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Grand Traverse Classic - North to South

Guided Road Cycling Holiday




17 days

Prices from

£4,195 P.P.
What better location to start your cycling journey through Italy than the magical Cinque Terre - this stunning region famed for its dramatic landscape and villages perched on the side of the coastal cliffs. A true taster of what is to come; stunning scenery and full immersion into Italian culture. It's not long though before it's time to say farewell to the Tyrrhenian Sea to head south west towards the southern end of the Tuscan Apennines, famous for the Carrara marble. Riding through nature reserves and small Italian villages and towns this is a great introduction to northern Italy.
Taking quiet roads and small mountain passes, we cross into Tuscany and from beautiful Lucca we carry on south through the green hills of Chianti, onto the rolling clay and chalk landscapes of the Crete Senesi and the UNESCO site of Val d'Orcia. Here we start picking up momentum as we head into the Apennines again, exploring Umbria; a land of small and beautiful medieval villages perched on limestone hills. Following the Apennine range south, we ride through a part of Italy that is truly authentic, and with few visitors, so has kept its genuine character and natural beauty. Riding through the regions of Abruzzio and Molise, we go from one national park to another; the Park of Gran Sasso, Majella Park and the Park of Matese.
From the Apennines we head next towards the Adriatic coast, then south towards the Gargano region of Puglia (the heel of Italy) through the soft clay hills and sunflower fields of Molise. More surprises are in store for us as we enter Puglia, riding through small towns of picturesque Baroque architecture and indulging in its renowned regional cuisine. Our journey is coming to an end as we follow the coast on the heel of Italy, enchanted by the crystal clear waters of the Strait of Otranto, finally reaching the very tip of Italy.
Throughout the trip we will have the opportunity to visit and ride through several World Heritage sites recognised by UNESCO: Cinque Terre, the historic centres of Lucca, Siena and Pienza, Val d'Orcia, the castle of Frederick II of Swabia in Andria (Castel del Monte), the Sassi, the Park of the Rock Churches of Matera and the trulli of Alberobello. With a combination of superb riding, incredible scenery, fantastic Italian food and wine and plenty of opportunity to experience La Dolce Vita; the good life, cycling in Italy on this trip could well be the perfect way to experience the best that this incredible country has to offer. 

Holiday Highlights

  • Riding down the backbone of Italy on a stunning route which takes in some of the best road cycling that Italy has to offer
  • Cycling through 10 UNESCO World Heritage sites and 5 National Parks
  • Visiting some of the most important historical and artistic cities in Italy: Lucca, San Gimignano, Pienza, Assisi and Lecce
  • The camaraderie of your fellow cyclists who’ll be joining you on this incredible tour
  • Immersing yourself in Italian culture – meeting the friendly locals, experiencing delicious culinary specialties and tasting the wines of each region
  • Cycling to the most southerly point of Italy, having ridden nearly 1,100 miles and climbed over 21,000 metres!

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If someone was going to do just one of Skedaddle’s trips, it should be this one!

Nigel, Hampshire


Day 1
Arrival: Pisa / Cinque Terre
Non Riding Day

Leaving Pisa airport (PSA) we take the 90 minute transfer to Cinque Terre where we enjoy the first of many hotel stays for the trip. Today we will build our bikes, get to know each other and get ready for our tremendous journey ahead!

Day 2
Cinque Terre to Carrara Riviera
56 Miles / 90 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,500 Metres Approx.

What better official start to our Italian Grand Traverse than riding from the northern part of the Cinque Terre, known as the ‘Gateway‘, through the whole of this UNESCO Heritage site to then reach the Massa Carrara Riviera in Tuscany. People normally associate Cinque Terre with fabulous walking along the cliffs, reaching beautiful villages and drinking Limoncello at sunset, but very few people mention the cycling. Staying high up on the ridge, with options to drop down into the many amazing villages, the panoramic views are amazing and the riding spectacular; vineyards, olive groves, farm terraces and trees bearing yellow, sweet lemons, with a backdrop of deep blue Mediterranean Sea, make up for every centimetre of climbing along the coastal route south.

