Tuscany Cycle Siena & Chianti

Tuscany Cycle Siena & Chianti

8 Days From



Tuscany Cycle Siena & Chianti

8 Days Starting in San Quirico and ending in Florence

Visiting: San Quirico, Montepulciano, Pienza, Bagno Vignoni, Province of Siena, Chianti, San Gimignano, Monteriggioni, Florence, Greve in Chianti

Tour operator:


Tour code:


Guide Type:

Fully Guided

Group size:

6 - 16

Physical rating:


Age range:


Special diets catered:

Vegetarians, Vegans, Please inform Exodus of specific dietary requirements

Tour operated in:
Trip Styles:

Adventure Tours


Cycling, Sightseeing, Walking

$2845 Operator discount: -$148 Exclusive Tourhub Discount: -$80

NB: Prices correct on 20-May-2024 but subject to change.

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Tour Overview

The Tuscan landscape is one of the most evocative and romantic in Europe with cypress trees lining the roads, olive groves, vineyards, ancient hill-top towns and, of course, classic Renaissance cities. Our group cycling tour is carefully planned to take in the best of Tuscany without feeling rushed: part of the joy of the Italian lifestyle is sitting and watching the world go by with a glass of wine in your hand! During the week we ride through diverse areas of Tuscany, such as the hills of Chianti and the beautiful countryside around Montepulciano. Riding north, we enter 'Le Crete', a wonderfully scenic region that's home to some of Tuscany's best towns and villages. We then enjoy Siena's magnificent Campo before biking past the towers of San Gimignano and onto our final destination in Florence. Following country roads wherever possible, we mix point-to-point and circular rides to make a perfect cycle tour of this region.


  • Visit some of Tuscany's most beautiful hilltop towns

  • Accessible by train. Read more here.

  • Enjoy famous Tuscan cuisine and wine

  • Explore the cultural cities of Siena and Florence

  • Explore the cultural cities of Siena and Florence

  • Ride along the scenic country roads of classic Tuscany


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Day 1 : Start San Quirico.

Location: San Quirico

Meals Included: No Meals

Start in the hilltop town of San Quirico D'Orcia, one of the most beautiful

and charming medieval towns of the Orcia Valley.


Day 2 : Circular Ride Through Classic Tuscan Countryside Via Pienza, The Wine Town Of Montepulciano And Thermal Spa Village Of Bagno Vignoni.

Location: Montepulciano, Pienza, Bagno Vignoni

Meals Included: Breakfast

Today we head towards Pienza, a charming town full of history and culture.

From here we cycle to the beautifully situated wine centre of Montepulciano,

famous for its Vino Nobile. We then head towards the mediaeval village of

Monticchiello and on to the well known thermal bath of Bagno Vignoni, before

making our way back to the hotel.

Day 3 : Ride Through Vineyards And The Walled Town Of Murlo To Siena.

Location: Province of Siena, Province of Siena

Meals Included: Breakfast

A classic day's riding, showing Tuscany at its most picturesque. Following

back roads, we head out of San Quirico with a first stop at Montalcino. We

then descend on the road to Buonconvento and ride back up to Murlo passing

by Bibbiano. From here we ascend the short but steep Rospatoio Pass and take

a lovely road section via Ville di Corsano, as we approach the splendid

gothic city of Siena.

Day 4 : Free Day In Siena To Explore Or Relax.

Location: Province of Siena

Meals Included: Breakfast

Siena is one of Italy's best-preserved medieval towns with one of the world's

most gracious squares, the Campo. There is plenty to see in Siena and its

sights are best explored on foot as the town is compact but hilly. There are

many museums and buildings of interest to visit, such as the impressive

Duomo. Alternatively you may choose to head out for an unguided ride. On the

June 30th departure you will get the chance to be in Siena during the 'Palio

Horse Race', one of Italy's most famous annual sporting events and experience

the thrilling atmosphere around it. Held in honour of the Virgin Mary, ten

of the city’s seventeen contrade, or districts, are represented by a horse

and jockey in each race and will compete against each other during this

event. It has been held in Siena’s civic hub, Piazza del Campo, since 1644

and local people get involved to a level that it is still common for

‘mixed-marriage’ couples to separate for the days leading up to and

including the race if the contrada of the husband and wife both have a horse

in contention.

Day 5 : Ride Via Gaiole And Radda To Castellina In Chianti.

