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Hill-Top Towns of Tuscany with San Gimignano - Short Break

Quintessential Tuscan landscapes
 
Experience the rich culture and delicious Tuscan cuisine as you take gentle walks through archetypal Tuscan landscapes on this self-guided, hotel-to-hotel walking holiday, with your luggage transported as you go.
What is included
  • 4 nights
  • 1 dinner
    4 breakfasts
  • luggage transported
  • route notes and maps
  • GPS navigation
  • transfer on day 2
  • taxi from Pisa airport
    rail back to Pisa
  • Hill-Top Towns of Tuscany with San Gimignano - Short Break
    Quintessential Tuscan landscapes
  • San Gimignano
  • Idyllic scenery
  • Colle Val d'Elsa
  • Monteriggioni
  • Do not miss Siena's beautiful Duomo
  • Il Campo, Siena
What is included
  • 4 nights
  • 1 dinner
    4 breakfasts
  • luggage transported
  • route notes and maps
  • GPS navigation
  • transfer on day 2
  • taxi from Pisa airport
    rail back to Pisa
 

Holiday information

 

A walking break in Tuscany

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 San Gimignano's imposing medieval towers to Siena’s wide Campo.
Enjoy wonderful walking through vineyards, rolling hills and timeless woodland. Tuscany's magical countryside and the marvellous food and wine will be revealed in all their richness on this unique journey through scenery immortalised in the works of many great artists.

 

Itinerary

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 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 San Gimignano
    Night 1: at Il Bel Soggiorno (where you spend one night).
    As your first night’s accommodation is on the day of travel, Day 1 is your first day of walking.
  • San Gimignano to Colle Val d'Elsa: 10.5km, 4hrs; ascent 195m/descent 270m
    This is a scenic walk which leads you through archetypal Tuscan countryside of olive groves and vineyards, and across the River Foci, to another fascinating hill town, Colle Val d'Elsa, surrounded by ramparts. There are classic views of San Gimignano and its striking towers as you leave it behind. 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: 17km, 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. You descend through farmland to reach Siena, where your hotel for your last two nights is the historic Palazzo Ravizza, a Renaissance mansion close to the historic centre.
    Fortified Monteriggioni
    Colle Val d'Elsa to Siena: 18.5km
  • Explore Siena
    At the heart of this enchanting city is the incomparable square, the Campo, which is the centre of Sienese life. The cathedral is also magnificent, its masterpieces including works by Donatello, Ghiberti and Jacopo della Quercia. As in all Tuscan towns, just walking around is a great pleasure, and you will discover ancient gates, parts of the city wall and a wide selection of bars and restaurants.
    Explore Siena
 

Accommodation

Three high-quality hotels make this an enjoyable break.

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 we recommend adding extra nights to further explore 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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  • 4 nights: 01 April 2025 - 30 June 2025, 21 August 2025 - 30 November 2025, 01 April 2026 - 30 June 2026 & 21 August 2026 - 30 November 2026

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

    Starting Price Single room
    1 - 30 Apr 2025 £910 £240
    1 May - 30 Jun 2025 £990 £275
    21 Aug - 10 Sep 2025 £955 £270
    11 Sep - 26 Nov 2025 £985 £280
    1 - 30 Apr 2026 £965 £255
    1 May - 30 Jun 2026 £1050 £290
    21 Aug - 10 Sep 2026 £1015 £285
    11 Sep - 26 Nov 2026 £1045 £295
    3rd & 4th person discount -£155 to -£164
    Single traveller supplement £155 to £165

    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; no dinner is included as the restaurant is closed on Wednesdays.

    Included travel: taxi from Pisa airport to first hotel & rail from Siena to Pisa station

    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.

    4 nights: 01 April 2025 - 30 June 2025, 21 August 2025 - 30 November 2025, 01 April 2026 - 30 June 2026 & 21 August 2026 - 30 November 2026

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

    Starting Price Single room
    1 - 30 Apr 2025 £1210 £240
    1 May - 30 Jun 2025 £1315 £275
    21 Aug - 10 Sep 2025 £1275 £270
    11 Sep - 26 Nov 2025 £1280 £280
    1 - 30 Apr 2026 £1300 £255
    1 May - 30 Jun 2026 £1390 £290
    21 Aug - 10 Sep 2026 £1350 £285
    11 Sep - 26 Nov 2026 £1330 £295
    3rd & 4th person discount -£50 to -£53
    Single traveller supplement £50 to £53

    Includes all elements in the 'walk price', plus standard-class travel by Eurostar from London St Pancras to either Paris, Brussels, Amsterdam, or Lille, with onward travel as described below.

    If you book your holiday less than 6 months in advance of your travel date, seats may no longer be available at the tariffs on which our prices are based, but we may be able to offer you seats on the same services at a supplement.

