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The Italian Coast to Coast 

Day: 1  2  3  4  5  6

See Italy like you've never seen it before.

Here is the latest creation of Cycle Friendly – a revised Coast to Coast ride in just 4 cycle days which takes in many iconic sites of Northern Italy as it passes through the heart of Tuscany, over the Apennines and into Emilia Romagna and by San Marino. 

At the end of each cycling day we shall stay in delightful 3* hotels and one 4* which has swimming and spa facilities. Lunches will be either our famous picnics or selected restaurants in great settings.

The ride ends at the beach where hopefully there will be some time to chill out , enjoy a celebration meal before flying back to the UK.

Essential Information

Date: 10th-15th May 2022
Price: £1375
Duration: 6 Days 5 Nights
Hotels: 3*/4* in country locations 

The Route

The route is 210 miles long with an elevation gain of 19,600 ft, an average of  52 miles and elevation gain of 4,900 per day.

It starts at Cecina, a seaside town on the Med just 40 miles south of Pisa, is full of variety , following the plains from the Med, river valleys , several dramatic passes over the Apennines and up to several hilltop towns and cities which are a distinctive feature of the region. 

These include Volterra, San Gimignano, Castellina and Radda in Chianti, San Leo and San Marino.

The Itinerary


Day One

Relax on the Beach

We fly into Pisa and transfer to Cecina to the South, just under 40 miles in 45 minutes. Unpack and fit bikes ready for the following day. 

Depending on arrival time, you may be able to relax on the beach. 

We will stay in Hotel Tornese.

Hotel Tornese

Day One

Day Two

Cycling Distance: 50 Miles

A further drop back to 600 ft (27mls) brings us to another 1000 ft climb to the splendid hill city of Volterra at 1580ft (32.5mls) for lunch and a city tour.

Exploring Volterra

We start cycling by the sea at Marina di Cecina. Once out of the town, with 10 miles along country lanes we climb gently to 850 ft and reach Guardistallo. We drop back down to the river and reach the main road at Ponteginori. A mile further, we turn left, and follow the picturesque road to Montecatini di Cecina at 1280ft , a climb of 1000ft (24mls).

A Morning of Climbs

We now descend through Montebradini (34mls) to the river at just 400ft (38mls) and yet another and final 1000ft climb through Vicarello brings us to Castagno at 1500ft (44mls). Then it’s a slight drop for the grand view of San Gimignano which we reach after 50 glorious miles and 4 climbs. Here we will stay night in a good quality hotel and savour the unusual sights of the town in the evening.

Final Climbs to a Grand View

Hotel La Cappuccina

Day Two

Day Three

San Gimignano to Florence

Cycling Distance: 46 Miles

This is a delightful day of cycling, not too far and with moderate hills. It’s also one of striking contrasts. We leave San Gimignano on a gentle downhill into the valley of Elsa and soon enter Poggibonsi (7mls). This is an industrial town which we will quickly cycle through. On the other side of course we start to climb again into Chianti Country. Of course Chianti is the quintessential countryside of Tuscany and this route up to the pretty town of Castellina (18mls) at 1800ft. Here you will be rewarded with a welcome coffee stop.

Through Poggibonsi to Chianti

Then its onwards towards Florence with a modest climb of 450ft to Impruneta (38mls) after which the Chianti countryside recedes and the hills of Florence can be seen. We will stay on the South side of the River Arno but within easy reach of the centre of the City

Heading Towards Florence

Then its onwards on the Chianti road through vineyards, villages and sweeping countryside giving ever changing views with one further hill climb –approx 550ft – to Greve in Chianti – a delightful town and the main centre at just under 30 miles.

Here we will have lunch in one of the many restaurants in the square.

Beautiful Chianti Countryside

Classic Hotel

Day Three

Day Four

Florence to Stia

Cycling Distance: 38 Miles

Soon after Rufina (18mls) we leave the valley and commence the climb of the day to the top of the pass at just over 3000ft. We will have a picnic lunch soon after we start the climb at about 25 miles out.

