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Destinations (83)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Destinations (83)
Types of Cycling / Grades (7)
Departure Month
Level of Support
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Guided
Grand Traverse Classic - North to South
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 21/05/2026 Last Spaces | 06/06/2026 | £4,195.00 |
| 24/09/2026 Guaranteed | 10/10/2026 | £4,195.00 |
- 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!
Guided
Grand Traverse Explorer - South to North
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/04/2026 | 16/05/2026 | £5,495.00 |
| 29/08/2026 Guaranteed | 19/09/2026 | £5,495.00 |
- 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 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 from the most south-easterly point of the heel of Italy up to Venice, having ridden nearly 1,100 miles and climbed almost 22,000 metres!
Not sure which trip's right for you? Just ask!
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News, Reviews & Stories
Meet the Guides: Josiah Skeats
Meet Josiah (Jo), our UK cycling guide whose love of big adventures began far from home.
Meet the Guides: Ruth Taylor
Meet Ruth, lifelong outdoor enthusiast and one of our incredible cycling guides in the UK.
Wine, food and cycling pairings
Pull the cork on a bottle of wine and begin an armchair journey to some of our favourite cycling destinations...