- Explore the cultural cities of Siena and Florence
- Enjoy Tuscan cuisine and wine
- Visit some of the most beautiful hilltop towns in the region
- Ride along the scenic country roads of classic Tuscany
Tuscany: Cycle Siena & Chianti
On Offer:
Receive a $100 digital Patagonia Gift Card with any guided trip purchased in September. Learn more.
8 Days
from
8 Days
from
Incl. taxes
Excl. flights
Cycling
Itinerary
San Quirico D'Orcia or Pienza Florence
Fly to Pisa; transfer to the Orcia Valley
Fly to Pisa; transfer to your accommodation in the Orcia Valley (approx. 2hrs 30 mins).
Start at your hotel in the Orcia Valley
We start in the Orcia Valley, staying in one the local hilltop towns, San Quirico D’Orcia or Pienza. There’ll be a welcome briefing at the hotel, where we gather as a group to go over the trip ahead.
Circular ride through classic Tuscan countryside via the wine town of Montepulciano and thermal spa village of Bagno Vignoni
Today we enjoy a circular ride in the Orcia Valley. Taking in Pienza and San Quirico d’Orcia, we cycle to the beautifully situated wine centre of Montepulciano, best known for producing vino nobile. We then head towards the medieval village of Monticchiello and on to the well known thermal bath of Bagno Vignoni, before making our way back to the hotel.
Ride through vineyards and the walled town of Murlo to Siena
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.
If staying in Pienza (26 August 2023 departure), today’s ride is an extra 6mi (10km).
Free day in Siena to explore or relax
Siena is one of the best-preserved medieval towns in Italy and home to the grand Piazza del 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 (cathedral). Alternatively, you may choose to head out for an unguided ride.
Ride via Gaiole and Radda to Castellina in Chianti
From Siena, we head directly into the heart of Chianti. Our picturesque route takes us via some lovely small villages and hamlets, plus spectacular vineyards and castles, such as Castello di Brolio. Here there is the option to taste some of the finest regional wines. We then cycle on to Gaiole for lunch and, after a gelato stop in Radda, follow our final section to Castellina in Chianti, where we stay for two nights.
Circular ride through the Chianti hills via towers of San Gimignano and Monteriggioni
From Castellina, we ride through rolling countryside before taking a scenic descent into the lower valley. From Poggibonsi, we head towards the distant towers of San Gimignano, nestled between hills and small hamlets. The Unesco-recognised town, famous for its towers, vernaccia wine and saffron, is one of the most visited and interesting sights in Tuscany. We spend a few hours enjoying the atmosphere, walking by the walls and admiring the high towers. Our return involves a long but beautiful climb before reaching Castellina and a well-deserved gelato.
Cycle to Florence via Panzano and Greve in Chianti
Our final ride passes through Panzano towards the market town of Greve in Chianti. This is considered one of the most scenic roads in Tuscany, which links Florence to Siena via the Chianti hills. On arrival in Greve in Chianti, we have time to admire the triangular piazza that hosts the Chianti wine festival before heading towards Strada and Impruneta, known for their terracotta production. In Impruneta, we stop for lunch. We finish by taking a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo. We will arrive in Florence in the early afternoon, giving you time to start exploring this wonderful Renaissance city, including the cathedral and Baptistery of Saint John. Don’t miss the Ponte Vecchio, a medieval stone bridge lined with jewellers, which connects the two banks of the river Arno.
Transfer to Pisa; fly to London
Transfer to Pisa; fly to London (approx. 1hr 15 mins).
Please note that at times, especially during summer months, the inbound flight 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.
End Florence.
The trip comes to an end after breakfast. However, if you’d like a little longer to explore this magnificent city, please speak to your sales representative.
Share Your Photos...
#ExodusTravels
Essential Info
Is this trip for you?
This trip is classified Road and Activity Level 4 (Moderate/Challenging). Please see our website for more information on classification and grading.
This region is known 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 1.2mi (2km) to 5.6mi (9km) hill stretches on some days.
Days 3, 5 and 6 fall into the category of Moderate/Challenging riding, with elevation gains of more than 3,281ft (1,000m) and some steep sections up to 10%-25%. Daily distances vary from 32mi-47mi (51km-75km). There are no transfers to or from hotels on this trip: all the rides are door-to-door. We use quieter country roads where possible, but sometimes we need to pass busy sections surrounding towns. The most scenic routes are on paved roads, with occasional stretches of dirt/gravel roads (locally known as white roads).
