Italia Grand Tour Cycling Expedition

A 19 days Road Bike Adventure across Italy.

What’s the meaning of “Grand Tour”? The word “tour” can be translated in Italian as “Giro”.

An innovative way of travelling started to be popular in Europe in the late sixteenth century and became a trend of “trip to Italy”. The “Giro” soon became a fad, recognized with an international wording: The Grand Tour.

With the Grand Tour, the trip was proposed itself as the sole and only purpose, and from that moment travelling turned into tourism; in the name of learning and knowledge on one side and the pleasure of evasion and pure fun on the other. The Grand Tour has established itself as a real institution.

The trips to Italy gave a new impulse to literature, painting, and to all the remarkable art of the XII and XIII Centuries.

With this spirit we have designed a cycling holiday all along Italy. Italy is beautiful, there are no doubts, but is even better seen from the bike.

It is a very cycling challenge holiday, 16 days cycling.

The Pianura Padana plains and the river Po, from the lagoon and river mouths we move inland to visit great city centers. Before cross the Apennines from the Adriatic side toward the Tyrrhenian sea side we ride the hills of Emilia, the kingdom of the Italian food excellence. The first Apennines pass bring us to Fiesole, just the best spot to admire Florence. We enjoy to ride again on the hills of Tuscany and Umbria before to go on the Apennines again. La Strada Dei Sette Ponti, Cortona, Lago Trasimeno, Todi and Tevere valley.

After these, we are ready to climb and admire The Gran Sasso Mountain range, the king of the Apennines. Then Santo Stefano di Sessanio, the Majella National Park. From the Apeninnes we reach the Adriatic sea by Molise clay hills. Gargano limestone promontory offers great ride’s routes and typical fishing villages. From here we entry in Puglia, all the way to the south east cape via Castel del Monte, Altamura, Matera, Alberobello, Ostuni, Lecce, Otranto and finally Finis Terrae.

Booking Enquiries


UNESCO World Heritage: Venice, Ferrara, Florence, Castel del Monte, Matera, Alberobello.

Parks: Po river delta, Parco di Argenta, Parco del Gran Sasso, Parco della Majella, Parco del Gargano.

Great city center: Cortona, Castiglione del Lago, Città della Pieve, Monteleone, Todi, Amelia, Rieti, Santo Stefano di Sessanio, Pescocostanzo, Termoli, Peschici, Vieste, Altamura, Ostuni, Otranto, Lecce.

Great spot to ride: The lagoon and Po River, the Bolognesi Hills, Appennine passes, Tuscany country side, La Strada dei 7 Ponti, Trasimeno Lake, Umbria hills, Molise hills, Gargano promontory, Olive fields, The Salento coast.

Tour Information

Price –  € 4.300,00

Single Room Supplement – € 450,00

Accommodation 4 star hotels / boutique hotels

When –  30th May to 17th June

Catergory Road Cycling Holiday

Grade – C  (Read our Grades of Difficulty)

Start / End – Venezia/ Santa Maria di Leuca

Suggested Airports Start / End – Verona / Bari

Duration – 19 Days

Days Riding – 16 Days

Terrain Hilly and Mountainous

Kind of Tour – Point to Point

Guided Tour One cycling guide every 8 riders and another guide driving the support vehicle

Support Vehicle We always have a van supporting the group.

