Skipper Paolo

Paolo’s Sailing Story



I was born in Siena, Italy. While the world’s attention was focused on the exploits of the athletes in the 1960 Rome Olympics, my parents soon made the short journey to take me to the shores of the Tyrrhenian Sea.

Since Italy is a narrow peninsula, even if you were born inland, the sea is never far away and therefore very common that it becomes an integral part of your life.


Later, when my parents bought a beach house overlooking the sea at Castiglione della Pescaia, I naturally started taking sailing lessons with my friends; first sailing with friends’ dinghies and then with my own. The next step was to convince my father to buy a small cabin cruiser to be able to navigate the islands of the Tuscan Archipelago and beyond. Although my father was measured in his spending, I managed to leverage his love of nature, to convince him to buy a Finot design sailing boat called a Comet 800 (24 feet).



With the Comet 800, and a family crew, we visited the whole Tyrrhenian Sea and the Ligurian Sea, from Portofino to Capri, up to Corsica and Sardinia.


We also tried to do a few series of club regattas with friends, although the results weren’t striking. Of those years I always remember the enthusiasm with which each navigation was faced, and the wealth of experience gained in a boat in which the only instrumentation was a log/speedometer and an echo sounder with a range of 20 meters – so only useful in shallow waters.


A few years later, after my son was born and I had graduated in Law, I sold the Comet 800, and after a short break, bought a Hanse 341. This enabled me to venture even further with the range of my cruising, although still being limited in time I could spend sailing by work commitments. I also had to take my son to his sailing lessons and regattas on the coast every weekend – whether this was in the freezing cold, pouring rain, or glorious Tuscan sunshine – as he was growing up to be the natural, skilled sailor he is today.

I met Jennifer through Find-a-Crew, when we were both looking for the other part of the circle to make a whole. I had a boat and needed crew and she needed a boat and company to sail with.


Since then, we have travelled many miles, always together… and it wasn’t too long before we discovered our mutual, long held desire to sail and travel full time. We began to hatch a plan to leave our respective careers early, to live on a boat and travel the world.



Read More: Becoming a Liveaboard Skipper



Skipper Paolo’s Qualifications

  • RYA Yachtmaster – Commercially Endorsed.
  • Italian Sail & Motor Unlimited Licence.
  • STCW Safety Training for Mariners Endorsements – 
    • Personal Sea Survival Techniques
    • First Aid and CPR
    • Basic Fire Fighting
    • Personal Safety and Social Responsibilities
    • Proficiency in Security Awareness