Call us now 01722 718444
Italian vineyards.jpg

Tour of Tuscany

Italy Cycle
CycleHotelTerrainYELLOW 3
Enquire Book now

About the Challenge

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.

Tour of Tuscany Cycle

  • Pisa is famous for its 14th-century leaning tower of white marble, but there are other impressive buildings set around the beautiful grass piazza – named the Square of Miracles – of this ancient town. Dependent on flight times, you can enjoy some free time exploring the sights. We meet up later at our hotel, and ensure our kit and bikes are fully prepared for the start of our challenge tomorrow. Night hotel.

    (Lunch not included)

  • We head out on flat roads this morning, which soon rise as we cross the green hills south of Lucca. If you want to challenge yourself fully today, opt for the climb of the Monte Serra just a few miles out of Pisa. This 11km climb is famous as a training ground for the pros, many of whom base themselves around Lucca, and if you’re a keen cyclist you’ll want to test yourself on its slopes. If you prefer to give it a miss, our route continues along the River Arno and heads up through small villages and farmland. We stop for lunch at Vinci, of Leonardo da Vinci fame, and then cross some low hills, which break up what has been a predominantly flat day (Monte Serra excepted!) The scenery starts to become more typically Tuscan as the afternoon progresses, and the roads are only busy in the final flat run-in to the iconic city of Florence, cradle of the Renaissance. Night hotel.

    Cycle approx 110km (68 miles)

  • We head out of this beautiful Renaissance city along the River Arno, and soon start to climb into forested hills as we ride southeast through this wonderful region. A hillier morning sees us tackling long, gradual climbs which contour around the slopes, eventually bringing us onto a ridge which offers wonderful views down into the valley. Our route then undulates through beautiful small towns and villages, many of them with striking old churches and piazzas. We see plenty of vineyards today, many of owned by the ancient farmhouses that dot the landscape. A gentle climb brings us to our hotel at the base of Cortona’s hill; the ancient fortress town lies at the top of the steep road. You are free to ride up, or jump in a taxi to explore it this evening. Night hotel.

    Cycle approx 130km (80 miles)

  • More hills await on this demanding but absolutely beautiful day. We loop south and west, setting off on gently rolling roads which soon climb steadily as we head towards Montepulciano, a gem of a hilltop town known for its wine and gourmet food production. The scenery today fully immerses us in every Tuscan stereotype, as we pass terracotta-roofed villages and villas, climb steeply up through narrow streets into medieval hilltop towns, and pass miles upon miles of vineyards. Our roads, lined at regular intervals with tall, evergreen cypress trees, roll gently through this landscape, with occasional steeper rises, before a longer climb takes us up to Montalcino, known for its Brunello wines. We continue to roll along this stunning Tuscany wine route, before a climb brings us to magical Siena, whose old town is yet another UNESCO World Heritage Site. Night hotel.

    Cycle approx 130km (88 miles)

  • An undulating morning through beautiful valleys awaits us, with yet more stunning views of hilltop towns, vineyards and wooded slopes. A more significant climb takes us up through San Gimignano, a small walled medieval town known for its well-preserved towers and – yet again – its wine! We ride right through this fascinating town, stopping at our very scenic waterstop to admire the views, before continue the climb through the hills. We then enjoy a wonderful descent on tree-lined roads, passing through small villages, before we see the flatter farmland before us. It’s then flat all the way back to Pisa, where we cross the Arno and finish in front of the leaning tower – a memorable end to this wonderful week of cycling, and a perfect way to kick-start our evening of celebrations. Night hotel.

    Cycle approx. 111km (68 miles)

  • After a leisurely breakfast, we have time to relax or wander the Piazza until it’s time to transfer to the airport.

    (Lunch and Dinner not included)

Prices may vary depending on date.

  • Available pricing options

    This challenge requires a minimum of 20 participants
    Fundraising Option
    Registration Fee £199 Fundraising target £2,000 Tour Cost - Airline Taxes - Book now
    Part - Payment Option
    Registration Fee £199 Fundraising target £1,500 Tour Cost £250.00 Airline Taxes - Book now
    Full Payment Option
    Registration Fee £199 Fundraising target - Tour Cost £1,000 Airline Taxes - Book now

    Pricing Explained

    Registration Fee (i)
    Payable on booking

    Fundraising Target (i)
    Paid 10 or 6 weeks prior to trip departure

    Trip Cost (i)
    Payable 8 or 4 weeks prior to trip departure


    • All meals except where specified, and accommodation on a twin-share basis
    • Discover Adventure leaders, mechanics and drivers
    • Full vehicle support throughout the trip
    • Maps and route information
    • Bike transfer from Pisa airport (within agreed time-frame)


    • Any meals specified 'not included' in the itinerary
    • Travel insurance
    • Flights to and from Pisa; transfers to/from hotel
    • Bicycle
    • Cycle helmet (compulsory) and water bottles
    • Personal spending money, souvenirs and drinks
    • Fees for any optional sites, attractions or activities
    • Any applicable surcharges as per Terms and Conditions
    Download Challenge Details

Detailed Information

  • 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.

  • The food provided is plentiful and will give you plenty of energy. Lunches are generally buffet-style while dinners are usually eaten at the hotel. 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.

Preparing for the Challenge

  • 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.


Trips are graded Yellow, Orange or Red, in increasing level of challenge. This trip lies within the YELLOW range.

Yellow colour

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. 

Trip grading explained

Challenges 2019-2020

Get our latest Brochure

Our 2019 / 2020 Challenges Brochure is available by Post or Download