What’s Included

  • 18 nights in 3 and 4 Stars Hotels
  • 8 pic-nic lunches, 6 lunches at resturant, 7 dinners
  • Full tour service including 2/3 guides with deep knowledge of the area, skilled and equipped with any indispensable tools to ensure the safety of the group
  • Support Vehicle. Luggage transportation all along the tour and the scheduled stages. Bike mechanic assistance. Refreshments during the rides
  • All guides qualified in First Aid
  • Airport collections / drop-offs from local airport on scheduled arrival and departure days
  • Stretching and yoga classes at the end of the ride

What’s Not Included

  • Personal clothing and equipment
  • Travel insurance
  • Bar bills, telephone calls, souvenirs, etc.
  • Bike hire (available if required).
  • Flights & charges for travelling with your bike
  • Airport transfers on days other than the scheduled arrival / departure days
  • Laundry services at the accommodations

Italy Grand Tour Itinerary




Chioggia Arrival D
2 Chioggia Visit to Venice B


Ferrara Chioggia to Ferrara Easy 100 km / Hard 140 km  B   L


Colli Bolognesi area Ferrara to Colli Bolognesi Area 125 km / Ascent 1200 mt  B   L  D



Colli Bolognesi to Fiesole

90 km / Ascent 1800 mt B   L
6 Cortona Fiesole to Cortona 125 km / Ascent 1600 mt B   L  D


Todi Cortona to Todi 130 km / Ascent 1800 mt B   L


Rieti Todi to Rieti 115 km / Ascent 1700 mt  B   L
9 Sessanio Santo Stefano Rieti to Sessanio S. Stefano 125 km / Ascent 2300 mt B   L  D


Pescocostanzo Sessanio S. Stefano to Pescocostanzo 130 km / Ascent 2200 mt B   L
11 Bagnoli del Trigno Pescocostanzo to Bagnoli del Trigno

70 km / Ascent 900 mt

B   L  D


Termoli Bagnoli del Trigno to Termoli

90 km / Ascent 1300 mt

B   L


Peschici Termoli to Peschici

135 km / Ascent 1400 mt

B   L


Manfredonia Peschici to Manfredonia

110 km / Ascent 1800 mt

B   L


Altamura Manfredonia to Altamura

130 km / Ascent 1100 mt

B   L


Alberobello Altamura to Alberobello

100 km / Ascent 800 mt



Lecce Alberobello to Lecce

130 km / Ascent 500 mt

B   L  D


Santa Maria di Leuca Lecce to Santa Maria di Leuca

110 km / Ascent 900 mt

B   L   D
19 Departure

Tour Description Day by Day.

Day 1. Arrival.

On your arrival at the airport you will be meet by the local guides team and transferred to your first accommodation, located in the town of Chioggia.

We will set some time aside to learn all about your week of road biking and fit the bikes.

Hotel in Chioggia.

Day 2. Sightseeing in Venice and its lagoon.  Ferry boat from Chioggia.

Venice is an unending source of marvels and admi- ration just because of the way it is: the city has been built on a platform of millions of wooden posts driven into the sand, crossed by dozens of canals thronged with boats and gondolas, woven together by narrow alleys, the “calli”, which are punctuated by opening into marvelous “piazze”, the “campi”. Venice’s lagoon extends from north to south in the shape of a bow, from the mouth of the Sile river to the mouth of the Brenta river, shielded by the islands of the Lido and Pellestrina.

We head for Venice from Chioggia harbor, by the vaporetto (boat buses) which would allow you to stop and cycle along the Lido island and Pellestrina island (bikes can be carried). It takes about 1 hour and 45 minutes to cross the lagoon. The plan is to spend all the morning and the afternoon in Venice and come back to Chioggia for dinner time.

Hotel in Chioggia.

Day 3.  Chioggia to Ferrara.

Easy option 100 km  •  hard option 140 km – All flat

Following minor roads we cross the river Brenta by the bridge in the south of Chioggia. To get to the Po Delta area we must first cross another important river, the Adige, whose Delta marks the end of the Venice lagoon. The Adige estuary is fairly wild still: on one side there is the beach, a recently deposited sandy area, on the other side and inland is the lagoon, near that Porto Levante. Here we need to take a boat to cross the river.

