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Pisa to Sicily

Pisa to Sicily (Challenge) – 2022/23


TYPE: Road Cycling
LEVEL: Strenuous
03 Sept – 13 Sept 2022
02 Sept – 12 Sept 2023

11 days / 10 nights (9 days cycling)
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    Optional extras

    • 385 £
    • 70 £
    • 70 £

Pisa to Sicily – 9 Day Challenge

Our popular Italian classic repackaged for those looking for more challenging riding. A sensational ride down the Mediterranean coast of Italy from the iconic leaning tower, finishing with a day in Sicily. 

For some riders a day just isn’t worth doing unless the mileage nudges 3 figures (miles!) and this trip is designed for them. Our tried and tested classic Italian route but repackaged for 9 days riding.

Guest must make their own way to Pisa Airport, from where we will provide transport to our accommodation. Our route immediately takes us on the coastal road before heading inland to enjoy the beautiful Tuscan fields and villas. As we approach Rome we pass Lake Bracciano before squeezing past the city for a night just south of Fiumicino.

Once south of Rome we follow the coast road before once again before heading inland to skirt the bustling sprawl of Naples, stopping the night in Pompeii. We must then climb over the hills to Amalfi and follow the stunning Amalfi coast. The descent into Amalfi must rate as one the greatest switchbacks anywhere in the world and an incredible ride!  

Eventually the terrain becomes flatter with many tunnels and viaducts to ease the way as we head down to the foot of Italy, before boarding a ferry for the short crossing to Messina and a final day of riding along the southern Sicilian coast to Catania from where, after a good night’s rest, we fly home.

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. Our hotel and campsite are in Marina Di Pisa, a few miles away.

Day 1 – Pisa to Grosseto – 95 miles
We immediately pick up the coast road, first passing through the busy resort town of Livorno, after which the route becomes quieter with occasional small towns. Towards the end of the day we briefly head inland to cross a small headland, arriving in the resort town of Follonica. We follow a cycle path along the seafront through Follonica before veering inland across another headland through open Tuscan farmland then through shady woods as we return to the coast.  We then follow a canal path inland to skirt the busy town of Grosseto. 

Day 2 – Grosseto to Tarquinia – 95 Miles
We start by heading into gently rolling Tuscan hills with pretty villas and picture postcard hill-top villages. After passing the ‘near island’ medieval town of Orbetello the rest of the day is slightly hillier, spent mostly inland to avoid the busy coastal highway. We climb for lunch in the hill-top town of Capalbio before many miles of open countryside, bypassing Montalto di Castro before arriving at another medieval resting spot – Tarquinia.

Day 3 – Tarquina to Lido Di Ostia – 80 miles
They say all roads lead to Rome but many are busy and make for unpleasant cycling. We offer much quieter roads as we skirt Rome. We first head inland to clip Lago di Bracciano before returning to the coast to squeeze between Leonardo da Vinci airport and the sea. We pass through Fiuminino then take a minor bridge across the Tiber, passing, close to the ancient roman port of Ostia finishing in Lido di Ostia.

Day 4 – Lido di Ostia to Formia – 95 miles
A return to costal riding on the quieter roads with one brief foray inland to sneak behind Anzio and Nettuno. The  riding is easy as we ride many miles of causeway across the marshy coastal flats.  Later we pass inland behind San Felice Circeo to the busy port of Terracina. We then head inland via Fondi for some variety (and a few hills) as well as to avoid the busy coastal road and some hairy tunnels!  We rejoin the coast in Formia.

Day 5 – Formia to Pompeii – 80 miles
Ask anyone who has visited Naples and they will tell you it is a fascinating place…just do NOT cycle there!  Our day is spent getting past this major sprawling coastal population centre.  Inevitably it is not the quietest day’s cycling but our route exploits every possible minor road as we work our way past the city. The first part of the day passes through relatively few towns before we thread our way between Caserta and Naples, while also avoiding the many major roads and motorways that serve these communities. Once past Naples we approach Vesuvius from the north and skirt the edge of the Volcano all the way to Pompeii where we spend the night.

