I first met Alessandro di Benedetto on a dock in November 1992 in Las Palmas de Gran Canaria, as we were both preparing to sail across the North Atlantic from the Canary Islands to the Bahamas to commemorate the 500th anniversary of Columbus' voyage to America. I was crewing on an Australian-owned Taswell 56 called Antipodes that was enrolled with 145 other yachts in Jimmy Cornell's America 500 rally. Alessandro planned to cross with his father on a 18-foot Hobie Cat called United States of the World.
As I remember, Alessandro was the quiet one; his father, Federico, was the voluble, talkative one. They roamed the docks where all the rally boats were tied up handing out photocopies of a letter they had sent to the Secretary General of the United Nations. In the letter they explained that the purpose of their voyage was to help establish a new democratic international order based on economic justice and environmental responsibility. Not surprisingly, they were often referred to casually as "those crazy Italian guys."
Alessandro and his dad were in fact part of a small crowd of enthusiastic hangers-on who proposed to sail in company with the America 500 fleet without having formally joined the rally. Most rally participants had no problem with this, but Jimmy Cornell wasn't too happy about it. I did not attend the last skipper's meeting held in Las Palmas, but I heard from several who did that Cornell prohibited skippers from sharing the rally's radio frequencies and urged that participating boats not render assistance to others outside the rally. The skipper on my boat was outraged by this and considered it a gross violation of international law.
Predictably enough, one boat that did require assistance sooner rather than later was United States of the World. In the photo up top you see her at the start of the rally. The next and last time I saw her, less than 24 hours later, she had been taken in tow by an America 500 boat just off the coast of Gomera, two islands west of Gran Canaria, and was headed into port. I heard later that the skipper of the boat rendering assistance was indeed chastised by Cornell for having done so. I also later learned that Alessandro and Federico, though they failed in their attempt to sail to the Bahamas with the rally fleet, did ultimately succeed in crossing the Atlantic that winter.
Since then Alessandro has distinguished himself as a singlehander in his own right and has set two world records. In 2002 he sailed from Las Palmas to Guadeloupe and became the first singlehander to cross the Atlantic non-stop on a small open catamaran; in 2006 he duplicated the feat in the Pacific, crossing non-stop on an open cat from Yokohama to San Francisco.
(Alessandro and his 20-foot cat One World in San Francisco)
Last fall Alessandro set out to establish a third world record for smallest vessel to circumnavigate non-stop. He set out from Les Sables d'Olonne in France on October 26, 2009, aboard a modified 21-foot Mini called Findomestic Banca (after his title sponsor) and is now in the Southern Ocean approaching Australia's Cape Leeuwin. His website doesn't provide much detail and the English translation is spotty, but near as I can tell things have gone smoothly so far.
The boat certainly looks rugged. The hull has been thoroughly reinforced, the rig has been cut down and beefed up, and a rather massive-looking fixed carbon-fiber bowsprit had been grafted on to the bow. The most intriguing feature is the (relatively) large cabinhouse that has been built on to the stern. In a capsize Alessandro hopes the cabin's shape and the added buoyancy aft will help the boat quickly right itself. He can also steer the boat from inside the cabin in heavy weather.
For those tempted to think Alessandro is in fact crazy, I suggest you watch this video interview posted at YachtPals. He comes across as very calm and deliberate (much like the Alessandro I met in 1992) and his brief, almost laconic response to a specific question about his being crazy suggests he is anything but.
For those thinking Alessandro might also gain the record for smallest boat to complete any sort of circumnavigation, please be advised this is currently held by an Australian, Serge Testa, who completed a circumnavigation (making stops and via the Panama Canal) in an 11-foot boat in 1987.
If you ask me, he's the one who might be a little crazy.