He is living on the beautiful island of Elba off Tuscany, is learning Italian and has finally been given a chance to helm.
Life couldn't get much better for Hamish Pepper, who just two years ago suffered the humiliation of being booted off the black boat during Team New Zealand's devastating cup defeat.
Pepper is now with Italian syndicate Mascalzone Latino/Capitalia - the colourful Latin Rascals who made their cup debut in 2002.
He is part of the syndicate's afterguard, which also includes highly regarded Italian sailors Vasco Vascotto and Flavio Favini. His primary role is strategist but he is also the syndicate's backup helmsman and contributes to the design process, giving him a wider role than he ever had at Team New Zealand.
That's something Pepper, nicknamed Pepperoni by his Italian team-mates, is relishing.
The 33-year-old had been asked to trial for Luna Rossa (formerly Prada) but decided the opportunities were greater at Mascalzone Latino.
"I feel I am in the position where I want to be and the opportunities are there for me so I am excited about this campaign.
"I am learning a new language and the Italians are passionate about sailing and life in general. There is a lot of humour in the team. It is a very different atmosphere to Team New Zealand."
Unwanted by the new Emirates Team New Zealand, Pepper, who was dropped as tactician midway through the failed defence, said he considered walking away from the pursuit of the Auld Mug.
"There were times during that last campaign when I definitely wasn't happy and I even thought about quitting the team six or seven months out.
"But I still have a lot of friends there and a lot of good memories."
Mascalzone is predominantly Italian, but managed by New Zealander Tom Weaver. Fellow Kiwi Cameron Dunn is also in the afterguard and other New Zealanders are in the boat-building team.
The team leave their Elba base next month for Valencia, with their newly bought boats USA66 and USA77 (formerly Stars and Stripes), one of which is being modified to comply with the new design specifications.
In the last cup, the syndicate head, Italian businessman Vincenzo Onorato, said his team's main objective was to learn. This time, Pepper said, the syndicate are better funded and are aiming for a top-four spot.
With Team Luna Rossa, Team NZ and Oracle touted as the big three, Mascalzone are probably among the best placed in the next group, which includes France's K-Challenge, Team China, Italy's +39, Sweden's Victory Challenge, United Internet Germany and Spain's Desafio Espanol.
"I think it is going to be a lot closer this time. The boats shouldn't be very different because the design rule is very tight," said Pepper, who is also planning an Olympic campaign in the Star class.
"It could be a close match-racing game. That is where the bigger teams with the really experienced match-racers might come through. We have a lot of people who have won world championships so we just need to get out there and improve so we can be competitive on the startline."
With the next "act" (cup pre-regatta) less than a month away, Pepper said the syndicate are eager to try out against the opposition. He is also looking forward to lining up against his old team and long-time friend Dean Barker.
"Team New Zealand are going to be good, Deano's not a bad match-racer," he laughs.
HAMISH PEPPER
* Born: Auckland May 13, 1971
* Educated: Westlake Boys High School
* Career highlights:
2005-2007: Mascalzone Latino
1995-2003: Team New Zealand
2004: Olympic Games - 7th in the Laser class
1998: Olympics Games - 10th in the Laser class
Yachting: 'Pepperoni' takes to Latino life
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