Location: Chianti, Chianti

Meals Included: Breakfast

From Siena we head directly into the heart of Chianti. Our picturesque route

takes us via some lovely small villages and hamlets, as well as some

spectacular vineyards and castles, such as that of Castello di Brolio. Here

there is the option to taste some of the area's finest wines. We then cycle

on to Gaiole for lunch and after a gelato stop in Radda, we follow our final

section to Castellina in Chianti, where we stay for two nights.

Day 6 : Circular Ride Through The Chianti Hills Via Towers Of San Gimignano And Monteriggioni.

Location: San Gimignano, Monteriggioni, Monteriggioni

Meals Included: Breakfast

From Castellina, we ride through rolling countryside before taking an

amazingly scenic descent into the lower valley. From Poggibonsi we head

towards the distant towers of San Gimignano, nestled between the hills and

small hamlets. The Unesco town is one of the most visited and interesting

sights in Tuscany; famous for its towers, Vernaccia wine & Safron. We spend

a few hours enjoying the atmosphere, walking by the walls and admiring the

town's high towers. Our return route involves a long but beautiful climb

before reaching Castellina and enjoying a well deserved gelato. 

Day 7 : Cycle To Florence Via Panzano And Greve In Chianti.

Location: Florence, Greve in Chianti

Meals Included: Breakfast

Our final spectacular ride passes through Panzano in Chianti towards the

market town of Greve in Chianti. This is described as one of the most scenic

roads which links Florence with Siena through the Chianti hills. Here we have

time to admire the triangular piazza which hosts the famous Chianti wine

festival before heading towards Strada and Impruneta, known for their local

terracotta production. In Impruneta we stop for our lunch. We finish by

taking 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.

Day 8 : End Florence.

Location: Florence

Meals Included: Breakfast

End in Florence. Please speak to our sales team if you would like to book

extra nights in this magnificent city.


What's Included

  • Meals
    7 breakfasts, 0 lunches, 0 dinners.

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

What's Not Included

  • Travel insurance

  • /Local taxes (approx. EUR 20 per person, see Trip Notes)/

  • Visas or vaccinations

  • Single accommodation (available on request)


All breakfasts are included and are Continental in style, consisting of
coffee or tea, cereals, cheese and cold meat, bread, pastries, yoghurt, jam
and/or honey.

Italy’s cuisine is hearty, satisfying and full of flavour. Inspired by the
kitchens of the nonna, Tuscany’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.


You will spend seven nights in family-run and comfortable three-star hotels. All accommodations 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.

Examples of hotels used are:

Orcia Valley: Hotel Palazzuolo, Residence Casanova or Il Chiostro di Pienza

Siena: Hotel Minerva

Castellina in Chianti: Hotel Il Colombaio or Hotel Casafrassi

Florence: Hotel Classic

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

Check out our Q&As

  • Who is Exodus Travels?

    At Exodus Travels, we've been exploring the world for nearly 50 years. From Walking and Trekking, Cultural and Cycling, Responsible Wildlife, to Polar and our new Premium Adventures, we are proud to offer award-winning small group and self-guided tours to 100+ countries worldwide.

  • Are children permitted to take part in the tour?

    The minimum age for this tour is 16 years old.

  • Can you assist with pre or post tour accommodation?

    We are happy to assist with pre and post tour accommodation. Please enquire for detailed information.

  • Is there a supplement for solo travellers?

    If you would like to be paired with a tour member of the same gender, there is no additional charge. A single supplement can be requested if you would like your own room.

  • Are the local guides on the tour English speaking?

    Yes, our local guides are English speaking.

  • Are flights included in this tour?

    International flights are not included with this tour.

  • What happens if I need to change my holiday date once I’ve booked?

    If you wish to make any changes to your booking, particularly if you need to alter any flights booked through us, please let us know as soon as possible. There is a booking or flight amendment fee of £40 per change and flight amendments often incur extra airline costs depending on the changes to be made and if the ticket has been issued or not.

  • How long has the tour company been trading?

    Exodus has been trading since 1974

  • What documents will I receive before I travel?

    Your final joining instructions and flight details, if booked with us, will then be sent out 2 to 3 weeks before departure. If you would like a hard copy posted, or if you require these any earlier, please contact the customer operations team. We advise that if you are booking connecting travel before receiving these, please ensure you leave plenty of time.

  • Do you operate a “single share” option and how does it work?

