Road Cycling in Tuscany

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Take on the rolling Tuscan hills and visit facinating towns like Volterra, Siena & Florence 

Rolling hills as far as the eye can see, meandering roads lined with Cyprus trees and ancient hilltop towns waiting to be explored, Tuscany is everything you would imagine it to be! On this tour we discover some of the best cycling roads Italy has to offer, following segments that have been made famous by the Giro d’Italia and Strada Bianche bike races. We take on spectacular climbs and twisting descents as we pedal through the Chianti region to popular towns like Siena and Volterra. As well as the famous sights and incredible cycling, this tour allows us to indulge in some truly delicious local produce from the traditional Picci pasta in San Quirico, to the wild boar of Chianti and the abundance of great wines like Brunello di Montalcino and Vino Nobile di Montepulciano. 


  • Cycle roads from the beautiful Strada Bianche bicycle race 
  • Explore the magnificent Tuscan countryside 
  • Discover Siena, Volterra and Florence

Key information

  • 7 nights in 3 and 4 star hotels with en suite facilities
  • 6 days cycling, average 80km per day
  • Partial vehicle support (with limited seats)
  • 100% tarmac roads over a hilly route with some long climbs 
  • All breakfasts included 


What's included

  • All breakfasts
  • All accommodation (see below)
  • All transport and listed activities 
  • Tour leader throughout
  • Flights from London (if booking incl. flights)

What's not included

  • Travel insurance
  • Local bike hire (available on request)
  • Single accommodation (available on request)
  • Visas or vaccinations
Call for general departures:
020 8772 3936
Call for tailormade trips:
+44 (0)20 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.


Days of Cycling

Approximately 4-6 hours cycling per day


100% tarmac roads with an average of three longer climbs per day 

Day by day breakdown
Day 285.0km/53.0miles
Day 3105.0km/65.0miles
Day 451.0km/32.0miles
Day 570.0km/43.0miles
Day 6130.0km/81.0miles
Day 765.0km/40.0miles

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Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here… 


  • Day 1

    Start San Quirico d'Orcia

    Start San Quirico d'Orcia; upon arival there will be time to set up bikes before going out for a group meal and tour briefing.

  • Day 2

    Circular ride through the rolling Tuscan hills; taking in the climbs to Montepulciano and Campiglia d’Orcia.

    After breakfast we get on the bikes and head out through undulating rolling hills via Pienza to the picturesque hilltop town of Montepulciano (662m) where we can stop for a coffee. From here there is a fast descent to Castelvecchio where we start the most challenging climb of the day up to Campiglia d’Orcia (780m), this climbs is about 7km long with a total ascent of 450m and some sections above 14%. After a stop at the top to re-group and take pictures the ride continues back to our accommodation in San Quirico d’Orcia. 

    Meals included: Breakfast
  • Day 3

    Ride to Siena; ending with an ascent up to the Piazza del Campo as seen in the Strada Bianche bike race.

    Leaving the hotel we head east and start the first challenge of the day as we climb to the hilltop town of Montalcino (620m) where we can stop for a coffee and a quick pedal around the pretty old town. From here we have a fantastic 12km descent and a rare section of flatter roads before stopping for lunch in Monte Antico. After lunch we head back into the hills and cycle onto Siena, our overnight destination. Depending on arrival time we will do a short orientation ride around the city before dinner. 

    Meals included: Breakfast
  • Day 4

    Siena café ride; a short loop to Lecci and back.

    Today we have a shorter ride into the hills surrounding Siena. We start by heading north out of Siena and gradually climb to the town of Lecchi, here we will stop for a coffee and snack break before getting back on the bikes to complete the loop via La Madonna and Pianella back to Siena. There will be some free time to relax in Siena or explore the fascinating old town. 

    Meals included: Breakfast
  • Day 5

    Point to point ride from Siena to Castellina in Chianti.

    After breakfast we leave Siena in a similar direction to yesterday but carry on riding much further north all the way into the heart of the Chianti region. We will cycle through Gaiole in Chianti which is famous for being the start town of the well known L’Eroica sportive, then continue to the pretty town of Radda in Chianti where we can visit one of the best bike shops in Italy before ending our ride in Castellina in Chianti. Our hotel here has a swimming pool and large garden area to relax in with a beer after today’s ride.