We drop into La Spezia, a busy town and important Mediterranean port, a sharp contrast to the start of the day, but an ideal location to stop for a re-group and a re-fuel before moving on down the coast. We are leaving the hilly regions and for the latter part of the day we will be riding along the Riviera of Carrara, on the edge of the Apennines. The white peaks which we will keep on our left as we ride down the coast are a reminder of the famous marble quarries that Michelangelo favoured for all his great work, including the statue of David in Florence.

We stay on the Riviera for the night, and weather permitting we can take a dip in the Med to end wonderfully our first day in the saddle.

Day 3
Carrara Riviera to San Gimignano
75 Miles / 120 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,700 Metres Approx.

After breakfast, it’s time to say goodbye to the Thyrrenian coast as we ride inland, towards the lower hills of the Apennines, on our way to Lucca. A couple of switchbacks lead us through a mixture of woodland and pastures where we follow some minor roads. These roads lead us into Tuscany, where we reach the high point of this morning near Piazzano, then descend into the Serchio Valley. Riding along the river on a car-free cycle path, we enter Lucca through one of the many gates of the fortified city. We can’t come to Lucca without riding along the perimeter of the city walls, joining the many locals and stopping in the piazza for a coffee break.

Our route continues south of Lucca and we are now heading towards the heart of Tuscany, where we start to recognise the pictoresque landscape that makes this region so attractive to cycle in. The route becomes a roller coaster ride past farm holdings, olive groves and small vineyards, interspersed by dramatically perched hamlets on hill tops. One of these is our home for the night, San Gimignano, the town of towers, silhouetted on the horizon as we approach from the north. In San Gimignano, we celebrate the day’s achievements with an ‘aperitif’ in the Piazza and our first taster of Tuscan regional delights.

Day 4
San Gimignano to Pienza
65 Miles / 110 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,800 Metres Approx.

Another full day of riding through the best that Tuscany has to offer. Leaving San Gimignano, we start with a fast sweeping descent to the lower plains of Poggibonsi, to then ride up gently into the Chianti region, over alluvial hills ideal for the growing of San Giovese vines that transform into the world famous Chianti DOC red wine. Vineyards alternate with dense woods as we make our way to Siena. Our coffee break is in Piazza del Campo in Siena, famous for the Palio and with the dramatic Duomo in the background, an idyllic stop before we hop back on our bikes.

Moving towards the Val d‘Orcia, the landscape changes yet again as we roller-coaster along the clay hills lined with cypress trees so typical of the Tuscan landscape. Along the way, we ride through Asciano and San Giovanni d‘Asso, well-preserved medieval towns, that add to the charm of this area and make for another well-deserved fuel stop.

The last few miles of our journey are spent riding through the walnut-clad wooded hills with the small villages of Montisi and Castelmuzio eventually leading us in to Pienza.

Day 5
Pienza to Assisi
75 Miles / 120 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,400 Metres Approx.

Today we leave Tuscany to discover Umbria, the green heart of Italy. An ideal destination for those who enjoy responsible tourism, Umbria is an enviable mix of history, nature and art. The entry into Umbria is the most spectacular, thanks to the beautiful scenery of Lake Trasimeno.

From Castiglione del Lago, we head along the south shore of the lake before turning off and heading south to explore the green hills of Umbria leading towards Assisi, the city of Saint Francis. Assisi is above all a splendid city of art. It would be unforgivable to miss a short visit to its historic centre, a UNESCO World Heritage Site. Just outside the walls, dominating the city, there is the magnificent Castle Maggiore, rebuilt in 1367 on an earlier structure (1174) of an ancient feudal castle.

Day 6
Assisi to Monteleone di Spoleto
65 Miles / 110 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,600 Metres Approx.

Tuscany and Umbria are obviously a ‘must’ on our trip, a Grand Traverse of Italy cannot ignore them. But we were faced with a dilemma; to continue south along the coast or stay on the Apennines? We chose the latter option. We wanted to show a side of Italy little-known, but no less beautiful. From this point on our route could be called ‘the tour of the National Parks‘. Let’s start with the Regional Park of Mount Subasio, just outside of Assisi. Then we have, in order; Parco dei Monti Sibillini, the Monti della Laga National Park of Gran Sasso, Parco della Majella and the Park of Gargano.