From Porto Levante we head towards Ca’Venier: it is an island enclosed by the Po di Venezia to the south, and by the Po di Maistra to the west and north. Everywhere you look there are impressive images, reflective or poetic, but always inspiring and of great evocative power; the bicycle is the best transport to appreciate these nuances of nature. At this point the route turns onto the Destra del Po Cycle-tourism path, and backroads to be followed to our final destination, all along Po river till Ferrara, a Unesco world heritage city center.

Hotel in Ferrara.

Day 4.  Ferrara to Colli Bolognesi.

Distance 125 km  •  Total Ascent 1200 mt

The first part of the day is still on the Po valley, the main plain of Italy: Pianura Padana. We cross the quiet country side by minor roads, along irrigation channels passing trough Argenta park, till Castel San Pietro Terme. From here we start climbing the clay hills on the east side of Bologna, it offers beautiful views and we can admire the clay formations, called “gessi”. Our accommodation is on the green hills, that lean to the slopes of the Apennine mountains.

Hotel in Colli Bolognesi Area.

Day 5. Colli bolognesi to Fiesole (Firenze).

Distance 90 km  •  Total Ascent 1800 mt.

From Bologna hills we approach our first pass on the Apennines. A long and steady climb to Passo della Raticosa, immersed on dense beech forest. Our mind go to the time when this routes were the main connection between Florence and Bologna. At the pass we deserve a rest and a coffee. Then ready to face a long downhill to Firenzuola and the second Appennine climb to conquer Passo del Giogo. On the way down we pass next to Maranello circuit and we stop for a rest in Borgo San Lorenzo. Borgo means village and from the word ‘Borgo’ came the word ‘borghese’ (bourgeoisie).

The last climb is the easiest of the day, not too long and gentle. The last section, undulating, offers great views of the Arno Valley and Florence. Our hotel is just on the hills outside Florence, overlooking the gem of Renaissance. Unesco world heritage city center.

Hotel in Fiesole.

Day 6. Fiesole to Cortona.

Distance 125 km  •  Total Ascent 1600 mt

We leave Florence to explore Tuscany. A region with unique landscapes, delicious cuisine and even finer wines! Following the banks of the Arno river valley we ride along twisting roads and we could stop to admire past stone-built villages and carry on pedaling through fertile landscapes. We ride warmed by sun, then through oak forest on the slope of the mountains next to the valley, riding into tiny historic towns. By the time, stroke by stroke, we will climb the hills, now in front of our eyes is passing the typical landscape of Tuscany: byways on the ridges lined with cypress trees and vineyards on the slopes. Riding on the Sette Ponti (Seven Bridges) road is really a pleasure, we stop at the Ponte a Buriano, just to admire the rustic backdrop to the Mona Lisa’s enigmatic smile.

The “Sette Ponti” road brings us to Arezzo. Arriving to the town we obviously find the same kind of urbanization that modern civilization is spreading all over the world. But If you can bear to ride for a bit into it, your patience will be rewarded and you will understand that it is worth it. Soon you can discover the old town, a Renaissance pearl. From Arezzo we arrive in Cortona, founded by Etrurians in the VII th century BC, a magic town, just on the top of the hill, with incredible views all around: towards the Tuscany hills, the Apennine Moun- tains and the Trasimeno lake.

Hotel in Cortona.

Day 7. Cortona to Todi.

Distance 130 km  •  Total Ascent 1800 mt

Today we leave Tuscany to ride towards south, crossing the border into Umbria, the “Green Heart of Italy”. We ride along the Lago Trasimeno and its deep-blue waters. Here took place the epic clash of Hannibal and his elephants with the Roman legions. We can visit the medieval village of Castiglione del Lago. From the lake we go on the Mountains of Val di Chiana. The mountains are covered by olive trees and dense oak forests. Cycling by quiet minor roads we arrive to enchan- ting medieval villages, rocked on the top of the hills, as Città della Pieve. We carry on on the ridge of the Monte Peglia  and from here down to Todi, one of the most beautiful medieval cities in Italy, perched on a hill and overlooking the Tiber valley.

