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Italy - Grand Traverse - South to North (22 days) - Guided Road Cycling Holiday

Holiday Highlights

  • Riding up 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: Lecce, Assisi, Siena, Venice
  • 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 from the most southerly point of the heel of Italy up to Venice, having ridden nearly 1,100 miles and climbed 21,700 metres!

View Holiday Schedule

Day Description Distance Ascent Meals
1 Arrival: Bari Airport Non Riding Day    
2 Santa Maria di Leuca to Lecce 60 Miles / 100 Km Approx. 820 Metres Approx. B  
3 Lecce to Alberobello 75 Miles / 125 Km Approx. 950 Metres Approx. B L  
4 Alberobello to Altamura 65 Miles / 105 Kms Approx. 940 Metres Approx. B  
5 Altamura to Margherita di Savoia 60 Miles / 100 Km Approx. 600 Metres Approx. B L  
6 Margherita di Savoia to Peschici 78 Miles / 130 Km Approx. 1,500 Metres Approx. B L  
7 Peschici to Termoli 77 Miles / 125 Km Approx. 1,000 Metres Approx. B  
8 Termoli to Campobasso 55 Miles / 90 Km Approx. 1,800 Metres Approx. B L  
9 Campobasso to Majella Park 70 Miles / 115 Km Approx. 2,400 Metres Approx. B L  
10 Majella Park to Santo Stefano 65 Miles / 105 Km Approx. 1,800 Metres Approx. B L  
11 Santo Stefano to Cagnano Amiterno 50 Miles / 80 Km Approx. 1,400 Metres Approx. B L  
12 Cagnano Amiterno to Monteleone di Spoleto 40 Miles / 60 Km Approx. 950 Metres Approx. B L  
13 Monteleone di Spoleto to Assisi 65 Miles / 105 Km Approx. 1,000 Metres Approx. B  
14 Rest Day: Assisi Non Riding Day   B  
15 Assisi to Pienza 77 Miles / 125 Km Approx. 1.700 Metres Approx. B  
16 Pienza to Siena 43 Miles / 70 Km Approx. 1,100 Metres Approx. B  
17 Siena to Chianti Region 50 Miles / 80 Kms Approx. 1,300 Metres Approx. B  
18 Chianti region to Castrocaro Terme 68 Miles / 110 Kms Approx. 1,400 Metres Approx. B L  
19 Castrocaro Terme to Comacchio 62 Miles / 100 Kms Approx. 200 Metres Approx. B  
20 Comacchio to Chioggia 68 Miles / 110 Km Approx. 250 Metres Approx. B L  
21 Chiogga to Venice 12 Miles / 20 Kms Approx 10 Metres Approx B  
22 Departure: Venice Airport Non Riding Day   B  

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

For more information download our trip notes

Holiday Information

Out of popular demand and request, we have put together the ultimate 21 day - Italy Traverse from South to North and what better way to end than the magical Venice - this stunning city, criss-crossed with a dense network of canals and home to some of Italy's finest architecture is a great finale to our journey across Italy. Starting in the 'heel of Italy', the most southern point of St Maria di Leuca, we have planned our 'perfect' route up the length of Italy. We've fitted an incredible amount into the itinerary, and you should be able to go home at the end of the tour having seen the best that Italy has to offer!
Throughout the trip we will have the opportunity to visit and ride through 10 World Heritage sites recognised by UNESCO: the Sassi and the Park of the Rock Churches of Matera and the trulli of Alberobello, the castle of Frederick II of Swabia in Andria (Castel del Monte), the historical centre of Pienza, Val d'Orcia, the historic centre of Siena, the Po delta and Venice and its lagoon. 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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Prices From:

€4,360 p.p.

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Holiday Summary

21 days
Estimated flight price:


Bike Hire:
Single Room:

Holiday Details

Place to place

21 nights hotel accommodation

19 days riding

1 rest day

Breakfast and lunch

Guided with vehicle support

Airport transfers

Luggage transfers

GPS device inc pre-loaded routes

Customer Photos


Skedaddle News, Views and Holiday Stories

Double fun on Italy’s Grand Traverse

With her tandem in tow Skedaddler Jill Buzzard headed to Italy earlier this year to take on our 1,000 mile challenge, the epic Italian Grand Traverse. Here’s how she got on… Prelude “A tandem” said our guide. “Well … we…

The post Double fun on Italy’s Grand Traverse appeared first on Skedaddle Blog.

Last Updated: 06/09/2016

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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