A Scenic Lunch

Another day of contrasts starting with a cycling tour of Florence and of course the opportunity for a coffee stop in one of the main squares and even a quick peep into the cathedral or museum. The route out of Florence follows the river westwards with the Apennines beckoning. The first 20 miles of the day is virtually flat and once out of Florence is an opportunity for some fast cycling.

Fast Cycling from Florence

Albergo Falterona

Then it’s to the top of the pass (34 mls) and a coffee stop in the valley below before entering the town of Stia in the foothills of the Apennines where we will stay the night.

Entering Stia

Day Four

This is the day when we cross the Apennines into Emilia Romagne. This involves the climbing of three passes on small mountain roads in quick succession, the highest being 4100ft from a base at Stia of around 1500ft. Luckily the drop between passes is relatively small, the maximum being 1000ft. On leaving Tuscany we drop into the delightful valley containing the alpine resort of Bagno in Romagna - here we shall have our lunch –yes the 3 passes are your morning exercise only – and by Bagno you would have covered just 27 of the day’s 61 miles.

Mountain Roads to Bagno

From Mont Fornaoilo it is almost a 20 mile continuous downhill to complete a glorious day finishing at a small hotel just to the south of the town of Novafeltra at just 1000ft.

Downhill to the Hotel

Day Five

Stia to Novafeltra

Cycling Distance: 62 Miles

After lunch we leave the valley and the relatively main road to rejoin roads climbing gently up and up passing beautiful upland but remote villages with some respite at Alfero (36mls). Then the final climb of the day takes us south to Monte Fornaiolo (41mls) at 4.400ft, the highest point of the C2C and from where there are stunning views across the Apennines. You should be able to see Monte Carpegna which features regularly in the Tour d’Italia.

The Highest Point of the C2C

Falcon Hotel

Day Five

Day Six

Novafeltra to Riccione

Cycling Distance: 58 Miles

From San Leo , we descend once again to below 1000ft with ever closing views of San Marino, perched on a massive outcrop which dwarfs San Leo. This is our objective – and culminates in a steep climb up zigzags on the face of the rocky promontory. San Marino at 21 miles and 2000ft is an ideal place for an early lunch and some time to explore the independent state on foot for a couple of hours.

A Beautiful Climb to San Marino

Hotel Poker

The finale day commences once again on minor roads climbing to 2500ft – the highest point in the area and with good views of San Leo to the north. A gentle descent takes us to San Leo (7 mls), an historic town perched on top of a rocky outcrop. This is an ideal morning coffee stop.

Riding to San Leo

The final 16 miles is virtually all downhill to the sea and the last few miles leaving the hills for the suburbs of Rimini and Riccione. Our destination is the Hotel Poker – a comfortable 3* hotel with pool. We expect to arrive at 4pm. After putting bikes away, you can have a dip in the sea and then have a fabulous celebration meal.

A Celebration Meal

Day Six


Who is this ride suited to?


The Ride is suited to proficient cyclists who cycle regularly or have trained for several months. You should be able to ride 30 to 35 miles on road in half a day. Particularly suited to singles and couples. All ages are welcome.

What's the terrain like?

A variety of roads – some main some country with visits to severel iconic towns and cities including Florence. Many hills some substantial especially over the Apppenines. Open views most of the way create great distractions from the climbs. Some really long and wonderful downhills.

What's included in the price?

Accommodation; all meals and snacks including picnic lunches; transfers by road; maps and route notes; hired bikes.

What's not included?

International Flights to Pisa and returning from Bologna,Rimini or Ancona, personal insurance, personal incidentals inc. drinks; tips.

Is there a support team?

Yes. This tour is fully escorted with Tour manager, Lead cyclist, cycle maintenance and first aid, provision of picnic lunches.

What's the weather like?

Temperatures generally between 20 and 25 degrees C – however , warm clothing possibly required for mountain passes up to 4,500ft

What about flights?

Riders to arrange their own flights to Pisa from whence transfers to the start at Cecina will be arranged, and return flight from Rimini, Ancona or Bologna. Advice on flights will be provided.

Is there a luggage restriction?

Please refer to your airline for any restrictions.

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