Today we leave from Assisi and cycle to the charming town of Spoleto, keeping for the most part on a quiet cycle path running parallel to the Clitunno River. From Spoleto we then start climbing up the lower slopes of the Apennines, enjoying the first views of the soaring peaks of the central Italian Apennines. Today’s climb, although not very hard, will be a worthy prelude to our next couple of days in the Apennines. At the end of the day’s ride we arrive at the small hamlet of Monteleone di Spoleto.

Day 7
Monteleone di Spoleto to Santo Stefano di Sessanio
80 Miles / 130 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 2,550 Metres Approx.

From Monteleone di Spoleto today we set off for what is the hardest – and arguably also the most rewarding! – ride of our journey down Italy. We aim for the Gran Sasso National Park, home to the highest peaks of the Central Italian Apennines. During our day we will be climbing to over 1,600m, offering the best view of the imposing limestone peaks of the Gran Sasso. The high plains dominated by the peaks are also know as ‘Little Tibet’ due to their spectacular scenery. Our day’s destination is the tiny mountain village of Santo Stefano di Sessanio, situated on a green hill overlooking a small lake, which has preserved its medieval architecture almost completely.

Day 8
Santo Stefano di Sessanio to Pescocostanzo
75 Miles / 120 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 2,300 Metres Approx.

The Majella Mountain, known locally as ‘the Mother Mountain‘, is part of the Abruzzi Apennines, and is characterised by its high, imposing wild limestone blocks, which are deeply furrowed by yawning valleys, and culminates at Mount Amaro at 2,793m. With its extraordinarily wild nature and its rich historical, archaeological and architectural features, it is a fundamental part of the world heritage of national parks.

Its incredible geographical position, its harshness, dense woodlands, abundant rivers and unstable climate, makes the Majella region, together with the near Gran Sasso and Laga’s Mountains Park as well as Sirente Velino Regional Park, a rare ‘hot spot’ for national bio-diversity conservation which is precious for the many endangered plants and animal species, including wolves and bears.

But it is also a park of ancient hermitages, abbeys, stone huts and some wonderful historic terraced centres perched on the side of steep mountains. The most challenging section today is located right in the heart of the Park of Majella and is considered a ‘must’ by all cyclists in the area. From the valley to Passo San Leonardo it’s a stretch of 30km of gradual climbing, the hardest gradient being 12%, but with an average of about 4%. The scenery is stunning as you gradually ride between the majestic Monte Amaro and Monte Morrone. From the pass we descend again following the Apennines to reach the small village of Pizzoferrato, through the Valley of the Sun.

Day 9
Pescocostanzo to Campobasso
70 Miles / 115 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,700 Metres Approx.

From Pescocostanzo today we cycle onward through the Majella Mountains of the little known and thus largely unspoiled Molise region. In order to get to our day’s destination we wind our way along the deep Molise valleys and into the green hills through the small villages of Castel di Sangro, Pietrabbondante and Bagnoli del Trigno. This is the country of fir trees, and the Abetina Rosello wilderness.

At the end of the day we will arrive at Campobasso, the capital city of the Molise region, which has a long history going back to Roman and medieval times. Most of the city’s main monuments date from more recent times, including the 14th century Castello Monforte.

Day 10
Campobasso to Termoli
56 Miles / 90 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,000 Metres Approx.

From the countryside of Alto Molise today we head again towards the coast. Today is a relaxing ride through rolling landscapes as we cycle up and down the hills of alluvial clay, through sunflower fields and olive groves as far as the eye can see. Once on the coast, we head to Termoli, an old walled-city overlooking the Adriatic.

Day 11
Termoli to Peschici
77 Miles / 125 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,000 Metres Approx.

Moving south on our journey through Italy, from Termoli we first make our way through the low foothills on the border of Molise and Puglia, before descending onto the coast again. Here we arrive in the Park of the Gargano, a limestone promontory full of caves and caverns, but also cloaked by coastal forests of pine and oak trees, crops of almond, orange and olive trees.

The low and sandy coast here gradually becomes steep with high limestone cliffs that open into coves of fine sand, popular with beach-goers in the summer months. 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 have preserved their ancient structure, with winding streets and whitewashed houses.

Day 12
Peschichi to Manfredonia
62 Miles / 100 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 2,000 Metres Approx.