    Travellers are welcome to opt to share a room with a tour member of the same gender for no additional charge. If you'd like your own room, we can request a single supplement so that you will have your own room throughout.

  • Can I join the tour once it has departed?

    You are welcome to meet the group after the tour has departed however there is no reduction in rate for joining a tour after the departure date.

Reviews from travellers on this tour

Tuscany cycle - Siena & Chianti

A fantastic trip - awe inspiring scenery, pictures

A fantastic trip - awe inspiring scenery, picturesque hill towns, wonderful historic cities, excellent guide & support & great cycling! What more could you wish for? Oh yes, good food & great company. This trip had it all.

Cycling Siena and Chianti

Great cycle routes, well planned stops, good climb

Great cycle routes, well planned stops, good climbs and descents.


Not what was expected but thoroughly enjoyable.

Not what was expected but thoroughly enjoyable.

Fantastic cycling in stunning Tuscany

A well organised wonderful cycling tour with a per

A well organised wonderful cycling tour with a perfect balance of cappuccino/gelato and lunch breaks, often in charming ancient hill towns where there was always time for a bit of exploring too. I've fallen in love with Tuscany and Chianti, the scenery is simply stunning, the route was fantastic with a great mix of some challenging hills, fabulous descents.... and even some flat bits too amidst the rolling hills! Nice small group and decent hotels too!

Beautiful at every turn

An incredible week of superb food, hill top towns,

An incredible week of superb food, hill top towns, challenging cycling, new friends of all abilities and a well structured itinerary!

Cycle Tuscany and Chianti

A spectacular cycling trip with a 'wow' at every t

A spectacular cycling trip with a 'wow' at every turn and summit. It blends fantastic scenery with exactly the right amount of culture which a cycling holiday in this region rightly deserves. The food and wine are likewise to the exquisite standard you would expect;so don't go in the hope of loosing weight.

Great trip, difficulty rating a bit misleading

Our second trip with Exodus. A really good group

Our second trip with Exodus. A really good group of cyclists to ride and socialize with. Leaders Becs and David did a great job supporting us and handling both the expected and the unexpected. The scenery was spectacular. Having been on another level 3 tour, I would suggest that this one was significantly more difficult. I think Exodus needs to make some changes in the difficulty ranking system. I would be skeptical about the ranking and would want to talk to someone who had been on the trip I was considering. That said, we would do it again!

Tuscany May 2015

This is our second Exodus bike trip - we will defi

This is our second Exodus bike trip - we will definitely keep coming back. The Tuscany region is exactly like you would see in the photos, rolling (undulating) hills, vineyards, and wonderful historic cities. We appreciated the stops to see the towns and scenery and of course enjoy a well deserved gelato. The food and wine was more delicious than we could ever have imagined. Our guides Radu and Liz were able to give great tips on where to go and what to see. You can never totally plan on the weather cooperating - the rain and cold on the last day to Florence were a bit much but it certainly didn't ruin what was a perfect trip.

Susan, Christchurch

A wonderful tour of a beautiful region, using quie

A wonderful tour of a beautiful region, using quiet roads and enjoying authentic Italian cuisine


This trip was a great balance of exercise, culture

This trip was a great balance of exercise, culture and all round fun. The accommodation was very good too. No surprise to learn there were lots of hills, but the pacing was good for the slower ones like me, and the support was excellent. 

Read all 43 reviews

1 Dates & Availability

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Saturday - Saturday

Sep 07, 2024 - Sep 14, 2024
$3073 $2845

Operator discount: -$148

Exclusive Tourhub Discount: -$80

Instant Booking Available

Saturday - Saturday

Sep 28, 2024 - Oct 05, 2024
$3073 $2845

Operator discount: -$148

Exclusive Tourhub Discount: -$80

Instant Booking Available

Saturday - Saturday

Oct 05, 2024 - Oct 12, 2024
$3073 $2845

Operator discount: -$148

Exclusive Tourhub Discount: -$80

Book with Confidence

  • Transfer as credit to Future Tours

    Exodus allows you to transfer existing payments to a future tour to avoid cancellation fees if you can't travel and inform exodus, 43 days before departure.

  • Low Deposit

    Exodus requires a minimum deposit of 25% or the full booking value, whichever is less, with the final balance not due until 90 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of exodus charges.

    Up to 70 days before tour starts: Forfeit 100% of deposit.

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