Tour of Tuscany 4 Day Cycle Picture 1
Tour of Tuscany 4 Day Cycle Picture 1

Next departure:  Please Call for Details

Best Time of Year: March - October

Max alt:  900m

Dist:  420km

Min age:  18

Duration:  3

Tour of Tuscany 4 Day Cycle

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 scenic hills, and coastal riding - get ready for an all in awesome adventure! Oh and of course - don't forget the wonderful Italian food, wine and hospitality!


We’ll greet you at Tuscany Airport, Pisa. Whisking you off to one of our favourite Pisan hotels to set up our bikes before dining out in old town Pisa.


Our first ride to Florence will head via a café upon the historic city walls of Lucca. We’ll stay outside of Florence centre with easy links to explore the renaissance city and our favourite restaurants near to The Duomo.


Grapevines will line our route through the Chianti region delivering us to the hilltop city Siena. Tonight we’ll dine in the Piazza del Campo the vibrant heart of the city.


San Gimignano the world heritage site will host us for our next

awe-inspiring  coffee stop, before we continue to the hilltop town of Volterra for our final night.


We’ll finish our ride with a blast back over the hills and down into Pisa for evening return flights or an extra night.





Pisa – Florence (D1)

We’ll pause for a photo by the Leaning Tower as we ride towards Lucca, for a coffee stop on the city wall. Our ride towards lunch near to Da Vinci is relatively flat. Although we will have a nice climb afterwards of about 350metres before descending to the outskirts of Florence for our evening hotel. We’ll take a tram to the city centre for dinner & exploration.


Approx 110km / 1000m+


Florence – Sienna (D2)

Our ride becomes more lumpy as we escape Florence via the Piazza di Michelangelo and enter the Chianti wine region. We’ll make stops for coffee and food before exiting the countryside into the picturesque city of Sienna. We’ll stay within walking distance of the central Piazza del Campo, where we will dine in style.


Approx 110km / 1700m+



Volterra – Pisa (D4) 4day


We’ll descend from our accommodation towards Pisa, beginning on quiet roads before reaching increased traffic nearer Pisa as we come into the city along the River Arno. The day has a downhill trend and an option for an additional climb to Castagno Val d’Elsa if you’ve still got it in your legs. Flights can be arranged for the evening (after 7pm) or you can choose to stay an additional evening in Pisa


Approx 95km / 800m+

Siena – Volterra (D3) 4day

We’ll exit the cobbled streets of Siena and onto a fantastically quiet road before heading towards the World Heritage city of San Gimignano for an early lunch. From here we’ll wind our way up and down some more Tuscan hills to the hilltop fortress of Volterra.

Approx 105km / 2000m+





Route Map


We shall use simple hotels, with shower and toilet facilities each evening (sometimes shared, sometimes en-suite) - but always clean, comfortable and full of character. 


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

Pre event Planning & Communications

Inbound Pisa Airport Transfer

  (based on recommended flight times)


4 Nights Hotel Accommodation

  (Twin Share breakfast included)

  Pisa, Florence, Siena, Volterra 

Support Vehicle & Driver


Ride Leader


Ride Snacks

  (Bananas & Bars)


Pisa Return Airport Transfer

  (based on recommended flight times


Excluded From Trip


Excluded / Optional Extra


Single Room Supplement

  (Estimate £290)


Bike Hire

  (Local Pisa Hire)



  (Picnic Style or café set menu)



  (Set Menu)


Extra Night Pisa
Bike Transfer (UK – Pisa)



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



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 swealtering! 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 application



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

Event Location

Tour of Tuscany 4 Day Cycle Picture 2
Tour of Tuscany 4 Day Cycle Picture 2

Tour of Tuscany 4 Day Cycle Picture 3
Tour of Tuscany 4 Day Cycle Picture 3