Current as of: July 23, 2024 - 14:13


Tuscany: Cycle Siena & Chianti Trip Notes

  • Ways to Travel: Guided Group, Private Group Adventures
  • Destination: Italy
  • Programmes: Cycling
  • Activity Level:

    4 out of 7 - Moderate & Challenging

  • 8 Days: Flight Inclusive
  • 8 Days: Land Only
  • Ages: 16+
  • Trip Code: MWI
  • Carbon Footprint: 13kg CO2e

Trip Overview

Ride along the back roads of classic Tuscany­­

The Tuscan landscape is one of the most evocative and romantic in Europe, with cypress tree-lined roads, olive groves, vineyards, ancient hilltop 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. We ride through historically diverse areas of Tuscany, such as the Chianti hills and beautiful countryside around Montepulciano. Riding north, we discover a wonderfully scenic region, home to some of Tuscany’s most beautiful towns and villages. We then enjoy the magnificent Piazza del Campo in Siena before biking past the towers of San Gimignano and on to our final destination in Florence. Following country roads wherever possible, we mix point-to-point and circular rides to make a perfect cycling tour of this region.

At a Glance

  • Seven nights at three-star hotels with en suite facilities
  • Five days cycling with partial vehicle support (limited seats)
  • Group normally 6 to 16, plus leaders. Minimum age: 16
  • E-bikes available for an additional cost
  • 95 percent paved, five percent easy gravel roads
  • Option to travel by train to your adventure


  • 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

Is This Trip for You?

This trip is classified Road and Activity Level 4 (Moderate & Challenging).For more information on our trip gradings please visit the Activity Level Guidelines page. If you have any queries about the difficulty of the trip please do not hesitate to contact us.  

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 and 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.


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.


The trip has two leaders, one who cycles with the group and acts as a mechanic, helping with any bike problems. The other leader drives the support vehicle and supports the group when cycling on point-to-point days. The vehicle is also used to transport the luggage from one hotel to the next.

Adult min age: 16

Min group size: 6

Max group size: 16



Land Only

  • Start City: San Quirico D'Orcia or Pienza
  • End City: Florence

Land Only Itinerary

Day 1
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.

Day 2
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.

Distance covered: 35mi (56km)

Ascent: 2,969ft (905m); Descent: 2,969ft (905m)

Meals included: Breakfast

Day 3
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).

Distance covered: 43mi (69km)

Ascent: 4,042ft (1,232m); Descent: 4,291ft (1,308m)

Meals included: Breakfast

Day 4
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.

Meals included: Breakfast

Day 5
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.

Distance covered: 32mi (51km)

Ascent: 3,307ft (1,008m); Descent: 2,405ft (733m)

Meals included: Breakfast

Day 6
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.

Distance covered: 47mi (75km)

Ascent: 3,957ft (1,206m); Descent: 3,957ft (1,206m)

Meals included: Breakfast

Day 7
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.

Distance covered: 32mi (51km)

Ascent: 2,356ft (718m); Descent: 4,012ft (1,223m)

Meals included: Breakfast

Day 8
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.

Meals included: Breakfast

Ascents, descents and distances: All ascents, descents and distances listed in the daily itinerary have been measured by our local partners or tour leaders, in many cases with satellite-based mapping software. However, different GPS measuring devices can give differing results, particularly on winding paths or in mountainous terrain. Measurements stated throughout these Trips Notes are given to help you understand the types of terrain and distances you will encounter. Timings stated will vary depending on the pace of your group.



Tuscany: Cycle Siena & Chianti

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: Wellness Hotel Casanova or Relais 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.

Please note that during peak travelling periods or in case of last minute bookings, alternative hotels may be assigned on an individual basis and that supplements may apply.

Single supplement from £ 410

Food & Drink

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.

Tuscan food is authentic and surprising – pizza and pasta are just the tip of the iceberg when it comes to the diverse cuisine on this trip.

