etruscan and Roman remains, as well as several museums and an art gallery. Stroll along Via Ricciarelli, where there are some fine tower houses, and visit one of the workshops where they still work alabaster. Take time, too, to admire the views from the ancient ramparts of the volcanic hills surrounding the town.
    Circular walk from Volterra: 9km
  • Volterra to San Gimignano: 12km, 4.5hrs; ascent 225m/descent 440m
    After a short transfer, you follow pleasant tracks and strade bianche across a couple of small valleys, through woodland and agricultural land as well as the village of San Donato, which boasts a lovely church. You pass numerous isolated poderi (farmsteads), once occupied by families of share-croppers who grew wheat, olives and grapes, and enjoy fine views across gently rolling hills to your destination, San Gimignano, where you spend two nights at the Hotel Bel Soggiorno.
    En route to San Gimignano
    Volterra to San Gimignano: 12km
  • Choice of circular walks from San Gimignano: 2.5km or 9km

    The town walls: 2.5km, 1hr; ascent/descent 95m
    For a good introduction to medieval San Gimignano, stroll around the town walls and look down on the charming streets lined with ancient houses and palaces. The walk itself takes about an hour, but allow longer for detours. In its heyday, San Gimignano boasted seventy towers; nowadays thirteen remain. On clear days it is well worth climbing the tallest of these, the tower belonging to the Palazzo del Popolo (pay locally), for splendid views of the area.

    Circular walk round San Gimignano: 9km, 3.5hrs; ascent/descent 255m
    For those wishing to walk a little further, we offer a circular route in the glorious countryside, which provides fantastic views towards the town's imposing towers.
    San Gimignano
    Circular walk round San Gimignano: 9km
  • San Gimignano to Colle Val d'Elsa: 10.5km, 4hrs; ascent 195m/descent 270m
    This beautiful walk takes you through much softer, archetypal Tuscan landscapes of olive groves and vineyards and across the small River Foci to the historic upper part of Colle Val d'Elsa, a fascinating town surrounded by ramparts. You stay for one night at either the Palazzo San Lorenzo in Colle Val d'Elsa itself, or at Relais della Rovere, a former abbey a couple of kilometres beyond the town.
    The route from San Gimignano to Colle Val d'Elsa
    San Gimignano to Colle Val d'Elsa: 10.5km
  • Colle Val d'Elsa to Siena: 18.5km, 7hrs; ascent 390m/descent 300m
    After a transfer to the fortified hamlet of Monteriggioni, you walk along a section of the Via Francigena, the ancient pilgrims' route between Canterbury and Rome, to arrive in Siena for your final two nights at the Hotel Garden. We can also offer the historic Palazzo Ravizza, a former noble residence set in lovely gardens close to the centre of Siena.
    Fortified Monteriggioni
    Colle Val d'Elsa to Siena: 18.5km
  • Explore Siena
    Today is devoted to sightseeing. 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.


You stay in four high-quality hotels of great character.

In some places, we work with more than one hotel, as shown below. All are hand-picked by us and, unless there is a price implication (in which case we will contact you to discuss your options), we will tell you which one we have booked for you on your booking confirmation.

In Siena, you have the choice of staying on the outskirts at the Hotel Garden or in the heart of the city at the Palazzo Ravizza (the latter is booked on a room-only basis). Please indicate your preference at the time of booking, when we will discuss any price implication with you. Whichever hotel you choose to stay at here, we recommend adding extra nights to further explore this Renaissance gem.

We also recommend an extra night in fascinating Volterra, which boasts several museums and galleries.

Options to extend or shorten 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: 01 April 2024 - 30 June 2024, 22 August 2024 - 31 October 2024, 01 April 2025 - 30 June 2025 & 21 August 2025 - 31 October 2025

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

    Starting Price Single room
    1 Apr - 20 May 2024 £1265 £370
    21 May - 23 Jun 2024 £1340 £380
    22 Aug - 30 Sep 2024 £1310 £370
    1 - 24 Oct 2024 £1215 £350
    1 Apr - 20 May 2025 £1320 £385
    21 May - 23 Jun 2025 £1395 £400
    21 Aug - 30 Sep 2025 £1365 £385
    1 - 24 Oct 2025 £1265 £365
    3rd & 4th person discount -£110 to -£114
    Single traveller supplement £110 to £114

    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.

    Deduct £32pp if your stay at Hotel Bel Soggiorno falls on a Wednesday as dinner is not included due to the restaurant's weekly closure.

