Giro Tuscany Keith Mansfield Picture 1
Giro Tuscany Keith Mansfield Picture 1

Next departure:  Please Call for Details

Best Time of Year: March - October

Max alt:  720m

Dist:  181km

Min age:  18

Duration:  3

Tuscan Giro Cycle Challenge

Bike Adventure

Join us on a truly wonderful journey through the very best of rural and untouched Italy. Experience historic cities, stunning river valleys, winding roads through the scenic Tuscan Hills, and visiting and staying in some of Europe's most famous hilltop towns! Oh and of course - don't forget the wonderful Italian food, wine and hospitality!

Our ride will take us from the gorgeous hilltop resort of Castelfalfi, to San Gimignano, the incredible town in the heart of Tuscany with 14 towers that make the skyline unforgettable; the ride will take us on a wonderful voyage across the cornfields and rolling majesty of Tuscany before stopping in Gaiole in Chianti.

From Gaiole in Chianti we'll sample more beautiful rolling scenery before a challenging ride up to Regello over-looking the Arno valley. The route then winds along the valley side before heading into Florence to enjoy the sights of the Ponte Vecchio and The Duomo di Firenze.

On our final day we cycle up into the surrounding hills North of Florence to sample some of the best views overlooking the city before a transferring back to Pisa.



Day 1 - Travel from UK - into Pisa Airport - or meet early evening directly in Pisa - you will be collected from the airport, and transferred to your hotel in Castelfalfi.

Day 2 - Castelfalfi> Gaiole in Chianti(70km) - Breakfast 08:00 - depart by 08:30 - expected arriving mid to late afternoon - total distance - approx 70km

Day 3 - Gaiole in Chianti> Florence(80km) - Breakfast 07:30 - depart by 09:00 - descend stunning hill top roads before climbing into lunch stop at regello. Long flat ride into Florence. Total Distance - approx 80km

Day 4 - Florence Day loop (40km)- optional day route into the surrounding hills North of Florence with brilliant views over the historic city.

Day 5 - Transfers back to Pisa- Transfers will be supplied back to Pisa airport in time for flights back to the UK.


Route Map


Accomodation confirmed


What is a Level 3.0 Cycling Challenge Like?

These rides are typically multi day rides, with medium distances and undulating terrain. Level 3 rides suit riders who ride regularly, and are looking for something challenging but manageable. In the case of single day events, you can expect up to 8 hours of cycling with breaks. In the case of a multi day ride, you can expect a slightly lower daily duration - but of course - the effort is sustained over a longer period. You should be a competent rider, with regular training outings - both at the weekend and ideally with another session during the week. A 10 week training programme is available for our 3 star rides.


How Fit Do I need to be to join a Level 3.0 ‘Bike Ride’?

You need to have good endurance for these events. You must be used to doing long bike rides in the countryside of 5 hours + and distances of between 45 - 55 miles . You should be doing regular exercise - with some serious cycle training (at least twice per week in the run up to the event). Your typical comfortable cycling speed will be around 21-23 km/hr on flat and gently undulating terrain, and you should be able to cycle at higher speed for up to 1 hour or 25 km (on a road bike). You may also blend in other types of exercise - but for longer periods of time (ie sessions in excess of 1.5 hrs.) - however cycling is the best preparation (obviously!)


Medical Issues

Please note, it is extremely important for this physical challenge that you are in good health. If you have any pre-existing medical conditions, please consider carefully whether you should be joining the challenge. Please ensure you fill in the booking form accurately and honestly, this is important. In the case of serious conditions (epilepsy, diabetes, heart conditions, recent illness or operations), please discuss the challenge with your GP. Please also ensure you notify us of any allergies or similar.

It requires stamina and good aerobic fitness - but good willpower will also come in handy! Failure to disclose medical conditions is a serious omission - that could have serious repercussions on any of our challenges.


Visas / Redtape

None required for this trip (if you are an EU citizen). If from further afield you will need to check requirements.


Included In Trip

Leader (experienced with first aid qualification), Support Vehicle back-up with driver/mechanic, Transfers for bikes to and from airport. Accommodation, Breakfasts.


Excluded From Trip

Flights, Lunches & Dinners, Transport to and from UK airport

Packed Lunches and Dinners are not included - but may be arranged in advance if required.