Five days cycling, average 37.5mi (60km) per day, partial vehicle support (limited seats).
Terrain: 95 percent paved, five percent easy gravel roads. Approximately 193mi (302km) in total.
Most days, rides will be broken up by morning coffee, lunch and afternoon gelato stops. Usually sections of 3mi-9mi (5km-15km) will be done between regrouping. 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
Tuscany can be very hot during summer (June to August), but heatwaves can also happen in April and May. We try to start our days earlier, when possible, to avoid the hottest hours, but temperatures and humidity will be high. You should feel comfortable and be used to cycling in the heat. The number of mosquitos may increase significantly in summer, so bring mosquito repellent with you.
Hotels
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
- Florence: Hotel Classic
We can arrange single rooms throughout the trip (subject to availability). Please check with your sales representative for availability and prices.
Trip Experts
Michele Quaresimin
Expert Leader: Italy
Reviews
Add your own reviewGreat trip, great scenery, lovely gelato
We just returned from this trip and would highly recommend to anyone who enjoys the Italian way of life, cycling in great countryside and beautiful scenery, doesn’t mind regular climbs.
We had great company from a lovely group of fellow cyclists and stayed in reasonable hotels en route. We like trips that are door to door with no transfers. This route was particularly good as each hotel was a 2 night stay with a couple of circular rides on day 2 – just good not to have to pack and move on every day.
Most Inspirational Moment
Wouldn’t describe it as inspirational as such but highlights were: - marvellous scenery on every ride - cycling into Siena and Florence then enjoying the best of each city - off the bikes - gelato at the end of most rides - we earned them! - amazing weather for early October
Thoughts on Group Leader
- good - Cesare was pleasant friendly and helpful. Made a couple of mistakes when a couple of the group were lost off - should have waited or left one of the group to wait and direct them. Wasn’t a mistake he made again. Chose good places for us to eat together each day. Had only done a couple of Exodus trips previously so didn’t. Follow the Exodus way in relation to issues such as kitty for tips etc but maybe good to be different
Advice for Potential Travellers
Definitely need to be prepared for the hills - it was a genuine moderate to challenging route, with regular climbs, some lengthy and more challenging in the afternoons when hot. Do some training on hills in advance. Take snacks for a sugar boost when needed.
Suggestions
Our group were lovely people, but having a mix of e-bikes and manual bikes seems to affect the dynamics of the group. I do wonder if trips are better offered as e-bike or manual bike trips. Those of us riding under our own steam obviously took longer on the climbs, keeping the those with added power waiting. Just feels different as it seems to break the group into two parts.
Cycling past the cypress trees
Very enjoyable trip, a great part of the world to go cycling.
Most Inspirational Moment
Seeing view of Florence at the end.
Thoughts on Group Leader
Martino organised everything very well and tried his best to help someone whose luggage did not arrive at all. Excellent knowledge of gelato stops!
Advice for Potential Travellers
Handlebar bags are provided so plenty of space to store items on the road. Quite a few climbs (all the villages and towns are on hills) so bring some energy bars.
Suggestions
Check out L'Eroica website.
Highly recommended
From the arrival on day one until the final departure this trip was so well run I felt totally taken care of from the cycling including the detailed briefings and advice, to the organisation of accommodation and the group meals. What a great bunch of fellow cyclists and the two guides, Jon and David, did an excellent job looking after us (and our bikes!). The cycling was challenging but no-one was made to feel inadequate if they finished later than others (that was often me!!) – everyone helped and encouraged each other and the guides kept an eye on everyone to ensure we were all safe at all times. There was plenty of time to stop and take breaks and refreshments which helped with managing some of the longer trip days. The rest day in Siena was fabulous – what a great place to spend a day! I cannot speak highly enough of this trip – it’s my first group cycling adventure but I am sure it will not be my last although I am now worried about finding something that will live up to the high standard set by this trip!! If you are thinking about doing this trip and are up for doing a few hills in return for some great views and great food, I would highly recommend you give this a go!!