  • Starters may include antipasti of cured meats or a crostini di fegato made from toasted bread slices topped with chicken liver pâté .
  • Soup options may include the classic bean dish of zuppa di fagioli or ribollita, a delicious, hearty vegetable and bread soup.
  • For mains, you might try the truffle-infused pasta dish tagliatelle al tartufo or a mouth-watering T-bone steak delicacy known as bistecca alla Fiorentina.
  • End your meal with cantucci biscuits dipped into a glass of the sweet dessert wine known as vin santo for a true taste of Tuscany.

While Tuscan cuisine has a strong meat focus, vegetarians can be well catered for. Please inform us of any dietary requirements at the time of booking.


Your luggage is transferred from one hotel to the next using the support vehicle, which follows the group during the rides as well.

Weather & Seasonality

Italy has  plenty of sunshine and warm temperatures from spring through to autumn. Summer departures will usually have hot weather, with highs around 35C (95F). April-June and September-October 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.

Joining Instructions

Key information

Recommended arrival time: You can arrive at any time today. There will be a welcome briefing in the evening, but if you miss it the leader will update you separately
Airport: Pisa Aiport (PSA)

Tuscany: Cycle Siena & Chianti

Getting to the start hotel

The start hotel is approximately a 2hr 30min drive from the airport. Your options for this journey are:

Take an Exodus transfer 

Exodus provides one group arrival transfer from the airport, which is timed to coincide with the arrival of a chosen flight from London, UK. You may join this transfer at no extra cost, provided you can be at the airport before the transfer leaves. Speak to your sales representative for the group arrival transfer times or to arrange a private transfer.

Make your own way 

It’s possible to reach the start hotel by public transport, but connections are limited. We therefore recommend joining the group transfer where possible. If not, you can book a private transfer before departure through your sales representative, which will cost around €350. If you would like further information on joining this trip, please speak to your sales representative.

Catching your return flight

The trip ends in Florence, a 1h 15min drive from Pisa Airport. There’s a group departure transfer to the airport for customers who Exodus booked onto a chosen flight to London, UK. Please speak to your sales representative if you wish to join. If the group departure transfer does not suit your flight time, speak to your sales representative to arrange an alternative transfer.

For UK-based customers catching the group flight

At times, especially during summer, the return flight can be late in the evening. In this case, you will have additional time in Pisa. The leader will take care of luggage and transport from/to the airport and city centre. 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 check-in.


Full joining instructions including local emergency numbers will be sent to you as part of our Final Joining Instructions. If you do not receive these at least a week before departure, or require them earlier please contact our office or your travel agent.

Location start: San Quirico D'Orcia or Pienza
Location end: Florence

What To Take

Essential Equipment

  • Electrolyte sachets (for summer)
  • Sunscreen

Water bottle: while mineral water is available in restaurants and shops, it’s safe to drink the tap water in hotels, so remember to bring refillable water bottles and keep hydrated during the day.

Optional Equipment

  • Swimming costume for swimming pools available at several hotels

Equipment Hire

Included standard bike
The standard bike for this trip is a Musing Twinroad, an aluminium hybrid bike.

We will take your height at the time of booking to reserve equipment. If you have a preferred bike size, please request when booking.

E-bike upgrade
Electric bikes are available on this trip; prices from £190/US$270/360 Canadian dollars. Speak to your sales representative for more information.

Bringing your own bike
If you’d prefer to bring your own bike, please advise us at the time of booking and you will receive a discount on the price of the trip. However, you will be responsible­­ f­or any extra baggage charges; assembling and disassembling your bike; and bringing along spare parts and any tools specific to it. You should also ensure you have adequate insurance to cover loss, damage or theft.

Accessories and clothing

Bringing equipment from home
You’re welcome to bring your own equipment, such as SPD pedals or clipless pedals, your own saddle (excluding the seat post), or gel saddle cover for the hire bikes. Your leader will help you fit these when bikes are distributed.

