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The longest cycling climbs in Italy. From this page you may navigate to the top 10 Longest bicycling climbs in Italy. The IT longest bike climbs we have documented are featured in the slideshow below. Scroll down this page to access the Italian Longest 10 Bicycle Climbs "Table". The cycling climbs covering the most distance in Italy, and some of the hardest and most scenic bicycling climbs this state are, in order of distance, 1. Mount Etna, 2. Reggio Calabria, 3. Colle del Nivolet (Locana), 4. Colle del Gran San Bernardo, 5. Colle dell'Agnello - Italy, 6. Blockhause (Fara Filiorum Petri), 7. Gran Sasso d'Italia, 8. Passo del Rombo , 9. Monte Grappa - Caupo, and 10. Monte Grappa - Romano d'Ezzelino.