    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)

    Hotel Bel Soggiorno, San Gimignano
    Panoramic view: 01 Apr - 30 Jun 2024 £13
    Panoramic view: 22 Aug - 31 Oct 2024 £13
    Panoramic view: 01 Apr - 30 Jun 2025 £14
    Panoramic view: 21 Aug - 31 Oct 2025 £14

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

    Hotel San Lino, Volterra (B&B) Double room Single room
    01 Apr - 30 Jun 2024 £66 £117
    22 Aug - 30 Sep 2024 £66 £117
    01 Oct - 31 Oct 2024 £59 £101
    01 Apr - 30 Jun 2025 £69 £122
    21 Aug - 30 Sep 2025 £69 £122
    01 Oct - 31 Oct 2025 £61 £105
    Hotel Bel Soggiorno, San Gimignano (with dinner) Double room Single room
    01 Apr - 30 Jun 2024 £160 £256
    22 Aug - 31 Oct 2024 £160 £256
    01 Apr - 30 Jun 2025 £170 £270
    21 Aug - 31 Oct 2025 £170 £270
    Deduct £29pp in 2023 or £32pp in 2024 if your stay at Hotel Bel Soggiorno falls on a Wednesday as dinner is not included due to the restaurant's weekly closure.
    Hotel Garden, Siena (B&B) Double room Single room
    01 Apr - 07 Apr 2024 £72 £115
    08 Apr - 30 Jun 2024 £105 £160
    22 Aug - 21 Oct 2024 £99 £149
    22 Oct - 31 Oct 2024 £72 £115
    01 Apr - 07 Apr 2025 £75 £120
    08 Apr - 30 Jun 2025 £109 £166
    21 Aug - 21 Oct 2025 £103 £155
    22 Oct - 31 Oct 2025 £75 £120
    Pisa, Bologna or Florence
    As an alternative to flying, we can arrange rail travel from London

    Travelling from the UK

    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Milan or Rome.  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
    Nottingham East Midlands - Pisa Ryanair 
    Outward route Airline
    Edinburgh - Bologna Ryanair 
    Edinburgh - Bologna (via Amsterdam Schiphol) KLM 
    Edinburgh - Florence British Airways 
    Edinburgh - Pisa Ryanair 
    Outward route Airline
    Glasgow - Bologna (via Amsterdam Schiphol) KLM 
    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 - Bologna (via Düsseldorf) Eurowings 
    Heathrow - Florence British Airways 
    Heathrow - Pisa British Airways 
    Outward route Airline
    Luton - Bologna Ryanair 
    Luton - Florence Vueling 
    Luton - Pisa easyJet 
    Outward route Airline
    Stansted - Bologna Ryanair 
    Stansted - Pisa Ryanair 
    Outward route Airline
    Manchester - Bologna Ryanair 
    Manchester - Bologna (via Frankfurt) Lufthansa 
    Manchester - Florence British Airways 
    Manchester - Pisa easyJet,  jet2,  Ryanair 
    Outward route Airline
    Newcastle - Bologna (via Amsterdam Schiphol) KLM 
    Newcastle - Florence (via Amsterdam Schiphol) Air France 
    Newcastle - Florence (via Paris) Air France 
    Newcastle - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Teesside International - Pisa (via Amsterdam Schiphol) KLM 
    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Milan or 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 for any of the options listed above. We charge £35 per person for our flight booking service. 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.

    Where a price range is given, the price you pay depends on your date of travel.

    Connecting travel options - flying via Bologna

    Outward route Price per person Latest flight
    arrival time
    rail Bologna Centrale to Florence SMN (0h45), taxi Florence SMN to hotel (1h30) £112-£116 1700
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h10, pay locally), rail Siena to Bologna Centrale (3h) £44-£46 1400

    Connecting travel options - flying via Florence

    Outward route Price per person Latest flight
    arrival time
    direct taxi Florence airport to hotel (1h30) £96-£100 flexible
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h10, pay locally), rail Siena to Florence SMN (1h35) £12 1300

    Connecting travel options - flying via Pisa

    Outward route Price per person Latest flight
    arrival time
    direct taxi Pisa airport to hotel (1h15) £69-£72 flexible
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h10, pay locally), rail Siena to Pisa Centrale (2h15) £13-£14 1200
What is included
  • 7 nights
  • 3 dinners
    7 breakfasts
  • luggage transported
  • route notes and maps
  • GPS navigation
  • 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 A to B, 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.
  • Yes, prior to going on holiday you will be able to download GPX tracks so that you can follow your route on your smartphone or dedicated GPS device if you wish. It’s entirely up to you whether or not you use them – our detailed, step-by-step route notes remain the principal means of guiding you from A to B – but we provide them as a secondary means of navigation for additional reassurance when walking.
  • We can book a wide range of routes from the UK with a variety of airlines. 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. The fee for this service is £35 per person (£15 for children aged 2-11). 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 us to discuss your plans.
  • We can’t book flights that originate outside the UK, but if you wanted to 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 incur a five or six-figure bill.

    Many insurers offer travel insurance (you can find details on our insurance page of a policy that you may like to consider if you are a UK resident), but you do need to make sure that you’re covered for medical emergencies – including falling ill with Covid-19 while on holiday – and repatriation. We also recommend that you are covered for other eventualities, such as cancellation and loss of luggage and passports.

    When you purchase a policy, be sure to check that it covers the activities you'll be doing on holiday and that it is adequate for your own individual needs.
  • 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 (please note, however, that a new travel authorisation system is being introduced). 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 the Travel Health Pro website. You must make sure you have adequate insurance cover for illness, accidents and repatriation (see the insurance question). You should also apply for a Global Health Insurance Card (GHIC) if your EHIC has expired (if you have a still-valid EHIC, you can use this until it expires).
  • 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.
  • For information on the practicalities of travel now that the UK is no longer part of the European Union, visit
  • The UK Foreign, Commonwealth & Development Office (FCDO) 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.
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