Giro Tuscany Compact Ride Picture 1
Giro Tuscany Compact Ride Picture 1

Next departure:  Please Call for Details

Best Time of Year: March - October

Max alt:  700m

Dist:  331 km

Min age:  18

Duration:  4

Giro Tuscany Ride: Lucca, Florence, Siena & Pisa

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 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. This itinerary offers a few different options, enabling us to cater to the style of riding that your group wants to do. See the 'Itinerary' section below for a couple of different options.

The first day of riding sees us take in the cultural centre of Lucca before finishing in the home of the rennaisence itself, Florence. We then pass on through the edge of the Appenine Mountains, through Reggello, and the famous hill top towns of Castellina in Chianti and Radda in Chianti. We'll be spending the night in the incredible city of Siena before heading back to Pisa through San Gimingnano and yet more stunning towns, villages, and hillsides. 



Day 1: Pisa > Lucca > Florence

Option One: 97km / +800m

A perfect warm-up day and introduction to Tuscany. We'll see historic cities and towns, gorgeous rivers and forests, and of course classic Italian coffees and ice creams! You will then have the evening to explore this incredible city.

Option Two: 112km / +1000m

Both options climb over a ridge on the way into Florence, but Option Two takes a longer and higher route through this line of hills. From the top, on a clear day, you can see all the way back to our departure point of Pisa!

Day 2: Florence > Montevarchi > Gaiole in Chianti > Siena

Option One: 109km / +1550m

We begin our second day of riding with a gentle warm-up along the valley before climbing up into the hills. We then have a stunning balcony ride high above the valley before arriving into Reggello. We'll then swoop down to Montevarchi before climbing up into the hills again. We then have a stunning ride up through Chianti countryside and historic hilltop village after historic hilltop village. Tonight is spent in Siena, yet another world-famous cultural centre.

Option Two: 103km / +1300m

We set off along the valley, but instead of branching up into the hills towards Reggello, we stay low in the valley, rolling through riverside villages to Montevarchi, where we rejoin Option One. We then have a long steady climb up into the hills before a stunning ride up through Chianti countryside and historic hilltop village after historic hilltop village. Tonight is spent in Siena, yet another world-famous cultural centre.

Day 3: Siena > San Gimignano > Pisa

Option One: 112km / +950m

The final day of riding sees us taking in the edge of the Tuscan hills, containing maybe the prettiest villages so far! We'll eventually sweep down out of the hills, and follow the river back into Pisa, for a well-earned celebratory dinner!

Option Two: 132km / +1300m

The extended final day has us drop down out of the hills early to the stunning village of Castelfiorentino, before a tough climb back up to join Option One's route and the long descent down to our finish in Pisa.


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 twin-sharing 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.




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

- Cycle leader(s) (experienced with first aid qualification)

- Support Vehicle back-up with driver/mechanic

- Transfers for bikes to and from airport

- Accommodation

- Breakfasts 


Excluded From Trip

- Evening meals

- Transport to/from Pisa

- Lunches


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. Please listen carefully to all instructions from your 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 Compact Ride Picture 2
Giro Tuscany Compact Ride Picture 2

Giro Tuscany Compact Ride Picture 3
Giro Tuscany Compact Ride Picture 3