As the official shouted “3-2-1! Go,” nearly a thousand international and local runners sprinted off the starting line with “The Final Countdown” blaring over the speaker.In the sultry darkness, I could feel sweat dripping down my shins with each stride. It was 5 a.m. and already nearly 80 degrees on a breathless December morning in Grand Cayman for the 13th annual Intertrust Cayman Island Marathon, Half Marathon and 4-person Relay.

As the train doors opened in Trani, a bustling Italian seaport on the Adriatic Sea known as “the pearl of Puglia,” fresh salty sea air filled my lungs. Michele Cappiello, owner of Bike Basilicata, greeted me with a warm smile. I followed him to a small shop nearby, where I changed into Pearl Izumi cycling togs, picked up a provided Scott road bike and maps and began a three-day cycling trip across Puglia and Basilicata in south Italy, a.k.a the heel of “the boot.”