The British sailor, who is aiming for a record-breaking fifth Olympic sailing medal in the Finn dinghy class further west along the south coast of England at Weymouth in a month's time, seems unperturbed by the swell in the Solent and the possibility of injuring himself.
Ainslie, 35, has joined Eleonora from training at his Weymouth base to practice at the helm of the huge replica of an early 20th century racing machine called "Westward".
The huge steel hull and towering wooden masts, with a host of hands on deck to hoist and trim the billowing sails, are a world apart from Ainslie's 4.5-metre, state-of-the art fibreglass Finn.
The Round the Island Race, sponsored by one of Ainslie's main financial backers, JP Morgan Asset Management, is his last before he takes to the waters off Weymouth to defend the gold medals he won in the Finn in Athens and Beijing.
Handling the heavy wooden wheel of the 214 ton vessel in the blustery 20 knot winds tests even Ainslie, who has been bulking up his 1.85 metre frame to compete at the Olympic venue, where conditions could be equally blowy.
Ainslie spends hours in the gym building up muscle he needs to sail the intensely physical single-handed dinghy, something he says is the biggest challenge in his preparation.
"Fitness is a huge part of it. We are in the final weeks of preparation, which will taper off with a week to go," Ainslie said back on dry land at Cowes on the Isle of Wight.
Asked what the worst part of the training regime is for him, Ainslie replied: "I don't really like the protein shakes. It is hard to keep putting on weight."
At 93 kilograms, Ainslie is as heavy as he can be, but still some way short of bigger competitors in the Finn who are taller and weigh around 100 kilos.
Ainslie is going for his fourth consecutive gold at Weymouth, a record that would equal that of Denmark's Paul Elvstrom and set a new record for the number of medals won in the discipline. At his first Olympics in Atlanta in 1996, Ainslie took silver in the Laser class at the age of just 19, moving on to Laser gold at Sydney in 2000.
With huge expectations for him to succeed in front of his home crowd, Ainslie finds the best way of dealing with the pressure is to focus on his own preparation.
"I keep my focus on the sailing. You have to be properly prepared with fitness and equipment. Then it's a question of just going out there and racing.
“So far things are going well. The preparation is going well and it's just a question of keeping focused on that."
Whereas at Beijing, Athens, Sydney and Atlanta, Ainslie could isolate himself from the public gaze, the demands on him on home waters are much greater.
"I have to stop myself from thinking about it too much, just to keep myself relaxed."
But there is no question of Ainslie's determination to win.
"When you are obsessed with something it consumes your life. You have got to really want to do it. It's not great for relationships and marriage and everything," he says.
What happens beyond London 2012 is still undecided, although Ainslie thinks that even if he does compete in Rio in 2016 he probably won't be sailing in the Finn again.
"I honestly don't know. It depends on what the boats are in the next Olympics. It (the Finn) is unlikely, but never say never."
One option would be to move into the two-man Star class. That could potentially pit him against reigning Olympic champions Iain Percy, who won gold in the Finn in Sydney, and his crew Andrew Simpson.
"The Star would be a great challenge. But it would put me up against Ian and Bart (Simpson) and they are great mates of mine."
Another is a return to the America's Cup. Despite disappointments so far, he still has his eye on the "Auld Mug".
Ainslie has already signalled he will launch his own racing team to compete in yachting's blue riband event, which has been a long-held dream.
"It would be an amazing thing to win that," he says.
But for now his attention is on fulfilling national hopes and expectations.
Apart from local knowledge, the depth of talent among British Finn sailors will be one of Ainslie's main advantages when he takes to the water on July 29 for the first of 11 gruelling races to decide Olympic gold.
He was selected over current Finn world champion Giles Scott for the sole British place in the class and the sailor is one of five training partners Ainslie's coaching team are using to make sure that their medal favourite is at the top of his game in Weymouth.
"The training and testing group is awesome," says Mark Andrews, 26, another British Finn sailor who lost out to Ainslie but is now also a training partner and knows what it is like to compete against him. "We have five guys that are top 10 in the world all training together."
Andrews says Ainslie's time working with America's Cup teams -- firstly Team New Zealand and then the now disbanded British syndicate of Team Origin -- has helped the Briton redefine even his own high standards.
The contacts it has given him have also meant that Ainslie is better funded than other Finn sailors and he has been able to focus on developing his equipment.
But the extra backing has, if anything, made Ainslie even more of a perfectionist.
"Even when he is winning, nothing is perfect,” said Andrews, who thinks Ainslie should win, despite the tough competition.
“This time (at Weymouth) it's a bit closer, especially with the breeze, to the other guys. He spends a lot of hours on the water. The desire is definitely there."
"If you were a betting man, you would put your money on it. But Weymouth is not like San Francisco. You don't know what conditions you are going to get. He (Ainslie) has done the business in the past."
That confidence is shared by Ainslie's sponsors, who stuck with him after an out-of-character disqualification last year for an after-race altercation with a media boat.
"He knows what he wants to do and he goes out there to achieve it," said Jasper Berens, who is head of UK Funds at JP Morgan Asset Management.
"I'm convinced that in a month's time he will pick up that gold medal."
But for all Eleonora's majesty and Ainslie's ability, the largest boat in the fleet of 1,650 racing around the Isle of Wight, was not the weekend's winner.
Conditions were not in the schooner's favour and Ainslie will be hoping for more gentle breezes at the end of the month.
Ainslie's biggest fear, however, is not the sailing conditions at Weymouth, where he capsized in the last race of the recent Sail for Gold regatta, ending up second to training buddy Scott.
"My biggest nightmare is gear failure. The course is such a long way out, if something went wrong you would miss two races."