My wife has family in Calabria. This route, just a few miles from where we stay, has two good climbs: from sea level to 3700 ft in 9 miles and from 2000ft above sea level to 3700 ft in 2.5 miles. the second climb includes a 22% average grade for a KM, climbing 723 ft in that distance. The route provides 5750 ft of climbing in the first 20 miles.

http://www.mapmyride.com/routes/view..._done=1#climbs

The winter-free weather is a plus, too.