From San Siro to Brera… Discover the Milan that Belonged to Ronaldo

In the summer of 1997 the city of Milan was buzzing. Inter had shattered the transfer record to bring the best player in the world to Serie A.

Ronaldo Nazario had spent the season before tearing LaLiga to shreds while at Barcelona, turning grizzled defenders into puddles of water with his devastating mix of speed, power and skill.

Inter president Massimo Moratti, a man never afraid to spend, liked what he saw and informed Barca he was ready to trigger his release clause. There was little the Catalans could do about it and it was the last time Serie A flexed its financial muscle and signed the world’s greatest.

The transfer sent a wave of excitement through Italian football not seen since Diego Maradona joined Napoli in the summer of 1984.

Ronaldo’s first season with Inter was his best: 34 goals in 47 games doesn’t begin to give a true reflection on how much he toyed with the game’s best defenders. 

He tortured the great Alessandro Nesta so badly in the 1998 UEFA Cup final against Lazio in Paris that the Italian struggled to get over it. “I have watched that game on video so many times since then, trying to work out what I did wrong,” he recalled. “We lost 3-0 but I don’t think it was my fault. Ronaldo was simply unstoppable.”

Such was Ronaldo’s aura that players wanted to join Inter to play alongside him. This was the case for Clarence Seedorf and Christian Vieri, with the latter often telling the story of his decision to move to Milan despite playing in a top Lazio side.

“When I joined Inter, I remember being in the dressing room as Ronaldo came in,” Vieri said. “I stood up, went to him and said, ‘I came here to play with you’. Sadly, we didn’t get to play much together.”

Even if they didn’t share a pitch often, Vieri and Ronaldo instantly hit it off, a friendship born out of enjoying life.

“We had a really good relationship, like best friends. We’d go out to restaurants in Milan. As we went in, all of the people would get up and applaud,” he added.

Vieri was particularly fond of Osteria del Corso on Via Corso Garibaldi. So fond that he told Destination Calcio last year he’s eaten lunch there “every day for 25 years”. Vieri stayed at the Nerazzurri for six years but remained in the city long after his career ended. 

Ronaldo’s stint in Milan wasn’t quite as long but his five years there were memorable. Milan is the fashion capital and Ronaldo was as marketable a sports star as there was in the late 1990s. Design week is when the city buzzes as hotels, high-end bars and restaurants are busier than normal and celebrities come out to play.

The next one takes place from Tuesday September 22-28 and the weekend just before, AC Milan are at home to Lecce while Monza, back in the top flight and less than 15 minutes away on the train, entertain Sassuolo. Tickets for San Siro and Monza’s U-Power Stadium are easy to come by if you get organised and book early.

Any visit to Milan isn’t complete without spending a day and night in Brera, a district known as the ‘Milanese Montmartre’. It is just north of Piazza del Duomo and has bars, cocktail venues and nightclubs. Osteria Formentini is perfect for a long lunch while Bar Jamaica is our recommendation for a nightcap.

One of Ronaldo’s favourite nightspots, Old Fashion, closed its doors in 2024 after 90 years, and these days the Inter players are known to socialise in Chinatown, slightly further north than Brera.

Like many of the stars who shone for Inter during the 1990s, Ronaldo was put up by the club in an apartment block overlooking San Siro. Most of the players had one apartment, but Ronaldo wasn’t just any player. According to Robbie Keane, who played for Inter briefly in 2000, Ronaldo had “not just the top floor, but three, including a room with a jacuzzi”.

After the initial success, Ronaldo suffered two major injuries while at Inter, with the second stopping his career for 18 months. He would leave for Real Madrid following the 2002 World Cup in Japan and South Korea after scoring the goals that brought the Selecao’s fifth world title. After four-and-a-half seasons at the Bernabeu he joined the list of players who have crossed the Milan divide, signing for the red-and-black half of San Siro.

Yet he loved his time in the city and with Inter, saying in 2018: “It’s a real love affair with the club, I was very comfortable in Milan and I’m so grateful for what Inter have done for me.”

Ronaldo’s playground during those years was of course San Siro, and one of football’s great cathedrals is on borrowed time, with plans afoot to demolish the stadium and build a new one in the coming years. Now is the time to start planning your visit.