
Tuscany Cycle Siena & Chianti
Ride through Tuscany’s classic towns of Siena, San Gimignano and
Montepulciano
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Reviews 34 Reviews5/5
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Vacation Style Holiday Type
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Cycling
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Activity Level Moderate
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Group Size Small Group
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.
* All breakfasts
* 7 nights accommodation at 3 star hotels with en suite facilities
* All transport and listed activities
* Tour leader throughout
* Airport transfers (at designated times)
* Local bike rental
- Flights
- Single Accommodation (available on request, inquire for supplement)
- E-Bike (available on request, inquire for supplement)
- Local taxes (approx. EUR 10 per person, see Trip Notes)
Highlights
- Enjoy famous Tuscan cuisine and wine
- Explore the cultural cities of Siena and Florence
- Visit some of Tuscany’s most beautiful hilltop towns
- 7 nights at 3 star hotels with en suite facilities
- 5 days cycling with partial vehicle support (limited seats)
- Group normally 6 to 16, plus leaders. Min age 16 years
- 95% tarmac, 5% easy gravel roads
- Day 1 Start San Quirico.
- Day 2 Circular ride through classic Tuscan countryside via Pienza, the wine town of Montepulciano and thermal spa village of Bagno Vignoni.
- Day 3 Ride through vineyards and the walled town of Murlo to Siena.
- Day 4 Free day in Siena to explore or relax.
- Day 5 Ride via Gaiole and Radda to Castellina in Chianti.
- Day 6 Circular ride through the Chianti hills via towers of San Gimignano and Monteriggioni.
- Day 7 Cycle to Florence via Panzano and Greve in Chianti.
- Day 8 End Florence.

Hotels
You will spend 7 nights in family run and comfortable 3-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.
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.
This trip is classified Road.
Activity Level: 3 (Moderate).
Please see the introductory pages of the cycling holidays brochure or our website for more important information on classification and grading.
This region is famous for its rolling hills, so be prepared for some climbing in places. This trip will require a moderate to good level of fitness as the area and rides are on undulating roads varying from 2km hills to 9km hill stretches on some days.
Days 3 and 6 falls into the upper category of moderate grade riding, including some steep sections up to 10-25%.
Distances per day vary from 50-70km. There are no transfers to or from hotels on this trip: all the rides are designed to be door-to-door.
We aim to use quieter country roads where possible, but sometimes we need to pass busy sections surrounding towns. The most scenic routes are on tarmac, with occasional stretches of dirt/gravel roads (locally known as ‘white roads’).
5 days cycling, average 58km/day (36 miles), full vehicle support.
Terrain: 95% tarmac, 5% easy gravel roads. Approx. 300 km in total.
Most days rides will be broken up by morning coffee, lunch and afternoon gelato stops. Usually section of 5-15 km will be done between re-grouping. The leader will keep the group together during busier/complicated sections, but on straight roads, cyclists are free to ride at their own pace.
Summer months
Tuscany can be very hot during summer months, especially from June to August but heatwaves can happen also in April and May. During summer months temperatures can possibly reach high 30s (degC). We will try and start our days earlier, when possible, to avoid the hottest hours of the day but please be aware that temperatures and humidity will be high. You should feel comfortable and be used to cycle in the heat. Presence of mosquitoes in summer may increase (significantly), we recommend taking mosquito repellent with you.
Please note that at times, especially during summer months, the arrival airport pick up time can be late in the evening. In this instance you will have additional time to spend in Pisa. Leader will take care of all arrangements in terms of transport from/to the airport and the city centre and luggage storage. It may also happen that, for logistical reasons, on return we will have to be at the airport earlier than normally scheduled. This will mean a longer waiting time before checking in.
Package Confirmed Dates | Trip Status Trip Status | Price (PP) Excluding Flights | Price (PP) Including Flights | |
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May 15, 2021
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Available |
$2,149.00 |
N/A |
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May 22, 2021
|
Available |
$2,149.00 |
N/A |
|
May 29, 2021
|
Available |
$2,149.00 |
N/A |
|
June 5, 2021
|
Available |
$2,149.00 |
N/A |
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June 12, 2021
|
Available |
$2,149.00 |
N/A |
|
July 24, 2021
|
Available |
$2,149.00 |
N/A |
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August 14, 2021
|
Available |
$2,149.00 |
N/A |
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August 28, 2021
|
Available |
$2,149.00 |
N/A |
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September 11, 2021
|
Available |
$2,149.00 |
N/A |
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September 18, 2021
|
Available |
$2,149.00 |
N/A |
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September 25, 2021
|
Available |
$2,149.00 |
N/A |
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October 2, 2021
|
Available |
$2,149.00 |
N/A |
CYCLE THROUGH SIENA & CHIANTI
What was the most inspirational moment of your trip?
