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Tuscany on Two Wheels

Towers, cypress trees & Chianti
Experience classic, rolling Tuscan landscapes as you cycle self-guided between quality accommodation, while your luggage is transported. Savour the famously delicious food and wine, and visit unforgettable San Gimignano with its medieval towers, and UNESCO-protected Siena.
Tuscany on Two Wheels. 7 nights
Tuscany on Two Wheels. 7 nights

Holiday information


A cycling holiday in Tuscany

Admire the celebrated towers of San Gimignano and savour the winning combination of Tuscan regional cooking, with its renowned meat and pasta dishes, and world-class wines such as Chianti and Brunello, on a memorable cycling holiday that includes magnificent Siena.
The Chianti Hills are as famed for their beauty as for their dark red wines. Hill-top villages crown the rolling landscapes, and every church seems to contain a fine painting.
As you cycle, you will be struck by an extraordinary sense of history, from the towers of San Gimignano to Siena’s magnificent Campo, and the alluring timelessness of the countryside in between.


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 Colle Val d’Elsa
    Night 1: at Relais della Rovere (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 cycling.
  • Circular route from Colle Val d’Elsa: 32km; longer option: 40km
    Winding roads with some short ascents followed by a longer but steady climb lead you towards San Gimignano. Perhaps the best-known village in all of Italy, it provides an unmistakably dramatic skyline as you approach, with its 14 medieval towers piercing the sky. The town is immaculately preserved and boasts a fine array of museums and galleries. Admire the panoramas in all directions before returning to Colle Val d’Elsa, either along a low ridge to the east of San Gimignano which offers a different perspective of its skyline or along a longer, more demanding route through beautiful countryside.
    San Gimignano
    Circular route from Colle Val d’Elsa: 32km
    Circular route from Colle Val d’Elsa (longer option): 40km
  • Colle Val d’Elsa to Toiano: 35km
    Today’s route passes from the Elsa Valley into one of Tuscany’s least-known areas, the Merse Valley, crossing wide-open spaces and the ancient wooded hills of Montagnola. There are plenty of small villages and hamlets to discover along the way, such as Scorgiano – where it is possible to pre-arrange wine-tasting from a small local producer – and Pievescola. After a long but gradual ascent to another village, the day ends with a descent onto the plain to reach your hotel, the Relais Borgo di Toiano, near Sovicille, where you spend two nights.
    Colle Val d’Elsa to Toiano: 35km
  • Circular route from Toiano: 23km
    If you can tear yourself away from the hotel pool, we suggest a gentle ride through a section of La Montagnola, mostly following winding traffic-free roads through silent woodland. It is worth pausing at the beautiful Augustinian hermitage of San Leonardo, before you return via 16th-century Villa Cetinale and its spectacular gardens.
    Circular route from Toiano: 23km
  • Toiano to Siena: 34km
    Discover changing scenery dotted with small yet captivating medieval hamlets as you leave the Merse Valley behind. The panoramic roads afford idyllic Tuscan views as you approach the Gothic cityscape of Siena, where you stay at the Hotel Santa Caterina, a charming hotel to the south of the city centre.
    Toiano to Siena: 34km
    Magnificent medieval architecture awaits in Siena
  • Siena to Pieve a Salti: 35km
    Leaving Siena, the route heads south into the Crete Senesi, where you are greeted by a completely different landscape – beautiful rolling farmland, hill-top fortresses and remote hamlets provide a scenic backdrop as you pedal along quiet country roads and strade bianche. As you near the end of today's ride, the road swoops steadily down into Buonconvento, from where a short but steep climb leads up to Pieve a Salti, your destination for the final two nights.
    Siena to Pieve a Salti: 35km
    En route from Siena to Pieve a Salti
  • Choice of routes from Pieve a Salti: 22km to 33km

    Out-and-back route to Montalcino: 33km
    This route heads to the wine-producing village of Montalcino, famed for its Brunello di Montalcino reds. It starts by taking you back to the historic town of Buonconvento, beyond which the landscape opens up, offering views towards Montalcino, with the volcano of Mount Amiata silhouetted behind. As you near Montalcino, the farmland and fields of sunflowers give way to olive groves and vineyards. You rise steeply into Montalcino, where it is worth spending some time exploring the ancient streets and visiting the pentagonal fortress before returning to Pieve a Salti along the same route.

    Out-and-back route to Casato Prime Donne: 22km
    For a shorter day through similar scenery, you could instead ride to a vineyard for a spot of wine-tasting, a very apt way to spend your final day in Tuscany.

    Circular route via Monte Oliveto: 30km
    Another alternative route leads you through the evocative scenery of the Crete Senesi to Monte Oliveto and its huge frescoed monastery.

    Explore Montalcino
    A final option could be to explore Montalcino on foot, catching the local bus from nearby Buonconvento.
    Out-and-back route to Montalcino: 33km
    Out-and-back route to Casato Prime Donne: 22km
    Circular route via Monte Oliveto: 30km


You stay in a delightful mix of accommodation.