    Meals included: Breakfast
  • Day 6

    Loop ride to the hilltop town of Volterra via San Gimignano.

    Today is the toughest day of the tour so a big breakfast is recommended! We start with a long descent down to Colle di Val d’Elsa before climbing to the hill top town of San Gimignano where we can eat what is meant to be the best gelato in Italy. From here we have several climbs including the biggest ascent of the day up to Volterra (550m), we will stop for lunch here and have a short ride around the fascinating ancient town before riding a slightly shorter route back to Castellina in Chianti. 

    Meals included: Breakfast
  • Day 7

    Cycle to Florence through the foothills of Monte Castellino.

    For the final stage of our tour we take on some stunning climbs and descents as we make our way to Florence, the capital of the Tuscany region. We start off with an 8km descent before taking on the ascent to Panzano (520m) and Sugame (570m), from here our ride is mainly downhill before finishing on a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo for a final group shot. We will arrive in Florence in the early afternoon, giving you time to start exploring this wonderful city of the Renaissance including the Cathedral and Baptistry – the oldest building in the city. Also see the Ponte Vecchio, the superb bridge over the river Arno, lined with goldsmiths and the most famous symbol of the City.

    Meals included: Breakfast
  • Day 8

    End Florence.

    After breakfast the tour ends in Florence.

    Meals included: Breakfast
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Essential Info



No visa required for British passport holders.
Please note in Italy it is compulsory to carry ID with you at all times.



There are no specific health risks.

Eating and Drinking

All breakfasts are included and are continental style; consisting of a selection of cold meats, cheeses and eggs, pastries, bread and jams, as well as tea and coffee.

Italy’s cuisine is hearty, satisfying and full of flavour. Inspired by the kitchens of the nonna, Italy’s food is authentic and surprising – pizza and pasta are only the tip of the iceberg when it comes to the diverse array of unforgettable food you’ll find on this trip.

Starters include antipasti of cured meats or a crustini di fegato made from toasted slices of bread with a chicken liver pate.

Soups options are the zuppa di fagioli, with beans, or ribollita, a deliciously hearty vegetable and bread soup. The tagliatelle al tartufo brings the delicious flavors of truffles into a rich, luscious pasta dish whether the bistecca florentina, a mouth-watering t-bone steak takes centre stage for main course.
End your meal with cantucci biscuits, dipped into a glass of vin santo, sweet dessert wine for a true taste of Tuscany.

Vegetarians are well catered for in Italy. Please inform us of any dietary requirements at the time of booking.


Italy has a good all year round climate, with plenty of sunshine and warm temperatures from the spring through to autumn. Summer departures will usually have hot weather, with temperatures reaching the low to mid 30s. April-June and September-November departures are likely to be cooler with a slightly higher chance of rain. In late summer there is the possibility of heavy thunderstorms (generally in the afternoons), but these are usually short-lived.

Is this trip for you?

This tour is classified: Drop Bars

Activity level: 7 (Tough)

6 days cycling with an average daily distance of 80km per day and partial vehicle support (with limited seats). 100% tarmac roads

Tuscany is an area known for its rolling hills and on this tour we take on quite a few, though the climbs don’t go much over 10% they can be long (up to 10km) so a good level of fitness is required for this holiday. Cycling days will be broken up with coffee, lunch and gelato stops so the complete daily distances will not be ridden in one go. A support vehicle will be following the group at all times and will be on hand to carry any essential items you might need for the day as well as food, drinks and spare items of clothing. A cycling guide accompanies the group at all times on this tour. 

Call for general departures:
020 8772 3936
Call for tailormade trips:
+44 (0)20 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.


Road Cycling in Tuscany

You will spend 7 nights in family run and comfortable 3-4 star hotels. All accommodation have been carefully selected for their welcoming atmosphere and all rooms have en suite facilities. Some hotels have a swimming pool where we can relax after the long cycling days.

We can arrange single rooms throughout the trip (subject to availability). Please check with your sales consultant for availability and prices.

Call for general departures:
020 8772 3936
Call for tailormade trips:
+44 (0)20 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Expert Blog Entries

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  • Reviewed August 2018
    shirley Oliver

    Beautiful landscape

    Stunning landscape and beautiful towns and cities. The group were diverse and the tour leaders were amazing; professional, understanding and very knowledgable. I could only go in July/August due to school breaks and the weather was very hot but it was throughout Europe. The course was 'moderate' and I'm glad I had had some hill practise before. Lovely group of people and I would recommend this for trip for single or couple travellers. The wine was very good too!