Hotel in Todi.

Day 8. Todi to Rieti.

Distance 115 km  •  Total Ascent 1700 mt

The first part of our ride, through gentle rolling hill, bright and colorful, take us to Amelia. The town lays on the top of a rocky hill on whose land, olive and ilex trees grow all around, only interrupted by the river Tiber. The histoy of Amelia is as old as legend is. The enormous town walls date the VI century B.C. Beside the town walls, several cisterns and roman houses testify the importance of Amelia during the Caesar empire. This whole area is characterized by a harmonious succession of landscapes that seem authentic natural frescoes. A plunge into the valley and a jump up the hill lead us towards Narni.

We are entering the Lazio region, the landscape will always keep the charm of an unspoilt nature characterized by green hills and small medieval towns perched on top, as Cottanello. Just one more climb and another pass, 8 km long, to reach 840 meters asl, and we could go down the valley heading to Rieti. The town centre rests on a small hil- ltop, overlooking a wide plain at the southern edge of an ancient lake. The area is now the fertile basin of the Velino River. Rieti is a quiet town with a lot of interesting sites. A part of the town is still surrounded by the town walls with characteristic round and square towers and 5 town gates. The WWF has created a trail along the river, it allows visitors to admire some of the most beautiful cor- ners of Rieti, surrounded by greenery.

You can wander around the streets of this splendid town and enjoy a tasty dinner in one of the many characteristic local restaurants.

Hotel in Rieti.

Day 9.  Rieti to Sessanio Santo Stefano.

Distance 125 km  •  Total Ascent 2300 mt

We climb today the King of the Apennines moun- tains, the “Gran Sasso” (The big rock). May be the hardest stage of the tour, today we climb three mountain passes. The first pass at 1000 m asl, the second at 1600 m asl and the last one, Campo Impe- ratore,  at 2100 m asl. Here in 1999, Pantani dressed the pink jersey and actually won his Giro. From Assergi are 31 km with an average gradient of 5%, maxi- mum slope 10%. This magic place is part of the Giro d’Italia history and a panel on the top reminds Panta- ni’s time record. From the Gran Sasso, after a section on a plateau with a moonscape, we embark in a thrilling downhill till the unique village of Sessanio Santo Stefano, a magic place!

Hotel in Sessanio Santo Stefano.

Day 10.  Sessanio Santo Stefano to Pescocostanzo.

Distance 130 km  •  Total Ascent 2200 mt

Another day riding along the Appennines mountain, trough Parco della Majella and night on the high plateau, in the beautiful medieval town of Pescocostanzo. The Majella Park is renowed for its wildlife, expecially the wolfs and bears, the vast plateaus of high altitude and wild and impressive canyons, but also the Park of the hermitages, the Abbeys, the dry stone huts, the wonderful old towns. The Majella group presents the highest peaks of the Apennines after the Gran Sasso.

The most challenging step today is located right in the heart of the Majella Park and is considered a must to all cyclists in the area: Passo San Leonardo. It is not uncommon to meet professionals who train on these climbs, from the valley to Passo San Leonardo we climb for 30km. The toughest stretch is about 12%, the average of about 4%. From the pass we descend again following the Apennines to reach the stone town of Pescocostanzo, through the Valley of the Sun.

Hotel in Pescocostanzo.

Day 11.  Pescocostanzo to Bagnoli del Trigno.

Distance 70 km  •  Total Ascent 900 mt

A kind of rest day after two Apennines stages. A well deserved rest is in store for you as we have scheduled a shorter ride of only 70 km to reach the village of Bagnoli del Trigno, with the first part of the route downhill. We will entry in Molise region, one of the most unknown region of Italy and with a very low density of population. The high hills looking at the center west coast are characterized by clay soil and dense vegetation, plenty of colorful flowers.