Helmets are mandatory for everyone on a guided Exodus cycling trip. You must bring your own as, following best safety practice, they are not available for hire.

Cycling clothing
For this cycling trip we recommend:

  • Padded cycling shorts: For destinations with more modest cultures, we also recommend loose ‘over-shorts’ for riding or rest stops
  • Eyewear: Either sunglasses or eye protection with clear lenses to protect the eyes while riding
  • Cycling gloves: Especially for riding off-road or on rugged surfaces
  • Cycling shoes: Cycling is more efficient with stiff-soled shoes. We don’t recommend open-toed shoes or sandals
  • Small close-fitting backpack or bum bag (fanny pack): To keep spare clothing or essential items to hand during the ride
  • Waterproof jacket and long cycling trousers, plus a warm top

Practical Information


Remember to check the expiration date of your passport if travelling internationally. Many countries require your passport to be valid for at least six months after the date of your scheduled return.



Travellers from the UK, US and EU normally do not need a visa to enter Italy. Please note, visa requirements often change and it is your responsibility to obtain any required visas for this trip. Therefore, we recommend that you check with the nearest embassy or consulate of your chosen destination(s), including any countries you may be transiting or transferring through.

Some local governments provide guidance on what visas their citizens need. To help, we’ve gathered a selection of useful links below.

• Australia:
• Canada:
• United Kingdom:
• USA:

Please note: it is compulsory to carry ID with you at all times in Italy.

Vaccinations and Health


There are no required vaccinations. However, you may want to consider vaccinations for tetanus, rabies and tick-borne encephalitis. Please confirm with your doctor or travel clinic.

If you’re a UK citizen, please note that your UK-issued European Health Insurance Cards (EHIC) are still valid and offer the same cover as the Global Health Insurance Cards (GHIC) in the EU. This gives you medical care at a reduced cost, and in some cases for free, in many European countries, but should not be considered a substitute for adequate insurance. Once your EHIC has expired, replace it with a GHIC.

Local Time

Italy's time zone: Europe/Rome (UTC +02:00)


Italy's electricity: Plug types C (two round pins, European standard), F (two round pins), and L (three round pins in a row) – 230V, 50Hz

Tuscany: Cycle Siena & Chianti


Italy's currency: Euros (EUR)

ATM Availability

ATMs are available in most towns. Payment by credit card is normally fine, but not accepted everywhere.

Extra Expenses & Spending Money

For the meals not included, allow €15-20 for lunch and €25-€35 for dinners. The exact amount spent depends entirely on the type of restaurant visited and the menu chosen.

Optional sightseeing:

  • Accademia Gallery in Florence: €16 (including €6 booking fee)
  • Siena Cathedral: €8 (cathedral and Piccolomini Library) or up to €22 when also including the crypt, baptistry, museum and viewpoint (including €1 booking fee)
  • Uffizi Gallery in Florence: €16 (including €4 booking fee). If you would like to visit the Uffizi, we recommend that you prebook your ticket online to avoid lengthy queues. Tickets can be purchased at

All accommodation is included in the price of the trip but hotel taxes in Italy must be paid locally when checking into the hotel. Please allow between €19-23 for the week (depending on the season) to cover this. In some cities, children and people aged 75 or over are exempt from this tax.


Although optional, a tip for the leaders at the end of the trip is greatly appreciated. As a starting point, we suggest €25 per person for the leader. It is also customary to tip private bus drivers (we suggest from €15 per person for the week).

People, Places & Planet

We work hard to create trips that have a positive impact on the people and places we visit and look after the planet we explore. Learn more about our sustainable travel ethos and practice here and find out about the work of the Exodus Travels Foundation here.

Some sustainable travel highlights of this trip include:


How this trip helps improve life for local communities.

  • Local guides keep you well informed about local traditions and cultural-social sensitivities.
  • This trip brings income and opportunity to the destination community through the inclusion of locally owned hotels, restaurants, and other enterprises, and by championing locally produced food wherever possible. This trip stays in four family owned hotels.
  • Read more about our other initiatives here.


