Tuscany is renowned for its scenery: layers of green hills stretch towards the horizon, covered in olive groves and centuries-old vineyards. This beautiful landscape is dotted with fascinating medieval hilltop towns, crumbling castles and terracotta-roofed villas. The rolling cypress-lined roads are a cyclist’s dream, with fresh views around every bend.
Our circular cycling challenge sets off from Pisa, home of the legendary leaning tower, and takes in the iconic Renaissance cities of Florence and Siena as well as wonderful Tuscan hilltop towns such Montepulciano, Montalcino and San Gimignano. Every day features at least one UNESCO World Heritage Site in this culture-rich region, known worldwide for its art and history.
This is a feast for the eyes and a treat for the legs – a perfect ride for all experience levels.
Challenge Dates and Prices
Challenge Dates and Prices
We are currently confirming new dates and routes for this challenge and these will be updated as soon as available. Please continue to check our website.
Accommodation is usually on a twin-share basis in hotels convenient to our route. Please tell us if you know somebody else on the trip that you would like to share with and we will try our best to accommodate your request. If you don't know anyone else in the group don't worry, we always pair you up with someone of the same gender, and a similar age where possible. We do not charge a single supplement if you are a solo traveller in a shared room.
There may be a limited number of single rooms subject to request, on a first-come first-served basis, after you have booked. Extra charges will apply.
We usually stay in hotels or lodges of a 2-3* standard or equivalent. Standards may vary between the hotels but they are generally comfortable and convenient for our route. Hotels are often on the outskirts of towns to minimise unnecessary extra mileage and avoid traffic.
We like to support local businesses and will source food locally. Lunches will be in restaurants along the route and dinners are usually eaten at the hotel. Do make sure you eat enough to give you the energy for your exertions. Being vegetarian or having other dietary requirements is not usually a problem provided you let us know well in advance. If you know there are plenty of foods you cannot eat you may wish to bring extra snacks from home so you can top up your energy supply.
Your trip will be led by experienced Discover Adventure leaders and support crew, including mechanics. Our leaders are selected for their knowledge and experience, friendliness and approachability, sense of humour and ability to safely and effectively deal with any situation that arises; they are also trained in first aid. The crew will have mobile phones and/or radios where appropriate, medical kit and other safety apparatus where necessary.
The number of crew and support vehicles looking after you will depend on the final size of your group, but the team will be looking after every aspect of your trip whether that’s transporting your luggage, ensuring your route is well-marked, making you lunch and sorting out any mechanical problems. Support vehicles are with the group all of the time, and carry all luggage and spares.
Your safety, and that of the rest of the group, is our highest priority. Our trips are designed and planned with safety in mind. Your crew will be equipped with communication devices (eg phones, radios and/or emergency satellite phones), medical kit and other safety apparatus appropriate to the destination. Our leaders always have access to our 24-hour emergency UK back-up. They are responsible for safety on the trip, and will make any changes to the itinerary they deem necessary, should local conditions dictate. Pre-trip administration - such as medical questionnaires and travel insurance as appropriate - is all done with your safety in mind.
Your booking is part of a group challenge, and the tour costs and fundraising targets listed on our website are based on a minimum number of participants which is shown on the challenge Our typical groups run with approximately 20-30 participants; however you may find your group is smaller or larger than this.
We will confirm at least 12 weeks prior to departure that your challenge is guaranteed to run. Occasionally it may be possible to still run the challenge with less than the minimum numbers, subject to a small group supplement. If we think a small group supplement may be necessary, we will discuss this with you as soon as possible, usually 5 months before your departure date.
Minimum numbers and groups sizes may vary on Bespoke Charity challenges. If you are booked onto a bespoke challenge please contact your charity for full details.
In the unfortunate circumstance that you need to cancel your booking, we would ask that you notify us in writing either by post or email. Your cancellation will be considered effective from the date the notice is received. Registration fees, amendment fees and insurance premiums are non refundable and, depending on your payment option and how close it is to your challenge departure date, you may be liable for a cancellation charge.
Full details of all cancellation charges may be found in the Terms and Conditions of booking.
We plan our trips around the optimal weather conditions, but could still be exposed to bad weather at any time. It is vital you are prepared for all conditions. We provide you with a detailed packing kit-list on registration, as well as details on useful discounts you are entitled to as a Discover Adventure customer. We are always available if you need advice.
This is designed to be a challenge, and it is vital that you train sufficiently for it. We will supply you with a thorough training guide once you have registered. We expect all participants to train hard in advance, but we respect everyone’s limits and do not expect everyone to maintain the same pace. Inadequate training is likely to have an impact not just on your chances of completing the challenge, but enjoying it too - and we want you to have the time of your life!
Our challenges attract people of all levels of experience, fitness and ability as well as all ages and backgrounds. We design our challenges so that everyone can go at their own pace: this is not a race. If you have concerns about your fitness or if you have reduced mobility please do contact us for a confidential chat about whether this challenge is appropriate for you.
For logistical and safety reasons we sometimes need to re-group, so the front-runners may find themselves waiting for the slower ones. Please relax, and remember that this is a team effort that enables people to achieve their personal goals and earn sponsorship.
Travel Insurance is compulsory on our challenges; we strongly suggest that you arrange insurance cover as soon as your booking with us is confirmed. Should you need to cancel on medical grounds, you will need insurance to cover the costs involved (registration fee and any trip costs depending on cancellation date).
You should also ensure that you have adequate cover for the type of challenge you are taking part in as well as medical emergencies, evacuation and repatriation.
You can obtain a quote with Insure to Travel from our website here, or you may choose to take out your own travel insurance, just remember to let us know the policy number and emergency phone number!
For more information about travel insurance, please click here.
Entry requirements vary depending on your destination and nationality. It is your responsibility to ensure your passport is valid, and any visas are obtained in good time. Check the FCO’s advice on entry requirements for your destination to be sure. To find out if you need a visa you can check your requirements using our partner, Visa Machine, website here; please ensure you allow plenty of time.
Your routine UK schedule of vaccinations should be up-to-date (especially tetanus). We recommend you check Fit For Travel for further details. You should always check with a GP or travel clinic for up-to-date travel health advice as it does change.
GRADE | YELLOW
Trips are graded Yellow, Orange or Red, in increasing level of challenge. This trip lies within the YELLOW range.
The grade is determined by factors such as terrain, distance, climate, altitude, etc. Each colour grade has a spectrum which reflects the difficulty of these factors; trip duration, accommodation and living conditions (see icon) are also taken into account.