+44 (0)800 002 9559 / +44 (0)1273 413489 info@bikeadventures.co.uk


Tour of Tuscany Challenge – 2021/22


TOUR REF: TT214 / TT224
TYPE: Road Cycling
LEVEL: Strenuous
17 May – 23 May 2021
16 May – 22 May 2022
DURATION: 6 days / 5 nights (5 days cycling)

    Reset options
    • 150 £
    • 65 £
    • 65 £

Tour of Tuscany Challenge

A more compact version of our classic tour through the Tuscan countryside, starting and ending in Pisa.

Tuscany is known for its landscapes, traditions, history, artistic legacy and its influence on high culture. What better way to experience this than from the saddle of a bike; and of course the Italians love cycling so you will be assured a warm welcome wherever you stop.

This wonderful trip has previously run with 7 riding days but has now been repackaged to fit with a 1 week holiday inclusive of travel.

We start our ride from the iconic city of Pisa we stay within walking distance of the obvious star attraction.

Our first day is spent on the coast before turning inland to complete a very approximate circle taking in the very best that Tuscany has to offer. The route passes through central Florence, using cycle paths wherever possible, and even cross the famous Ponte Vecchio.

We eventually return to Pisa from the north east, following a traffic-free cycle path along the river.

Tuscany can be very hilly, and there are certainly hills on the route – indeed there are a couple of quite challenging days on this tour – but the route offers a real mix of riding with several quite flat days. The longest day is 81 miles and the daily average is 76.

This is a hotel-based trip using mostly 3* hotels.

There’s also our Pisa to Sicily trip. So why not take a 3 week break and REALLY see Italy?


I really enjoyed the trip… scenery was spectacular with some brilliant descents on great roads… Have done 4 trips with Bike Adventures now, USA will be my 5th. I keep coming back, so something must be attracting me!

Lynn R

If you would like to read other people’s comments on our holidays then check out the Customer Comments page.


Day 0 – Arrive in Pisa

We will meet you from the airport. Depending on the arrival time you may want us to relieve you of your bike and/or luggage so you can explore the city. We stay in central Pisa.

Day 1 – Pisa to Castiglione della Pescaia – 81 miles

A mostly flat coastal ride. Leaving Pisa, the route follows the Mediterranean coast through several seaside towns to Follonica, then climbs over a headland to Castiglione della Pescaia . An easy introduction to the tour, with plenty of cafes and bars along the way.

Day 2 – Castiglione della Pescaia to Castiglione d’Orcia – 69 Miles

The route briefly follows the coast before turning inland to cycle through Tuscany’s rolling countryside.

Day 3 – Castiglione d’Orcia to Terranouva B – 78 Miles

A day of mixed riding with the reward of some fantastic scenery. We cycle through the rolling hills and vineyards of Tuscany via the beautiful historic hill-top town (the clue is in the description!!) of Montepulciano, famous for its wine and Pecorino cheese. After this things become easier along a valley through sunflower fields and olive trees, following a canal to provide a glorious, relaxing cycling experience.

Day 4 – Terranouva B to San Miniato – 74 miles

‘The day we go to Florence’. The roads are inevitably busy on the approach to the city but the route follows cycle paths where possible, climbing to the famous Michelangelo square with spectacular views over Florence, before descending to cross over the Ponte Vecchio to follow a traffic-free cycle path alongside the River Arno out of the city.

Day 5 – Florence to Montecatini – 79 Miles

A gentle ride to the fantastic walled town of Lucca before climbing round the side of Monte Pisani to descend down to the city of Pisa. Here, a traffic free cycle path alongside through the river takes us safely through into city. The ride finishes back in central Pisa.

Day 6 – Transfer to Pisa airport for the journey home.


Holiday Details:

The Country: Italy offers an incredible welcome to those on 2 wheels and, despite many assumptions to the contrary, drivers are very considerate of cyclists outside of the big cities.  Of course, the climate and cuisine are perfect for those seeing the country by bicycle, and the Italians are always keen to strike up conversation regardless of the linguistic limitations of either party.

The Tour: This is a Fully Supported Cycling Holiday with a leader/mechanic, and support vehicle to carry all the luggage and provide any necessary assistance. The holiday is designed to take you through the great variety of scenery that Tuscany has to offer. The total distance is just under 400 miles, with an average of about 55 per day. There are no rest days.

The first part of the tour is very easy cycling along the Tuscan coast.  Coastal roads inevitably, carry more traffic and pass through more towns than some of our other routes.  However, the going is never unpleasant and with the advantage that you are never far from a shady cafe where you can enjoy a coffee or gelato. 

Once we turn inland the route becomes hillier and there is one very hilly day but the daily mileages have been adjusted to make the hilliest days also the shortest.   Despite the hills there are several flat or partly flat days where we make use river valleys and cycle paths.

Accommodation & Food: This is a hotel-based trip, accommodation will generally be graded 3* – 4* or similar, offering clean and comfortable rooms. Single people travelling alone will be booked into a twin bedded room with another person of the same sex – unless the additional single supplement has been paid. We book rooms with en-suite facilities where available, but this cannot always be guaranteed. Breakfast is provided at the accommodation, most hotels also have a restaurant attached for an evening meal, or there is at least one other restaurant nearby. Note that Italian breakfast is often minimal, sometimes little more that coffee and pastries.

Start/Finish: The holiday starts and ends in Pisa and we will collect guests for the airport transfers. Flights to Pisa are currently operated by British Airways, Ryanair and Easyjet from London, Ryanair from Nottingham and Jet2 from Manchester.  Note: The cost flights is not included in the price of the holiday. You must book flights yourself (or make your own alternative arrangements).

Cycle Transport:  If required, and for an additional fee, we can also arrange for your cycle to be transported to and/or from Pisa to anywhere in the UK.

Documents: You require a passport to visit Italy. Nationals of some other countries also require a Visa. Non EU passport holders should check with the nearest Italian Embassy. You are also required to have travel insurance for the duration of the holiday and you will be required to provide evidence of a suitable travel insurance policy.

Bikes: All types of cycle are suitable for the trip. The most important thing is that the bike functions properly and that you are comfortable riding it. However you should make sure that your bike has suitable gears as parts of the route are hilly, with some quite long climbs. Most people will require a cycle with a triple chainset. If you are riding a mountain bike then you should fit it with narrow ‘slick’ tyres. You should also make sure that you are able to carry some spare food and clothing with you on the bike.

Tour Price includes:

Hotel accommodation
Vehicle support
Services of leader/mechanic
Local transfers
Route information
Certificate for those that complete the trip

Tour Price does not include:

Lunches or evening meals
Snacks or drinks required during the day
Travel to/from Pisa
Cost of any optional excursions, entrance fees etc.

Get In Touch

If you have any questions about any of our trips, please call us on 0800 002 9559 or send us a message below.