With its crumbling concrete highways, communist graffiti and dockyards stacked high with containers, Naples is a raw kind of city for a team in desperate need of a win and a young manager who cannot catch a break.
If Andre Villas-Boas had one immediate wish other than a solid victory against Napoli tonight it would surely be that people would stop asking him whether he thought he was about to lose his job.
On that subject there was a firm response from Villas-Boas last night and he had Didier Drogba, his most important player, alongside him as a show of solidarity. Villas-Boas conceded that nothing he can say will placate those of us who have seen Roman Abramovich depose a manager with such breathtaking suddenness, and in the absence of any other voice from Chelsea we will have to take his word for it.
The chief executive, Ron Gourlay, and chairman, Bruce Buck, were in the cramped San Paolo press room to listen to more questions about Villas-Boas's future and may well have sympathised in private with their manager but it is also pointless for them to make promises they cannot keep.
"These words would be more valuable coming from the top to you guys, I know," Villas-Boas said. "I cannot keep saying them, but as the voice of the club, I will continue to perpetuate this message because this is what we believe in."
For Villas-Boas, this Champions League knockout round first leg comes at a critical moment. His team have won just one of their last six matches in all competitions. He has had Abramovich breathing down his neck at the training ground the week before last. When he brought on Frank Lampard against Birmingham City in the FA Cup on Saturday, the veteran midfielder could barely bring himself to look at his manager.
If there is a hope for Villas-Boas it is that the hostility that his team are sure to encounter tonight will bring them together. Certainly, the racist abuse of the black players in his squad while they ate their lunch on the first floor of the Grand Hotel Vesuvio on the seafront yesterday was an appalling taste of what is likely to await them.
The San Paolo stadium is an atmospheric, if brutalist, concrete edifice and if the monkey chants continue tonight, no one will come away with fond memories. Yet big nights such as these tend to bring the best out of Chelsea, such as the occasion in November they beat Valencia 3-0 at home in the Champions League and won their group while the two Manchester clubs stumbled.
Drogba was at the press conference last night to defuse the controversy over whether he had given the team talk during Saturday's FA Cup tie, a charge he denied. "We'll have to be clever and we're going to do what the manager is going to ask us to do," he said at the end of his final answer. "Like always, of course." There was laughter between manager and player, albeit somewhat awkward.
Drogba had said earlier: "I want to make things clear: the manager made a speech at half-time, and after that, I think he's got some leaders in the team, in the squad. So we're here to help him. So, after that, we were trying to [help the team] win. At half-time. Nothing more. We did what the manager wanted us to do and tried to apply what he was saying. Nothing more. People are making a big thing out of nothing."
A good result tonight would take the pressure off Villas-Boas and give him the breathing space he so badly needs to put together a run in the Premier League that might take his team above Arsenal in fourth place. After tonight's first leg they play Bolton and Stoke at home either side of a trip to West Bromwich Albion before the return leg against Napoli. But first they have to get out of San Paolo alive.
It was there in November that Napoli beat Manchester City 2-1 and they are unbeaten for the last 11 European ties they have played at home. Their Serie A form has improved with two wins since Siena knocked them out the Coppa Italia earlier this month. The bookmakers make them favourites tonight. This is a major test for Villas-Boas, but it is supposed to be the kind of games he was brought in to win.
There were more suggestions yesterday, which may, of course, be nothing more than idle rumour, that Marcelo Bielsa, of Athletic Bilbao, is a possible alternative to Chelsea's manager. Villas-Boas will have to learn to put up with this if he is to have any longevity at his club. He was adamant yesterday that he is there for the long term.
He said: "You have to understand that this club, from 2004 up to now, has made a dramatic change for the best in terms of their past. It's the richest part of Chelsea's history, full of trophies and success, and you want to perpetuate that. To do that, you have to sometimes make changes because you cannot sustain the same habits you had in 2004, when this environment and team was created to make a winning team."
This time last year his Porto team won home and away against Seville in the round of 32 in the Europa League. Porto under Villas-Boas won home and away against CSKA Moscow in the next round. They scored five goals home and away against Spartak Moscow in the quarter-finals. They scored five goals at home to Villarreal in the semi-final and narrowly lost the away leg. Villas-Boas's record in the knockout rounds of European football is excellent.
Then the pressure was nothing like it is now although, in spite of all that, Villas-Boas was assertive last night. "There's full belief from the owner in what we're doing so, hopefully, it will continue to be just that," he said, although life would get a lot easier if they fly back to London in control of this tie.