    What was the most inspirational moment of your trip?

    Siena was really stunning.

    What did you think of your group leader?

    Both Jon and Martino were exceptionally helpful, patient and competent. They were flexiable and could easily recommend things to do, see and visit.

    Do you have any advice for potential travellers?

    You would need a certain fitness level - not too high, but the heat/hill combination was often in contrast to cycling in the UK.

    Is there anything else you would like to add?

    I would go again - for the company, scenery, cycling, food, wines and gelato.

Dates & Prices

An overview of flight options

Exodus is committed to making joining our tours as easy as possible, wherever you live. We generally only block book seats from London, but this certainly does not mean that you need to fly from there. Depending on the route and airlines available, there will usually be various options available for those who want to fly from their local airport.

This page aims to provide a useful overview of the options available to our clients. However, the best flight arrangements should be tailored to your personal requirements, so please contact our Sales team for expert advice.


What kind of options do I have ?

1. We can book for you: Flights from anywhere in the world - not via London  

Depending on the route, this may be direct or via an overseas hub like Amsterdam, the Middle East or elsewhere. On short haul routes there may be direct flights with low cost airlines, charter flights or scheduled airlines. Exodus can book most, but not all, of these for you. The most appropriate airline may be different to that which we use for the group flight from London, but many people now travel on different airlines and meet up with their fellow passengers at the destination.

Pros Cons
  • May be the most direct route
  • Often the extra fare compared to the London flight is minimal.
  • As you will be in the hands a single airline for your entire journey, the airline will be responsible for your bags and your connections.
  • You may not be able to join the group transfers. However, we can usually arrange private transfers, or book your flights to try and coincide with the group transfers. See notes on transfer arrangements below.


2. We can book for you: Connecting flights from your local airport to London

Exodus can book connecting flights to London so you can join the group flight there. Connecting times will be followed according to airline advice, or as requested by clients. There are two types of fares we can use for this option: a 'through-fare' or a 'published fare'.
a) A 'through-fare' is where you will be in the main airline's care throughout. You change planes, but your bags are checked all the way through to your final destination. 

b) A 'published fare' ticket is completely seperate from your onward ticket from London. It is usually cheaper than a through-fare but will need to be paid for and issued as soon as it is booked. This can be a problem if your tour has not yet reached minimum numbers. On 'published fares' neither airline is aware that you have connecting flights, so Exodus is responsible for timing your connection, not the airlines involved. The tickets are also usually non changeable and non refundable.

Pros Cons
  • Depending on the fare type, Exodus or the airline is responsible for flight connections.
  • Through fare tickets can be expensive.
  • On a published fare, tickets must be issued immediately; tickets on published fares can be very difficult to change if onward flight times change; bags are not checked though to your final destination.
  • Published fares are non-refundable.


3. Booking some or all of the flights yourself

You can also book connecting air travel yourself, either to London, or all the way to the start point. There may be certain airlines or routes we don't have access to, so this is always an option. However, if you make your own travel arrangements you become liable for any delays, cancellations or missed connections, and Exodus is not required to offer refunds if you have trouble reaching the start of your trip.

Pros Cons
  • You might find cheaper fares, or routes not available to Exodus.
  • You are responsible for any delays or missed connections, and the cost of the tour is not protected should you miss your flight be cancelled.


 Notes on transfer arrangements

Sometimes it is possible to travel on a different airline to the group flight from London. Where this is the case, we need to think about ensuring you meet up with the group with minimum extra cost and hassle.

  • On certain trips, it is easy to arrive on a different flight and still meet the group at the hotel with time in hand. We can usually arrange private transfers (at extra cost) or offer advice on taking a taxi to the start hotel.
  • On other trips (especially in Europe), the transfer meets the group flight and then travels some distance to the first night's accommodation. Where this is the case, our Sales team will try to arrange flights that arrive before (and depart after) the group. However, we do have to make it clear in your final documentation that if your flights are delayed, the transfer cannot wait for you. While Exodus or our local operators will do what we can to help you reach the start point of the tour, any additional costs must be paid by the client. 


Next steps? 

Call our Sales team on: 0203 733 0698

Email your query: [email protected]

Call us on 020 8772 3936