Options to extend or shorten your stay


Prices for 2020

We are in the process of updating our prices for 2020. If you’d like to book now, please contact us – we’ll be happy to provide a quotation.
Get in touch >
Prices & travel options
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  • 7 nights: 15 April 2019 - 30 June 2019 & 25 August 2019 - 31 October 2019

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

    Starting Price Single room
    15 Apr - 23 May 2019 £995 £250
    24 May - 23 Jun 2019 £1045 £260
    25 Aug - 22 Sep 2019 £1085 £335
    23 Sep - 5 Oct 2019 £1045 £260
    6 - 9 Oct 2019 £995 £250
    10 - 24 Oct 2019 £975 £240
    3rd & 4th person discount -£105
    Single traveller supplement £105

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

    Electric bikes available: add £110 per person

    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 della Rovere, Colle Val d'Elsa
    Junior suite: 15 Apr - 17 Apr 2019 £24
    Junior suite: 18 Apr - 21 Apr 2019 £30
    Junior suite: 22 Apr - 27 Jun 2019 £24
    Junior suite: 28 Jun - 30 Jun 2019 £30
    Junior suite: 25 Aug - 22 Sep 2019 £30
    Junior suite: 23 Sep - 31 Oct 2019 £24

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

    Prices include an extra day’s hire of a standard bike. If you are upgrading to an e-bike, add a further £25pp per day.
    Relais Borgo di Toiano, Toiano (B&B) Double room Single room
    17 Apr - 31 May 2019 £75 £100
    01 Jun - 30 Jun 2019 £85 £120
    25 Aug - 10 Oct 2019 £85 £120
    11 Oct - 31 Oct 2019 £75 £100
    Hotel Santa Caterina, Siena (B&B) Double room Single room
    15 Apr - 18 Apr 2019 £60 £72
    19 Apr - 21 Apr 2019 £124 £164
    22 Apr - 30 Apr 2019 £110 £135
    01 May - 31 May 2019 £124 £164
    01 Jun - 29 Jun 2019 £110 £135
    30 Jun - 30 Jun 2019 £124 £164
    25 Aug - 31 Aug 2019 £110 £135
    01 Sep - 13 Oct 2019 £124 £164
    14 Oct - 31 Oct 2019 £110 £135
    Fattoria Pieve a Salti, Pieve a Salti (with dinner) Double room Single room
    15 Apr - 30 Jun 2019 £100 £130
    25 Aug - 06 Sep 2019 £108 £140
    07 Sep - 31 Oct 2019 £100 £130

    Travelling from the UK

    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Rome or Milan.  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 
    Outward route Airline
    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 - 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
    Gatwick - Pisa British Airways,  easyJet 
    Outward route Airline
    Heathrow - Pisa British Airways 
    Outward route Airline
    Luton - Pisa easyJet 
    Outward route Airline
    Stansted - Pisa Ryanair 
    Outward route Airline
    Manchester - Pisa easyJet,  jet2 
    Outward route Airline
    Newcastle - Pisa jet2 
    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Rome or Milan.  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 £30 per person for our flight booking service (£50 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 Poggibonsi (1h20), taxi from station to hotel (0h10) £24 1700
    Homeward route Price per person Earliest flight
    departure time
    hotel transfer to Buonconvento (0h10), rail Buonconvento to Pisa Centrale (2h30) £21 1300
What is included
  • 7 nights
  • 2 dinners
    7 breakfasts
  • luggage transported
  • route notes and maps
  • high-quality bicycle

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.
  • Our cycle supplier will provide you with a touring bike with 21 gears; a waterproof map case on handlebars; panniers/saddlebags; pump; puncture repair kit; and a lock. Electric bikes are available as an upgrade (see price panel), subject to availability, and must be requested at the time of booking.
  • While we would always recommend that you take your own well-fitting helmet, they can be hired locally for a small fee. Please let us know at the time of booking if you would like to hire a helmet.
  • Yes, we will provide GPX tracks for this holiday prior to departure so that you can follow your route on your smartphone or dedicated GPS device if you wish. (We also provide maps and our tried-and-tested route notes.)
  • 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. On mornings 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 so that all you need to take with you are a camera, sun cream, drinks, food and waterproofs.
  • You do need to make sure you’re covered, because it’s you who is responsible for any damage to or loss of the bike during the holiday. You should always lock it (preferably to an immovable object) and remove any easy-to-steal accessories when leaving it unattended. The travel insurance policy that we offer covers you for loss and damage (provided you’ve locked or stored it appropriately). If you are arranging your own insurance, but it doesn’t cover bikes, we can provide bike-only cover for £19 per person. More details >
  • 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 £30 booking fee per person (£15 for children aged 2-11). For India and Nepal, the booking fee is £50 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 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.
  • 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 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.
  • 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 travelling after 31 October 2019, see the Brexit question below for more information). 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 can be found through the following NHS link: 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. EHICs may cease to be valid in the event of a no-deal Brexit.
  • 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.
  • Even in the event of a no-deal Brexit, it’s been confirmed that flights will continue as normal and that you won’t need a visa to go on holiday (the limit on stays is 90 days). What you will need if there’s no deal is a passport that is valid for at least 6 months beyond the date of your arrival (extra months added because you renewed your passport early do not count) and adequate travel insurance to cover you for accidents and illness in case reciprocal health deals are suspended. If you are driving while on holiday, you will probably need an International Driving Permit (plus a Green Card if you are taking your own car to Europe). More information >
  • 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.
Last fetch time is : 10/22/2019 10:05:59 AM