How this trip helps protect and conserve local landscapes and nature.

  • By travelling in a small group we ‘tread lightly’ to minimise our impact on local resources and the environment.
  • We work with our partners on the ground to proactively reduce waste; this includes eliminating all single-use plastic water bottles by providing refills for reusable bottles.
  • With our partners, Rewilding Apennines, we rewild 100 square meters (1,075 sqft) of land per passenger who travels with us.
  • Read about our commitment to nature protection and restoration here, including our rewilding commitment for every customer who travels with us.


How we seek to keep the carbon footprint of this trip low.

  • Accommodation and restaurants in the itinerary use locally sourced food which has not been transported long distances.
  • As this is s cycling holiday it provides a low impact way of exploring the destination.
  • Read about our climate action here, including our carbon reduction and compensation commitments.

Tips for sustainable travel on this trip

  • Leave no trace: we do all we can to ensure we leave no rubbish in the wild and beautiful places we visit; we ask that you do the same. If there are no recycling facilities in-country, consider bringing recyclable materials home with you.
  • Plastic waste reduction: please bring a reusable water bottle on this trip, also consider avoiding single-use hotel toiletries, which generate a large amount of plastic waste.


Important Information

Your safe participation 

When booking this trip, you should be confident in your ability to participate in all activities described in these Trip Notes. If you have any doubt about your suitability, please call the Exodus office and ask to speak to one of the experts on this itinerary. 

Although our leaders are well trained to deal with different capabilities, if they have any concerns about someone’s ability to safely take part in an activity, or their impact on other people’s enjoyment, we authorise them to take necessary action which, in some circumstances, may involve asking someone to miss that activity. 

By booking this trip you agree to our Booking Conditions which clearly state that our leaders have the authority to do this. In these rare instances we will ensure anyone sitting out is safely provided for and offered alternative options where possible. Refunds will not be provided for activities missed and customers may be liable for additional costs incurred. 

How to Book

  1. Check availability: Go online to check availability, or contact us by phone or email.
  2. Secure your place: You can provisionally hold a place on this trip, usually for between three and seven days.
  3. Complete your booking and payment

When you’re ready to book, go to our website for online bookings, book over the phone or you can complete a booking form (available online or on request by calling us). We accept all major credit and debit cards, or you can pay be cheque.

After booking

You will receive your booking confirmation letter and invoice, which includes extra information and guidance about your travel arrangements.

Full joining instructions, including local emergency numbers and details of how to reach the start point, will be sent to you approximately two to three weeks prior to departure. If you do not receive these at least a week before departure, or require them earlier, please contact our office or your travel agent.

Trip Note validity

These Trip Notes are valid from the “Current as” date on page one. They will occasionally be updated after booking and before departure; if there are any updates that significantly impact the inclusions or itinerary, customers will be written to separately. They will also receive a link to the most up-to-date Trip Notes with their Final Joining Instructions before travelling.

The information in these Trip Notes is given in good faith. Where differences exist between the Trip Notes and our current brochure or website, the Trip Notes supersede the brochure and website. All holidays can be subject to unexpected changes; to enjoy them you should be prepared to be flexible where necessary. Occasionally, it may not be possible to follow the itinerary as planned. This may be for a variety of reasons – climatic, political, physical or other. In these circumstances we will make the best-possible alternative arrangements that maintain the integrity of the original itinerary.


Exodus is fully licensed and bonded as a tour operator. We hold Air Traffic Organisers Licence (ATOL) number 2582, issued and bonded with the Civil Aviation Authority (CAA). We are also bonded to the International Air Transport Association (IATA) and we are members of the Federation of Tour Operators (FTO) and ABTA – The Travel Association. This means you can book your Exodus holiday with confidence, as all money paid to us for your trip is fully protected.