From the lower ranges of the Majella we reach the valley of the Sangro river, which marks the border with Molise, and then continue on the green hills of Molise, up through the small town of Pescopennataro. Here we stop for a coffe and to admire the incredible view from the old tower. Carrying on we pass the fir trees park and the Rosello forest. Tradition has it  that Agnone is built on the ruins of the city Sannitica Aquilonia destroyed by the Romans during the conquest of Sannio. Agnone is especially famous for the manufac- ture of bells, and one of the oldest in the world. We stop in Agnone for lunch, the town is on the top of the hill and dominates all the valley, there are many terraces offering stunning views.

From Agnone we carry on towards east, mainly on downhill, to reach the Trigno valley and the small town of Bagnoli.

Hotel in Bagnoli del Trigno.

Day 12.  Bagnoli del Trigno to Termoli.

Distance 90 km  •  Total Ascent 1300 mt

The road are more like cross country style but the view really worth the effort. From the countryside of Alto Molise today we head towards the coast trough minor roads, along the ridges, surrounded by wild countryside, with the profile of the Apennines in the distance. A ride through bucolic landscapes and small villages, as we cycle up and down the hills of alluvial clay, through sunflower fields and olive groves as far as the eye can see. First stop in Trivento villages. Once on the coast, we head to Termoli, an old walled city overlooking the Adriatic Sea, next to a long beach. The old town is a well preserved fortress, with white stone buildings, a beautiful cathedral and narrow roads to explore.

Hotel in Termoli.

Day 13.  Termoli to Peschici.

Distance 135 km  •  Total Ascent 1400 mt

Moving south on our journey through Italy, we ride first inland, on the big plain that provide most of the vegetables to the italian markets, finally reaching the coast, arriving in the park of Gargano. This limestone promontory is plenty of caves and caverns, but also cloaked by coastal forests of pine and oak trees, crops of almond, orange and olive trees. In the second part of the ride, the low and sandy coast gradually becomes steep with high limestone cliffs that open into coves of fine sand. The interior is largely covered by the Umbra Forest, which wraps the cape with beech and pine trees, forming the heart of the Gargano National Park. In this lush vegetation, perhaps the richest in southern Italy, the towns, as Peschicici, have preserved their ancient structure, with winding streets and whitewashed houses.

Hotel in Peschici.

Day 14.  Peschici to Manfredonia.

Distance 110 km  •  Total Ascent 1800 mt

Today’s route was used many times for the Giro d’Italia, and it will see the pros racing here also in the 2017. There a simply reason for that: it is a spectacular journey along the coast, with extraordinary views of the sea. Vieste old city center, on the top of the limestone cliff, really worth a visit. Next stop will be in Mattinata, a white town all surrounded by olive trees, just before the last climb of the tour.

The last long climb of the tour, along a gentle and quiet road, bring us to Monte Sant’Angelo castle. From here we can enjoy a great view of the Adriatic coast towards south. A long and curvy downhill bring us to Manfredonia. Manfredonia, our destination for the day, is a fortified town that still retains the castle and has a beach of fine white sand. It’s the ideal place to enjoy the beauty of this peninsula.

Hotel in Manfredonia.

Day 15.  Manfredonia to Altamura.

Distance 130 km  •  Total Ascent 1100 mt

Our ride today marks the real entrance into Puglia, the heel of Italy. It’s a distinctive region, a peninsula between two seas, the Adriatic and Ionian Sea. It was the gateway to the east as well as being enriched with different and varied ancient cultures: Roman, Turkish, Greek and Spanish citizens have left a unique mix in its landscape, architecture, language and culture, as well as in the kitchen! Our destination today is the town of Altamura, which we will reach by crossing the limestone plateau of the ‘Murgia‘. Along the way, we cannot miss a visit to the Castle of Frederick II of Swabia in Andria, with its unique hexagonal shape. On the plateau we pedal through the endless olive groves, interrupted only by the vineyards and field crops that cover this plain.