Most Inspirational Moment
We all managed to complete a 9k hill climb with the help and encouragement of the leaders - it was a slog but rewarded by the best gelato at the top! I also learned a bit more about how to use my gears and pace myself up a hill and can't wait to put my newfound experience into practice in future. However, there were many inspirational moments I could think off but mainly what a great bunch of people were on the trip - we were a diverse bunch in terms of age and background but everyone just got on really well and that helped to make the holiday into an unforgettable experience.
Thoughts on Group Leader
Both leaders, Jon and David, were fantastic. They shared the work both cycling with us and providing van back up, looked after the bikes, provided on-the-road guidance and advice, organised the meals and ensured everyone felt included in all the activities - they even organised a small celebration as one group member was celebrating a birthday during the week. They both had great local knowledge so could explain much about the areas we were travelling through and points of interest. They both worked extremely hard for long days with little time to themselves but remained enthusiastic and engaged the whole time even though they do this week in, week out it never showed.
Advice for Potential Travellers
If you are thinking about this sort of trip, particularly if you are planning to go "solo", I would highly recommend it. Make sure you are fit for the holiday and you will get out of it what you put in.
Suggestions
I would recommend this holiday to anyone; my experience of the whole Exodus process and holiday is excellent and if other trips are to the same standard I would have no hesitation in going with them again.
Fantastic cycling in stunning Tuscany
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!
Most Inspirational Moment
Every moment that I was on the bike!
Thoughts on Group Leader
David and "Vandy" were both great!
Advice for Potential Travellers
Be fit!
Suggestions
The breakfast at the Classic Hotel in Florence was truly dismal. Heyho, everything else was great...but you did ask!
Great cycling in exquisite surroundings
Terrific trip. Just the right combination of decent cycling with culture, food and relaxation. A great opportunity to combine seeing Siena and Florence with some moderate exertion.
Most Inspirational Moment
Completing the long climb up to Castellina was very satisfying. A close second was the view of Florence on first arrival in the city.
Thoughts on Group Leader
David was good - very knowledgeable, well organised, pleasant and approachable. He ran the trip very well and was always helpful.
Advice for Potential Travellers
You need a reasonable level of fitness to do this and some experience of cycling. But it's not all about cycling - there's free time to enjoy Siena, which was a highlight, and the guides take you to some decent restaurants too.
Scenic cycling tour
We very much enjoyed the trip. The countryside was beautiful and cycling was challenging enough but was still fun and rewarding. The food was excellent and the tour guide’s choice of restaurants was very good.
Most Inspirational Moment
Beautiful vineyard covered landscapes.
Thoughts on Group Leader
The guides Jon and David split the responsibilities for leading the cycling and we found them both to be extremely good - very easy to get on with and knowledgable about the area we were travelling through and made sure everything ran smoothly. We have only praise for them.
Advice for Potential Travellers
Be aware of how hot it can become in summer. We travelled early June and it was a warm as we would want it to be for an activity holiday.
Suggestions
My only criticism was the farmhouse in Castellina in Chianti could benefit from some updating in the rooms/bathrooms.
Cycling and Chianti
A well organised cycling holiday with excellent accommodation, encouraged to gel as a group in both cycling and eating experiences and enjoy the wonderful scenery en-route.
Most Inspirational Moment
Probably surviving the 25% incline up to the wine tasting experience! Otherwise experiencing the IL CAMPO and walking around the Fort and Garibaldi memorial in Sienna.
Thoughts on Group Leader
An excellent leader with good local knowledge and mixing with the whole group.
Advice for Potential Travellers
The trip is rated as "Moderate" cycling ability but some of the "undulations" require a good level of fitness, but for encouragement there is usually a gelato reward at the end.
Suggestions
This is a "no worries" exploring experiences, where you are well looked after from arriving and departing Pisa airport. I particularly enjoyed the arrangement for having 2 night stays through the holiday and not having to pack and depart after breakfast everyday.
Falling in love with Tuscany...
This was my 4th Exodus cycling holiday and they deliver consistently good holidays. Tuscany is absolutely stunning and, combined with fantastic food, wine and gelato, makes a great holiday destination for cyclists. The accommodation on this trip is very good and it is made more relaxing by staying 2 nights in the 3 first hotels with the final night then in Florence.