Equipment Required

Bike Items
Road Bike / Hybrid Bike (with puncture resistant tyres) - please call us for guidance on type of bike on a trip by trip basis
2 X Water Bottles (bladder system/cycle water bottles)
Cycling Gloves, Bike Lock, Neck Scarf, Inner Tubes*, Multi-Tool (with allen keys)*
Day Bag for support vehicle, Small Holdall (for overnight gear)
Bike Lights (front and rear, head torch can be worn)
Saddle Bag (recommended - can be used to carry asterisk* items)
Puncture Repair Kit*, Spare parts for your bike (specialist parts and spokes), Pump (suitable for your valve type)

Helmet (compulsory)
Personal Medikit  Suncream, Plasters, Vaseline, Painkillers, Sunbloc, Insect Repellant


Warm Clothing Medium Weight Softshell, Long sleeve Jersey / insulating layer Lightweight Gloves.

Cycle / Overnight Clothing
Lycra Cycling Shorts, Cotton Shorts, Long Cycling Trousers (Tights/Tracksuit Bottoms)
Cotton T-Shirts for evening
Short Sleeve Cycling T-Shirts (wicking type material) or Cycle Top with rear pockets
Cycling Shoes (approach shoes suitable), Sandals / Spare Shoes for after ride
Casual Evening Wear

Waterproof Clothing
1 Outer Fully Waterproof Jacket (gore-tex, e-vent) - comfortable to cycle in

Travel Documents, EHIC (European Health Insurance Card) Credit Cards, Cash, Local Currency, Mobile Phone, Sunglasses
Snacks for Cycling Days (dried fruits, nuts, flapjacks, cereal bars etc)
Travel insurance (not included), Passport

Make sure you do not ‘over pack’ - bring only what is essential for the trip 
A final kit list will be provided in your ‘Final Joining Instructions’ pre-departure


Safety Information

Full cycling safety guidelines will be issued, as well as regular advice being issued from your cycling leaders.



This itinerary is normally run in either late spring or early summer, or late summer early autumn. At these times the temperatures will be warm without being too sweltering! But, as ever, we should be prepared for the full range of weathers - both hot and sunny and (less likely) cool and showery - be prepared!


Optional Extras

Cultural Experiences-

Instead of cycling you are welcome to partake in some of the culture that makes Tuscany so memorable. Of these options please indicate which would be prefered.

Option 1- Natural Outdoor Hot Springs in Bagni San Filippo, a secluded spa with huge calcium carbonate features and a Wellness centre.

Option 2- A guided walking tour of Tuscanys' most carismatic city Siena, 3 hours guided tour takes in the Piazza del Campo and provides a facinating insight into its history.

Option 3- Wine tasting in one of the finest vineyards Italy has to offer; Bondi Santi in Montalcino with its fine history of fantastic wine.

Option 4- Tuscan culinary class in Florence where you'll experience making fresh pasta, pairing foods with wines and choosing ingredients from a nearby market.

Option 5- Truffle hunting in the woods of Tuscany, you'll join an expert as they take you through how to find truffles. If getting dirty isnt to your liking then join the guide in sampling truffle oils, truffle paste and truffle related products.

Option 6- Artwork tour of Florence; have a guided tour of the most iconic artwork in the world, you will see the original Michaelangelos statue of David, The Accademia museum and the infamous Uffizi gallery.


Notes on Cycling Events

This is our standard range of Cycling Challenges in the UK, Europe and further afield. However, we offer completely tailormade itineraries to your specification. Call us to discuss! Please note that for overseas point to point cycling challenges we can transport soft cases for bike transport - but not hard cases, due to space limitations on board our support vehicles. On all our cycling events, please pack sensibly and bring a reasonably sized soft holdall type bag. To participate in an overseas Adventure Cafe challenge - you must carry Travel Insurance (to be for the activity you are participating in, and to include repatriation to the UK). Please also note that you should have a good level of cycling experience and be competent to handle your bike. We ride on roads shared with other vehicles - and you need to be able to deal with this safely.


Adventure Cafe Booking Terms and Conditions

By booking an event with Adventure Cafe, you agree to these standard terms of booking. Please ensure that you read the appropriate document for your type of event carefully.

Adventure Cafe Terms & Conditions - For all types of event



Guide price




This Challenge is for exclusive group departures – please call us for more information


Event Location

Giro Tuscany Keith Mansfield Picture 2
Giro Tuscany Keith Mansfield Picture 2

Giro Tuscany Keith Mansfield Picture 3
Giro Tuscany Keith Mansfield Picture 3