From theater to regattas: who is Massimo Piparo, shipowner with a great passion


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IY 11.98 Guardamago II

Director, author and producer of the biggest theatrical and TV hits of recent years, Massimo Piparo is the man who brought the Italian musical to the center of the international stage (“Jesus Christ Superstar,” “Mamma Mia!”…do these names ring a bell?). But Piparo, and this interests us, is also a true sailor: 56 years old, originally from Messina, he is one of the rising shipowners in the Italian offshore scene. With his Italia Yachts 11.98 Guardamago II, he has just finished in second place in the Mediterranean ORC Championship races, confirming himself as one of the top boats in Italy. We interviewed him to get to know him better and find out about his journey as a sailor and owner.

Massimo Piparo
Massimo Piparo

Our interview with Massimo Piparo

Where did the passion for sailing come from?

I started because I was born in Sicily by the sea, in the Strait, half the year I had the Strait in front of me and the other half I had the Aeolian Islands because I frequented the area of Milazzo and Capo d’orlando. The sea in short was somehow in my destiny. I started sailing with my first rudimentary dinghies as a young boy, then I experienced the period of the arrival of sailboards that kidnapped me and I started going.

Massimo Piparo at the helm of Guardamago 2
Massimo Piparo at the helm of Guardamago 2

In the meantime, as I became an adult, I started to travel around Italy for work, and I kind of moved away from sailing; the offshore came in a second phase, when I started to have time again to cultivate my passion. I am now at a career stage that allows me to organize my time well, and I can “steal” the time I need for my hobby, partly because my first major sponsor is one of my companies that handles the distribution of shows and also invests in sailing.

Why did you choose Italia Yachts and why specifically the 11.98?

Massimo Piparo
Guardamago 2

I used to do a lot of cruising and had more cruise boats than racing boats, then slowly I got a First 40, then a Sun Odyssey 42 Performance, then after a period of racing with a First 45 that I didn’t own I got in touch with the Italia Yachts shipyard and my sailing horizon changed by better understanding what kind of boats can be winners. I also started racing with professionals who helped me improve quickly and better understand certain dynamics for crew sailing.

What was the process of bringing your boat up to the results of the last few weeks?

Duel between Guardamago 2 and Scugnizza, two IY 11.98.

Professionals certainly help to improve, but I am a somewhat “atypical” shipowner perhaps because I insist on helming, and I invested in this project starting with the helmsman-owner, who cannot be just someone who turns the wheel but must have awareness.

I had Giovanni Sanfelice of North Sails as my first “coach,” who also directed me to this boat and today is in charge of Guardamago’s designs. Also a key pawn in the last season was Claudio Arborea, who put in a lot of effort to improve boat and crew. The key is to be willing to learn and try to do it with the right people.

Where did the name Guardamago come from?

Romans may know this story. In Rome 20 years ago, a Pakistani clown, magician and conjurer, who called himself the Magician Guarda and became one of the idols of Roman evenings, roamed the historic center. He would do a show that always ended with the phrase Look 1, Look 2, Look Magician. My first boat, the Sun Odyssey, I named it Guardamago and so on with all of them. Also because I call mine “the show boat,” we have fun even when we lose, and it kind of reflects the name Guardamago.

The best regatta you have participated in so far and why

I am very attached to the 2019 Italian ORC Championship in Crotone, because the boat had just left the yard, still not quite finished inside, and it was my first step into top-level racing with professional sailors. Although there were not as many boats, it was the first step toward the Guardamago that it is today, beginning to figure out how to aim high. Then I have a wonderful memory of the Long Bolina 2021, won in class C and doing a third overall, in very tough conditions that decimated the fleet, we managed to finish it, and it was the first regatta with Arborea as tactician.

Only racing or also cruising? Favorite destination?

Of course also cruise. My favorite destination is the Aeolian Islands, which I have now done in all sauces and in all possibilities, but not with this boat on a cruise, this one is now designed and equipped for racing, now I go for charter when I want to go on vacation.

The regatta you dream of doing? With which boat?

With this boat I already feel at the top, and I am so attached to her. With Guardamago I would like to do first of all the Palermo-Montecarlo, also because as a Sicilian I would have a double motivation in participating in it, and then the Middle Sea Race, which I have done with a First 45 and I would love to try it with Guardamago. Who knows, in the future I think we will try even though it is certainly a complex regatta.

Mauro Giuffrè



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