Altamura is famous worldwide for its characteristic bread which we will definitely try (perfect carb-loading!). All the cuisine is very delicious. It is a city that deserves interest because of its long and rich history. Frederick II gave new impetus to the city by building a cathedral and repopulating the town with Arab, Greek and Jewish immigrants. In that period, the town took a new shape with the construction of ‘cloisters‘, small squares surrounded by alleys. It is this characteristic layout that makes the town such a fascinating place to explore.

Hotel in Altamura.

Day 16.  Altamura to Alberobello.

Distance 100 km  •  Total Ascent 800 mt

Today’s route will take us to discover two beautiful cities unique in the world: Matera, the Stone city, and Alberobello, the town of Trulli. Matera will give us the chance to add another name to our already long list of world heritage sites recognized by UNESCO, all visited in this Journey along the “Bel Paese”. The Sassi of Matera, declared UNESCO World Heritage Site in 1993 represent, for the visitors an unforgettable experience for the landscapes, for the history and for the anthropological value. Cradle of the rural civilization, is the maximum representation of how the man, settling in a barren and hostile territory, has adapted nature to their needs. Walking along the narrow streets and the balconies inside the Sassi, give to the visitor, the sensation to be a witness of an intence cultural experience: from the nature to the local culture, from handicraft art to the Rock Churches.

“The Sassi of Matera and its park are an outstanding example of a settlement dug into the rock, perfectly adapted to its geomorphological environment and its ecosystem. They are an excellent example of a traditional use and settlement the human land showing the evolution of a culture that has maintained a harmonious relationship with its natural environment “ (UNESCO site).

Hotel in Alberobello.

Day 17.  Alberobello to Lecce.

Distance 130 km  •  Total Ascent 500 mt

From Alberobello, among ancient olive groves and vineyards we reach the town of Ostuni. Visible from far, Ostuni, in fact, dominates the landscape from the top of the hills. It is the White city of art; located in the plateau of “Murge”, it is certainly one of the most beautiful places in Puglia. The whiteness of the houses in the historic center is due to the lime, which for centuries has been used for painting the walls. The town itself can be considered an outdoor mu- seum: the narrow streets of the historic center, the Cathedral, the beautiful portals, the sanctuaries, the majestic perimeter walls and towers. The symbol of the town is the Obelisk of Sant’Oronzo, located in Piazza della Libertà.

Even in Ostuni, as in most of Apulia, the history has been marked by invasions and dominations that have left different influence and cultures. But our trip must go on, so we are heading to Lecce, through quiet internal roads, mainly flat, and then along the last section along the coast overlooking the Adriatic sea. Lecce, known as south Flor- ence; is almost entirely decorated in a very typical baroque style called “Barocco Leccese”. With the friable local stone, called “pietra leccese”, easily worked with warm colors, have been realized many architectural decorations of a rare beauty and elegance.

Hotel in Lecce.

Day 18.  Lecce to Santa Maria di Leuca.

Distance 110 km  •  Total Ascent 900 mt

For the last stage of our Italy’s ride, we chose a route that follows the coast to reach to the southernmost point of Puglia, Capo Santa Maria di Leuca, and along the way besides admiring the wonderful limestone coast, we can visit the charming town of Otranto. Its cathedral is the largest in Puglia and preserves one of the largest mosaics in the world. But perhaps the sight of the emerald sea is more attractive than artistic beauty, and most of us will prefer to enjoy a nice break, simply lulled by the blue sea that fills our eyes, just next to the city walls.

How difficult will be to leave these places. The road continues winding along the coast up and down, with many sections on the edge of the limestone cliff. Here the vegetation is more varied and lush than the rest of Puglia; we cross the Otranto park and Tricase wood, until  we reach the Cape of Santa Maria di Leuca, the southernmost point of the heel of the boot. In front of us the sea, behind us a lot of unforgettable memories.

Hotel in Santa Maria di Leuca

Day 19.  Departure