Red Bull's gritty Australian racer has won the most glamorous event on the Formula One calendar twice in the last three years and counts doing so as one of the greatest thrills of his career.
The great outdoors remains his favourite surroundings, however, and unlike most other drivers he has shunned the Mediterranean millionaires' and tax exiles' playground for a more normal life with his dogs and partner in the English countryside.
"I think these guys if they had a choice they probably wouldn't be living here," he said of his rivals as he gestured out of the floating Red Bull hospitality centre, moored to the Monaco quayside.
"I think it's a very dramatic backdrop, I love the ocean and I love the cliff faces. To have a race track here is quite exceptional.
"But for me, in terms of all the small dogs and the handbags and that sort of stuff, it's not really my thing mate."
Webber won from pole position in 2010 and 2012, with team mate and triple champion Sebastian Vettel - who lives in Switzerland - taking the victory for Red Bull in 2011.
The Australian leaped into the somewhat murky harbour after that first win and can be expected to perform backflips into the swimming pool on the deck of the team's 'energy centre' if he gets to collect another trophy from Prince Albert on Sunday.
Webber has yet to win a race this season, thwarted in Malaysia when Vettel defied team orders and overtook him, but Monaco represents a real chance to take his career tally of wins into double figures.
"It's been good to me, mate. Long may it continue," he smiled.
"We've got another chance this weekend, which is exciting. I grew up on street circuits in Australia; Adelaide with Formula Ford, Surfers's Paradise. So from a young age I was used to having the barriers pretty close."
Monaco, Brazil and Silverstone are all races Webber has won twice with his other victories achieved in Hungary, Spain and Germany.
The Mediterranean street circuit, with its metal fences and tight turns, can be treacherous and unforgiving but Webber would rather that to the modern purpose-built layouts with vast runoffs where drivers can make big errors and go unpunished.
"The margin is very small here...it's different to Bahrain where it's impossible to crash a car," he said.
"But here you can, so you need to be very mentally aware of that and on top of it and be disciplined over the course of the weekend as best you can."
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