Today’s ride is a spectacular journey along the coast, with extraordinary views of the sea. From Peschici we head further into the Gargano peninsula towards Vieste. The views are spectacular and will only become better when we climb up to the little town of Monte Sant‘Angelo.

The road winding up through the steep and jagged limestone cliffs of this part of the Gargano makes for one amazing ride, topped off by the fast sweeping descent into Manfredonia. This fortified town still retains the castle and has a beach of fine white sand.

Day 13
Manfredonia to Altamura
84 Miles / 135 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,150 Metres Approx.

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!). It is a city that deserves interest because of its long and rich history. In Altamura, fossil evidence of human presence was found dating back to 400,000BC. In 500BC the megalithic walls that gave the town its name ‘High Walls’ were erected. In 1232, Frederick II gave new impetus to the city by building a cathedral and re-populating 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.

Day 14
Altamura to Alberobello
62 Miles / 100 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 800 Metres Approx.

As well as enjoying some stunning riding through the heart of southern Italy, we will get the chance to explore two amazing cities, unique in their kind; Matera, the city of stone, and Alberobello; the famous city of the ‘trulli’ houses.

We will initially call into Matera, home to the world famous, and UNESCO listed, ‘sassi’ houses – ancient cave houses and churches hewn from the local sandstone. A stroll through the ancient alleyways is a very worthwhile experience!

Our overnight destination and second highlight for the day is Alberobello – world-renowned for its conical-roofed stone trulli houses. Another UNESCO world heritage site, Alberobello offers narrow stone paved pedestrianised streets and rows of tiny trulli houses – some of which have been converted into small shops and restaurants, but many of which are still homes to local inhabitants.

Day 15
Alberobello to Lecce
87 Miles / 140 Kms Approx.
  • Meals: Breakfast
  • Ascent: 500 Metres Approx.

On leaving Alberobello, we ride among olive trees and vineyards as far as the town of Ostuni. Visible from a great distance, Ostuni dominates the landscape from the top of the hill. With its ‘white glow‘, Ostuni is considered to be one of the most beautiful places in Puglia. The whiteness of the houses of the old town is due to the lime, which for centuries has been used for painting the walls. Resting on three hills overlooking the Adriatic Sea, it is surrounded by age old olive groves. The city’s main symbol is the obelisk of Sant‘Oronzo, located in Piazza della Libertà.

After leaving Ostuni, we ride on peaceful rural roads, mostly flat, and continue the last stretch along the Adriatic coastline towards our overnight destination, near the city of Lecce. Due to its rich baroque architectural style, Lecce is known as the ‘Florence of the South‘. With the soft local stone easily worked with warm colours, many fine architectural decorations have been made to adorn this magnificent city.

Day 16
Lecce to St Maria di Leuca
62 Miles / 100 Kms Approx.
  • Meals: Breakfast
  • Ascent: 800 Metres Approx.

We are coming to the end of our Italian Traverse and for this last section we have chosen a route along the coast to reach the furthest point of the ‘heel of Italy‘, Cape Santa Maria di Leuca.

Along the way, we will spin our legs, admiring the stunning chalk coastline and stopping for a visit of the enchanting town of Otranto. The cathedral there is the biggest in Puglia and has one of the the best mosaics in the world.

For the final section of the ride, we will take a winding coastal road, high up on the cliffs above the emerald green sea and eventually will arrive at the heel of Italy, the stunning lighthouse at Leuca.

This is the perfect spot to relax, gaze out onto the confluence of the Adriatic and Ionian seas and contemplate the incredible diversity of scenery, architecture, food and peoples that we have experienced during the 2 weeks of our Italian Grand Traverse.

Day 17
Departure: Santa Maria di Leuca / Bari
Non Riding Day
  • Meals: Breakfast

Today we leave our hotel early in the morning to take the 3 hour transfer to Bari airport (BRI). Plenty of time on the journey to regale stories of our adventures together and plan your next Skedaddle adventure!

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The Cycling


Italy’s perfect mix of good weather, fantastic scenery and cycle ‘savvy’ locals means that riding here is a real pleasure. As you travel through Italy, road conditions can be very different depending on the geology of the region and relative ‘wealth‘. The regions further down the boot, in the south for example, are far less rich than the north. In these regions your cycling experience will focus more on riding through and visiting the unique towns and their architecture, some of which are UNESCO Heritage sites.