It has to be the ride into Sienna and arriving in the main sqaure. It's also pretty amazing arriving in Piazza Michelangelo in Florence. The Piazza del Miracolos in Pisa takes some beating. or maybe it was the first taste of Vino Nobile de Montepulciano?What did you think of your group leader?
The group leaders Mike and Rudy were both great, very experienced and committed to making sure that everything went smoothly and that everyone in the group had a great time. Nothing was a problem and they worked hard all the time to make things even better.Do you have any advice for potential travellers?
The distances are not long but it's quite up and down. You'll enjoy the trip more if you do some hill training before you go. There is an optional hill to ride up on the return from San Gimignano - the incline is gradual so you can certainly complete it and it's a great feeling when you reach the top and look down where you've come from!Is there anything else you would like to add?
There is a local pasta called pici, which is like a fat spaghetti. It's only available freshly made so this is the only place you can get it. It's really delicious with pecorino cheese and black pepper.TUSCANY: CYCLE SIENA & CHIANTI
What was the most inspirational moment of your trip?
Cycling the final climb into Siena, after a 70km ride, to arrive at the famous Piazza, then to be guided through the Siena streets by Allessandro. A most memorable day. Wonderful.What did you think of your group leader?
Already voted for the awards! Excellent.Do you have any advice for potential travellers?
Although this is described as "B" Moderate, there are some climbs (otherwise described as "undulations") but the idea is that you go at your own pace and enjoy every moment of every day and especially the wonderful scenery. There is absolutely no pressure to keep up with anyone else in the group. It is very much a "no pressure" trip, but if you are willing to push yourself, it is a great fitness challenge. ps padded cycling shorts are a must!Is there anything else you would like to add?
One of the best, if not "THE" best holiday, which we have ever had. We'll be back...soon.Tuscany: Cycle Siena & Chianti
What was the most inspirational moment of your trip?
A 5km hill becoming fairly easy by the end of the week (goes to show how much your fitness level increases during the week.) Cycling into the cobbled medieval streets of Sienna and down into the main square. Cycling through the vineyards and quaint villages of Chianti. Having a very good reason to eat twice as much as usual, since we had to 'refuel' for the next day. Discovering that other members of the group are just as obsessed with food as I am. Realising that I can still make it up a hill after a complimentary shot of limoncello from a restaurant at lunch time.What did you think of your group leader?
Radu and Alejandro were fantastic leaders and experienced cyclists. They worked brilliantly both together and independently. They also prepared some fantastic picnics for lunch stops and provided good snacks for refuelling. They knew the best places to eat in town (and where to get the best gelato.) Everything went smoothly and the group had a fantastic time.Do you have any advice for potential travellers?
My first cycling holiday, so I'm glad I had a reasonable level of fitness for the 'undulating' countryside, 'spicy hills' and hilltop towns/villages (and there's an optional 7km non stop hill at the end of a long cycling day too). I wish I'd taken a gel seat cover as well as padded shorts (I didn't take my own saddle). I probably would've taken clip on shoes too.Is there anything else you would like to add?
The pici (fat spaghetti) is amazing! Prosecco is cheap too.Cycling in Tuscany, Siena and Chianti
What was the most inspirational moment of your trip?
The day we spent in San Grimignano when it was too wet to ride (although we enjoyed the cycling a lot).What did you think of your group leader?
The group leaders, Radu and Natalie, were excellent. They were very knowledgeable, well-organised and good at solving problems.Do you have any advice for potential travellers?
Tuscany is quite hilly. It might be a good idea to try some hills in England first. If a hill is really formidable you can get a lift in the support vehicle so you don't need to worry about the hills too much. In September the weather in Tuscany can be wet. Taking good quality waterproofs is a good idea because although it may be possible to take a day off cycling because of bad weather there will be days when you have to cycle whatever the weather because you need to get to the next destination.Is there anything else you would like to add?
Overall, this was a fantastic holiday.Cycle Tuscany and Chianti
What was the most inspirational moment of your trip?
Cycling in to all of the beautiful Tuscan towns in which we stayed were inspirational. However, our triumphal entry to our very own room with a view, Florence was extra special.What did you think of your group leader?
Alex and Simon were both extremely encouraging, professional and knowledgeable. Being relatively new to cycling I found their advice and guidance plus technical tips extremely useful.Do you have any advice for potential travellers?
Buy yourself a little handle bar bag (available on line) they are big enough for everything you need with you throughout the day and for any extras the van is never too far away. If you want to treat yourself to a commemorative cycling jersey go to the little sports shop on the square in San Gimignano they're expensive in all the towns but slightly cheaper there and well worth investing in as a great memento of the trip.Is there anything else you would like to add?
Don't waste time thinking about this holiday just get booked. You won't regret it. I went in early October and had excellent cycling weather.