  • Room upgrades (£ per person per night)

    Hotel Bel Soggiorno, San Gimignano
    Panoramic view: 01 Apr - 30 Jun 2025 £14
    Panoramic view: 21 Aug - 30 Nov 2025 £14
    Panoramic view: 01 Apr - 30 Jun 2026 £15
    Panoramic view: 21 Aug - 30 Nov 2026 £15

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

    Hotel Bel Soggiorno, San Gimignano (B&B) Double room Single room
    01 Apr - 30 Jun 2025 £155 £255
    21 Aug - 30 Nov 2025 £155 £255
    01 Apr - 30 Jun 2026 £164 £270
    21 Aug - 30 Nov 2026 £164 £270
    Deduct £29pp in 2023 or £32pp in 2024 if your stay at Hotel Bel Soggiorno falls on a Wednesday; no dinner is included as the restaurant is closed on Wednesdays.
    Pensione Palazzo Ravizza, Siena (B&B) Double room Single room
    01 Apr - 13 Apr 2025 £93 £166
    14 Apr - 16 Apr 2025 £165 £268
    17 Apr - 30 Apr 2025 £130 £189
    01 May - 30 Jun 2025 £165 £268
    21 Aug - 31 Aug 2025 £130 £189
    01 Sep - 30 Nov 2025 £165 £268
    01 Apr - 13 Apr 2026 £98 £175
    14 Apr - 16 Apr 2026 £174 £283
    17 Apr - 30 Apr 2026 £137 £199
    01 May - 30 Jun 2026 £174 £283
    21 Aug - 31 Aug 2026 £137 £199
    01 Sep - 30 Nov 2026 £174 £283
  • RECOMMENDED AIRPORT(S):
    Pisa
    ALTERNATIVE AIRPORT(S):
    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.

    Travelling from outside the UK
    We have many years' experience catering for customers who live outside the UK, and will be happy to make tailored arrangements to fit with your plans.

    You have two options:

    1) Book your own flights to London, from where we can book flights and onward connecting travel to your hotel.

    2) Book your own flights direct to an airport appropriate to your chosen holiday. You can either make your own way from the airport to the hotel, or we'll be happy to book onward connecting travel for you. Please consult with us before booking your flights, so that we can advise you on the suitability of your proposed route and timings.
    Outward route Airline
    Aberdeen - Florence (via Amsterdam Schiphol) KLM 
    Aberdeen - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Birmingham - Pisa jet2 
    Birmingham - Pisa (via Munich) Lufthansa 
    Outward route Airline
    Bristol - Florence British Airways 
    Bristol - Pisa easyJet 
    Outward route Airline
    Nottingham East Midlands - Pisa Ryanair 
    Outward route Airline
    Edinburgh - Florence British Airways 
    Edinburgh - Pisa Ryanair 
    Outward route Airline
    Glasgow Prestwick - Pisa 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 
    Outward route Airline
    Liverpool - Pisa Ryanair 
    Outward route Airline
    London City - Florence Air France,  British Airways 
    Outward route Airline
    Gatwick - Florence British Airways,  Vueling 
    Gatwick - Pisa British Airways,  easyJet 
    Outward route Airline
    Heathrow - Florence British Airways 
    Heathrow - Pisa British Airways 
    Outward route Airline
    Luton - Florence Vueling 
    Luton - Pisa easyJet 
    Outward route Airline
    Stansted - Pisa Ryanair 
    Outward route Airline
    Manchester - Florence British Airways 
    Manchester - Pisa easyJet,  jet2,  Ryanair 
    Outward route Airline
    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 Pisa

    Outward route Price per person Latest flight
    arrival time
    direct taxi Pisa airport to hotel (1h15) included flexible
    Homeward route Price per person Earliest flight
    departure time
    taxi hotel to Siena station (0h05, pay locally), rail Siena to Pisa Centrale (2h15) some elements included 1200
 
Reviews

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 >

All 5 reviews
  • Mr P Davis
    Petersfield
    19 May 2024

    The area was superb and the walks were exceptionally good.

  • Mrs M Franklin
    Chislehurst
    21 October 2023

    Excellent organisation of trip, walking notes very clear. Transfer of luggage efficient. Quality of 2 of 3 hotels excellent. Overall very good trip. I would recommend the company. 

  • Mr M Pinhorn
    Emsworth
    15 September 2023

    Although, we had to pay extra for Palazzo Ravizza delxe room (I believe you could not fit us in your first choice), we both thought it an excellent venue, with that 'WOW' factor. The Pensione did actually provide breakfast for the guests as a 'compliment'. That said, the other hotels were first class.

    Travellers should be mindful when in this area of the lack of taxis. We asked the hotel in Siena to order a taxi to take us to the train station and in Bologna to take us to the airport, in plenty of time. But on both occasions we only just made it. In Siena we had to run for the train, as it was about to depart! Apparently, this is due the enormous numbers of tourists swamping local taxis firms and travel companies pre-booking slots for their clients.

  • Mr I Taylor
    21 May 2023

    The view and breakfast at Hotel Bel Soggiorno was just amazing. San Gimignano and the views of it looking back on the first day of hiking were the highlight. Another highlight was the stop at Marcello Pagnini's on the second day of hiking. Also the meal at Portonovo Restaurant (as part of the stay at Palazzo San Lorenzo) - authentic Tuscan food, beautiful flavours.

  • Mr B Marshall
    Witney
    21 April 2023

    San Gimignano to Colle di Val d'Elsa fantastic. Hotels disappointing. Don't do the walk to Siena - look elsewhere.
 

FAQs

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.
  • 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 >
  • 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 www.gov.uk/visit-eu-switzerland-norway-iceland-liechtenstein.
  • 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.
Price from
£955pp | 4 nights
Hill-Top Towns of Tuscany with San Gimignano - Short Break. 4 nights
Price from
£955pp
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