Most Inspirational Moment
I wouldn't necessarily talk about inspiration but I did enjoy a glass of chianti classico most lunchtimes and that was certainly a treat!
Thoughts on Group Leader
The group was very mixed ability and the group leader, Jon, kept everyone safe. However, on previous Exodus trips the leader has given more local knowledge. I didn't get the impression that Jon had a lot of local knowledge, other than cycling knowledge which he has in abundance. He did talk a lot but I felt that this was often at the expense of getting on the road or spending time on route.
Advice for Potential Travellers
It's stunning - go but do some hill training in advance!
Amazing adventure!
This was my first cycling tour and tour with Exodus. I had an amazing experience! The trip was well planned and I feel like it had the prefect balance of cycling, exploring towns on foot and good food. The level of difficulty was more than I thought. I trained in advance, which served me well, but I recommend others do the same, especially if this is your first bike tour.
Most Inspirational Moment
Getting to the top of each hill is so rewarding. You definitely earn the views!
Awesome trip!
Fantastic trip, with Fantastic people!
This was my first Exodus cycle trip, and for a Level 3, not only myself, but many others in the group found it a very challenging trip. The roads in this part of Italy, is either “up” or “down”…so with the weather being over 30C each day, each day was a bit challenging. I would definitely rate this trip higher than “Moderate”, but having said that I thoroughly enjoyed the beautiful scenery, Tuscan hills, the food & wine, and all that Tuscany offers!
Can’t wait to do my next Exodus Cycle tour!!
Most Inspirational Moment
Our group was so much fun! We all shared similar ages and cycle abilities, some more than others, but getting together each evening for dinner was a highlight! Love to cycle with this group again!
Thoughts on Group Leader
Both David & Rebecca (Becks) were awesome leaders! They kept the team together, and always booked some awesome local restaurant for all of us to dine together. They always prepared us for the next 10-15kms, so breaking up the day with stops and lunch breaks along the way, made it for great cycle days.
Advice for Potential Travellers
This cycle trip is not for the "light hearted"! You are climbing many long hills, and cycling down many windy roads. I would say recommend doing long steep hill rides before you venture to Tuscany! Having said that, it is so beautiful and rewarding...so definitely go, but make sure you get those hill cycles in before you go on this trip!
Start
Finish
Availability
Adult Price From
Optional Single Supplement
Saturday Saturday
11 May 2024 11 May 2024
Saturday Saturday
18 May 2024 18 May 2024
Availability Guaranteed (Available)
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
18 May 2024 18 May 2024
Saturday Saturday
25 May 2024 25 May 2024
Availability Guaranteed (Available)
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
25 May 2024 25 May 2024
Saturday Saturday
01 Jun 2024 01 Jun 2024
Availability Available
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
01 Jun 2024 01 Jun 2024
Saturday Saturday
08 Jun 2024 08 Jun 2024
Availability Available
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
08 Jun 2024 08 Jun 2024
Saturday Saturday
15 Jun 2024 15 Jun 2024
Availability Guaranteed (Available)
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
31 Aug 2024 31 Aug 2024
Saturday Saturday
07 Sep 2024 07 Sep 2024
Availability Available
Adult Price From CAD 3,795
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
07 Sep 2024 07 Sep 2024
Saturday Saturday
14 Sep 2024 14 Sep 2024
Availability Guaranteed (Available)
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
14 Sep 2024 14 Sep 2024
Saturday Saturday
21 Sep 2024 21 Sep 2024
Availability Guaranteed (Available)
Adult Price From CAD 3,795
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
28 Sep 2024 28 Sep 2024
Saturday Saturday
05 Oct 2024 05 Oct 2024
Availability Available
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
05 Oct 2024 05 Oct 2024
Saturday Saturday
12 Oct 2024 12 Oct 2024
Availability Available
Adult Price From CAD 3,745
Optional Single Supplement +CAD 779
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesWould you like to include flights with your booking?
- ATOL protected
- Competitive flight prices
- Full refunds in the event of FCDO cancellations or major disruption at your UK departure airport
- Specialist support to rearrange flights and transfers
- Regional flights available from many UK airports
You may also like
The Adventure Begins Here
Get regular inspiration straight to your inbox from Exodus' experts.
Tuscany: Cycle Siena & Chianti
8 Days
from
8 Days
from
Incl. taxes
Excl. flights