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Italy - Grand Traverse - North to South (17 days) - Guided Road Cycling Holiday

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, Assisi and Lecce
  • The camaraderie of your fellow cyclist who’ll be joining you on this incredible tour
  • Immersing yourself in Italian culture – meet the friendly locals, experience delicious culinary specialities and taste the wines of each region
  • Cycling to the most southerly point of Italy, having ridden nearly 1,100 miles and climbed 21,700 metres!

View Holiday Schedule

Day Description Distance Ascent Meals
1 Arrival: Pisa / Cinque Terre Non Riding Day    
2 Cinque Terre to Carrara Riviera 55 Miles / 90 Kms Approx. 1,500 Metres Approx. B L  
3 Carrara Riviera to San Gimignano 75 Miles / 120 Kms Approx. 1,500 Metres Approx. B L  
4 San Gimignano to Pienza 65 Miles / 110 Kms Approx. 2,100 Metres Approx. B  
5 Pienza to Assisi 75 Miles / 120 Kms Approx. 1,600 Metres Approx. B L  
6 Assisi to Monteleone di Spoleto 65 Miles / 110 Kms Approx. 1,500 Metres Approx. B L  
7 Monteleone di Spoleto to Santo Stefano di Sessanio 80 Miles / 130 Kms Approx. 2,800 Metres Approx. B D  
8 Santo Stefano di Sessanio to Pescocostanzo 75 Miles / 120 Kms Approx. 2,300 Metres Approx. B L  
9 Pescocostanzo to Campobasso 70 Miles / 115 Kms Approx. 1,700 Metres Approx. B  
10 Campobasso to Termoli 56 Miles / 90 Kms Approx. 750 Metres Approx. B L  
11 Termoli to Peschici 77 Miles / 125 Kms Approx. 1,000 Metres Approx. B L  
12 Peschichi to Santa Margherita di Savoia 87 Miles / 140 Kms Approx. 2,000 Metres Approx. B  
13 Santa Margherita di Savoia to Altamura 62 Miles / 100 Kms Approx. 1,100 Metres Approx. B  
14 Altamura to Alberobello 62 Miles / 100 Kms Approx. 800 Metres Approx. B L  
15 Alberobello to Lecce 77 Miles / 125 Kms Approx. 575 Metres Approx. B L D  
16 Lecce to St Maria di Leuca 70 Miles / 115 Kms Approx. 1,000 Metres Approx. B  
17 Departure: Santa Maria di Leuca / Bari Non Riding Day   B  

Key: B - Breakfast, L - Lunch, D - Dinner

For more information download our trip notes

Holiday Information

For what seems like years we've been planning our 'perfect' route down the length of Italy. Ideas scribbled metaphorically on napkins, suggestions from friends and input from locals with knowledge of the amazing roads hidden away from the tourist gaze have all been combined to produce this epic route. We've fitted an incredible amount into the itinerary, and you should be able to head home at the end of the tour having seen the very best that Italy has to offer.
What better location to start than magical Cinque Terre - this stunning region famed for its dramatic landscape and villages perched on the side of the coastal cliffs. As we leave our accommodation and start riding, our first day is a true taster of what is to come, stunning scenery, great roads and full-immersion into Italian culture. Staying on the coast for a further night, we then say farewell to the Tirrenean sea to head south west towards the southern end of the Apennines, famous for the Carrara marble. Riding though 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: 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 with few visitors, so has kept its genuine character and natural beauty. Riding through the regions of Abruzzi and Molise, we go from one National Park to another: 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 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 though small towns of picturesque Baroque architecture and indulging in its renowned regional cuisine. Our journey is coming to and 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 end 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 centre of Lucca, the historical centre of Siena, Val d'Orcia, the historical centre of Pienza, the castle of Frederick II of Swabia in Andria (Castel del Monte), the Sassi and 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), this trip could well be the perfect way to experience the best that Italy has to offer. 

For more information download our trip notes

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17 days

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Holiday Summary

17 days
Estimated flight price:


Bike Hire:
Single Room:

Holiday Details

Place to place

16 nights hotels & agriturismo

15 days riding

Breakfasts, 9 picnic lunches and 2 evening meals

Guided and vehicle support

Group airport transfers

Luggage transfers

GPS device inc pre-loaded routes

Customer Photos


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Skedaddle Italia Srl is registed Tour Operator in Italy. Registred No. 406, VAT No. 03592410926. Reg. office: Via Caravaggio 10, Assemini, 09032, Sardinia, Italy

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