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.


We are currently unable to take bookings for this holiday for 2024. There are, however, many other holidays to choose from, so why not browse our site some more?


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 Hotel La Vecchia Cartiera or Il 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: 30km; longer option: 38km
    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: 30km
    Circular route from Colle Val d’Elsa (longer option): 38km
  • Colle Val d’Elsa to Toiano: 34km
    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: 34km
    Pause for lunch
  • 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: 36km, ascent 550m/descent 575m
    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: 36km
    En route from Siena to Pieve a Salti
  • Choice of routes from Pieve a Salti: 26km to 36km

    Out-and-back route to Montalcino: 36km
    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: 26km
    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: 36km
    Out-and-back route to Casato Prime Donne: 26km
    Circular route via Monte Oliveto: 30km


You stay in a delightful mix of accommodation.

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.

Options to extend or shorten your stay

What is included
  • 7 nights
  • 2 dinners
    7 breakfasts
  • luggage transported
  • high-quality bicycle
  • route notes and maps
  • GPS navigation

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.
  • 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, which remain the principal means of navigation).
  • 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.

    For more detailed information, see our cycling holidays in Europe page.
  • You are responsible for damage to or loss of the rental bike while it is hired to you. Always be careful to lock it up, ideally to an immovable object, and remove all easy-to-steal accessories whenever you leave it unattended.
  • 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 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.
Last fetch time is : 12/5/2023 6:59:40 PM

currency iplookup:

cookie value: null

querystring value: null