Giro Tuscany Picture 1
Giro Tuscany Picture 1

Next departure:  Please Call for Details

Best Time of Year: March - October

Max alt:  600m

Dist:  455km

Min age:  18

Duration:  6

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 famous world tourist spot of Pisa and its amazing leaning tower, on a wonderful voyage across the cornfields and rolling majesty of Tuscany.

Our ride takes in the famous hill top towns of San Gimingnano, San Quirico and Montepulciano, before returning via the incredible city of Siena to Florence for one last night of culture before we head for home

On our final day we will transfer to Pisa airport for a return flight home. This ride combines incredible scenery, awesome riding, and delicious food, all in one very memorable package.



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. Assemble / collect bikes, and attend challenge event briefing. Evening dinner + early night!

Day 2 - Pisa > San Gimignano (125km) - Breakfast 07:15 - depart by 08:30 - expected arriving mid to late afternoon - total distance - approx 120km (around 6-7 hours).

Day 3 - San Gimignano > Montepulciano (120km) - Breakfast 07:30 - depart by 09:00 - descend stunning hill top road - then ride to first stop for coffee, then begin to ride through the undulating scenic cornfields en route to Montepulciano, returning to our hotel for the evening. Total Distance - approx 120km - around 7-8 hours

Day 4 - Montepulciano > Siena (120km) - Breakfast 07:30 - depart by 09:00 - expected afternoon arrival by 17:00 latest

Day 5 - Siena > Florence (110km) - One more epic day in the Tuscan Countryside. Before a final celebratory dinner in the most famous city in Tuscany.

Day 6 - Return to UK - Easy breakfast. Short transfer to Pisa Airport for return to UK.


Route Map


We shall use good quality middle range hotels, with shower and toilet facilities each evening (en-suite) - but always clean, comfortable and full of character. The itinerary is organised on a B&B basis.


What is a Level 3.5 Cycling Challenge Like?

These challenge rides are either longer, with more ascent, or span several days. In the case of single day events, you can expect up to 10 hours cycling. In the case of a multi day ride, you can expect lower daily durations - but of course - the effort is sustained over a longer period. You need to be a keen cyclist for these events, and to enjoy training, and to ride regularly. If the ride is outside the EU, it is likely to be easier in terms of the physical riding, however, you will need to be more resilient - due to more basic living conditions (in the case of Asia / Africa especially)


How Fit Do I need to be to join a Level 3.5 ‘Bike Ride’?

You need to have good endurance for these events. You must be used to doing long rides in the countryside - 6 hours + . You should be doing regular exercise - with some serious cycle training. Your typical comfortable cycling speed will be at least 22-24 km/hr, and you should be able to cycle at high speed for up to 1 hour or 25 km. You may also be concentrating on 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.


Special Notes

Typically evening meals are taken together (not included). Lunches may be organised as picnic, or taken in cafes, subject to weather, and group preferences.


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

Kit lists specific to your trip dates and location will be issued upon enquiry...below is our guide advice to give an idea of what you should bring on a multi--day ride in Europe

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  Clothing
Padded Lycra Cycling Shorts, Cotton Shorts, or Long Cycling Trousers (Tights/Tracksuit Bottoms)
Short Sleeve Cycling T-Shirts (wicking type material) or Cycle Top with rear pockets
Cycling Shoes (approach shoes or sturdy traners suitable), 

Spare Shoes/Sandals for after ride

Casual Evening Wear - tracksuits, jeans, T shirts, fleece ...

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, chargers, EU plug adaptor, 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. It is advisable to check that your travel insurance covers the value of any expensive items of kit that you chose to bring along with you. 

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!


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

To Reserve Your Space on this Challenge

You should fill in the Google Form - linked here below, and then please call us on 01823 444 246 to advise of your payment method. We can accept card payments over the phone, or Bank Transfer. Please note that your space is not confirmed until you have received your booking receipt.

CLICK HERE: Adventure Cafe Challenge Booking Form - For Challenge Events



Guide price

£Price on enquiry



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

Event Location

Giro Tuscany Picture 2
Giro Tuscany Picture 2

Giro Tuscany Picture 3
Giro Tuscany Picture 3

Our Challengers Said...
The trip was great and I thoroughly enjoyed it. Thank you. You’ll be seeing me again!
John   11-Oct-2016
I would like to say how much we all appreciated the amount of hard work and diligence
Jami   07-Sep-2017