Day 6 – Pompei to Marina Di Ascea – 95 Miles
A very hilly day. We are quickly out of Pompei and immediately head inland to climb over the hills to Amalfi, missing the very hilly coastal route via Sorrento. There is a stiff climb of some 6 miles but the reward is a sensational plunge down to Amalfi; probably one of the most spectacular coastal switchbacks in the world. From Amalfi the coast road continues to be lumpy before eventually flattening out for the last few miles through Salerno. The miles are easy as we head along the coast through the archaeological sites around Paestum, then the road begins to rise and fall again as we pass Santa Maria di Castellabate. Our night is spent in Marina di Ascea; if you get in early why not climb the hill to see the roman tower and amphitheatre? 

Day 7 – Marina Di Ascea to Fuscaldo- 105 Miles
A long day which starts with some stiff climbs but the stunning coastal road offers plenty of compensation for the effort! The road flattens for the rest of the morning then, after  a lunch break in Marina di Camerota there is more climbing to be done as the road turns inland before rejoining the coast for a run in to Sapri and on to Scalea. The views today are amongst the best of the trip. We now enter an area where the application of money and heavy engineering has resolved the problem of hills. For many miles we ride on bridges and through tunnels and the route is reasonably flat, though still very pretty. We follow the coast all day, occasionally leaving the coastal highway to exploit quieter roads through seaside towns or along seafronts.

Day 8 – Fuscaldo to Bagnara Calabra – 110 miles
A long day but easy day. Our route now hugs the coast for the remainder of the trip as we follow S18, detouring onto quieter roads wherever possible. We finish in Bagnara Calabra, just short of the Toe.

Day 9 – Bagnara Calabra to Catania- 75 miles
Our first 12 miles are spent getting to the ferry port of Villa San Giovani from where we make the short crossing to Messina. We then enjoy a brief taste of riding with the sea to the left for a change as we ride west, skirting Mount Etna, to arrive at Catania.

Day 10 – Depart Catania
Catania airport is just a short transfer from the hotel.


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 Pisa/from Catania
Cost of any optional excursions, entrance fees etc.



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, and support vehicle to carry all the luggage and provide any necessary assistance. The holiday is designed to offer you the challenge of riding a substantial part of the length of Italy, while at the same time taking you through the great variety of scenery that Italy has to offer. The distance from Pisa to the toe is about 800 miles, to which we add another 60 to finish in Catania on the island of Sicily. The first part of the ride is through rolling countryside with few short steep climbs. The area between Pisa and Rome is mostly fairly flat to rolling, becoming hillier as we skirt Rome. The second week takes us along the Amalfi coast where the terrain is rugged with some long climbs and descents, but most of these are well graded and should not provide too much of a problem to regular cyclists. The last few days are flatter thanks to the numerous viaducts and tunnels, though there are still a good number of gentler climbs. The central spine of Italy is mountainous and the few roads that cross this spine are very hilly.

Our route follows the coastal roads which, 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. The average daily distance is 60 miles, and there is one rest day in Pompei.

Accommodation & Food: This holiday has the option of camping or hotel accommodation. If you are camping you will be staying at established campsites, with hot showers etc. You will need to provide your own tent, sleeping pad and sleeping bag, although tents can be hired from us if required. Buffet style continental breakfast is provided at the campsite each morning. If you choose an 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: The holiday starts in Pisa and we will collect guests from the airport for transfer to the hotel/campsite. Flights to Pisa are currently operated by British Airways, Ryanair and Easyjet from London, Ryanair from Nottingham and Jet2 from Manchester. Note: The cost of the outbound flight is not included in the price of the holiday. You must book the flight yourself (or make your own alternative arrangements).

Finish: The holiday ends in Catania on the island of Sicily. Direct flights are currently available to London Gatwick with British Airways or Easyjet. Alternatively, flights to most UK airports are available via Rome or Milan. Transport will be provided to Catania airport. Note: The cost of the return flight is not included in the price of the holiday. You must book the flight 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 the start at Pisa and/or to return your bike from Catannia 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, particularly along the Amalfi coast, 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

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.