In order to avoid the busy roads, we will take secondary roads through the countryside with varying quality of tarmac. This trip is one of our tougher road cycling tours and covers quite large daily distances – normally averaging 70 miles/110km per day and there are some big climbing days – a maximum daily total of 3,000m/10,000ft and a daily average of 1,500m/5,000ft. Considering the variety of road surfaces, a bike with 28-inch tyres are recommended.


Road Cycling Grade

Grade 4 : Challenging

45-80 miles / 80-130 kms per day

For cyclists with stamina & a good level of fitness

Long & challenging days with multiple tough or high altitude ascents, with steep sections over extended distances

Long & often technically demanding descents

Road riding for experienced riders

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

You‘re an enthusiast. It’s probably your main hobby and possibly the only sport you take seriously. You‘re in pretty good shape and you ride as often as you possibly can. You might participate in the occasional cyclo-sportive and when you do, you probably opt for the longest distances. You love bikes and fantasise about the latest model or the joy of a new set of wheels. You love challenges and you‘re looking for a tour with plenty of climbing, preferably with an opportunity to tick off some famous Tour de France cols or the like. You‘re a competent descender, and you‘re not afraid of speed, but you ride safely and within your limits at all times. You understand road etiquette and you‘re comfortable riding in a bunch. You‘re happy to do your stint at the front of the pack if the need arises. You know you can ride a century and probably have done a few. It sounds like you are a Grade 4.

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

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We have mourned the end of this wonderful trip! Excellent routes, fantastic cycling, perfect organisation, lovely companions, great food.

Andrew, Oxford

Dates & Prices

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Book now with a £300 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

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Whats Included Tick

A) Accommodation (shared twin / double en-suite rooms)

B) Meals as per the itinerary (B=Breakfast, L=Lunch, D=Dinner)

C) Full support service including a Skedaddle support driver and Skedaddle riding guide

D) Unless stated, at least one leader qualified in First Aid

E) Support vehicle and luggage transfers

F) GPX files provided (GPS units available on request)

G) Airport transfer on scheduled arrival day from Pisa airport (PSA)

H) Airport transfer on scheduled departure day to Bari airport (BRI)

I) Financial Protection through ABTOT

What's not Included Cross

A) Bike rental (available if required)

B) Flights and charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Single room (available if required)

E) Travel insurance

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to museums and other attractions en-route

I) Airport transfers on days other than the scheduled arrival / departure days

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Private Departures

Private Departures

Are you keen to only travel with your family or friends? Struggling to find the right date? Well, we can organise a private departure for this tour and tailor aspects to suit your group's specific needs. Contact our friendly team and we'll help you turn your dream into reality.

The Essentials

Travel Options

Your tour starts in Cinque Terre and finishes in Santa Maria di Leuca. Group airport transfers are included in the cost of your holiday.

To join the airport transfer on arrival you’ll need to arrive into Pisa airport (PSA). At the end of the trip, we will transfer the group to Bari airport (BRI) – possibly via Brindisi if timings allow.

We will provide you with details of suitable flight/arrival/departure schedules as flight timetables become available.

Please check with us before making any travel arrangements to ensure we have reached the minimum number required to guarantee your holiday and to make sure your arrangements fit with our scheduled transfers.

Please note If you make travel arrangements that fall outside of the scheduled transfer windows, there may be an additional charge for individual transfers.


Accommodation (shared twin or double rooms) will usually be en-suite in 3 star hotels or agriturismo. Family run, personable, charming, comfortable and homely are boxes we tick when looking for places to stay. A million miles away from chain style hotels all with unique touches.

Swimming pools and ‘wellness’ centres are available at some of the accommodation, but cannot be guaranteed.

Bike Hire

Rental bikes will typically be a Giant Defy Advanced 2 or Giant Liv Avail Advanced 2 (for those preferring a women’s specific geometry) – or equivalent, with a carbon frame and hydraulic disc brakes.

These are great bikes with good quality components generally equipped with at least one bottle cage, a saddle bag and a small pump.

We can also include a helmet which should be requested at time of booking.

Please note that your bike will come with flat pedals as standard, so please do bring your own if you use clip-in pedals.

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