Hamburg had once been Germany's main seaport, the fourth largest in the world, but in 1943 virtually the entire city had been reduced to rubble by World War II bombing raids. By 1960, when they arrived, the Hamburg that had grown up from the ruins of WWII had established its reputation throughout Europe as a city of vice and criminal activity. In contrast to an economically depressed post-war Liverpool, Hamburg was a wealthy city.
Williams, a 29-year-old Liverpool businessman and promoter, had sent his leading group, Derry and the Seniors (later known as Howie Casey and the Seniors) to Hamburg, where they were enjoying success, and wanted to send an additional group. He initially tried to send Rory Storm and the Hurricanes, but Storm and his group were committed to a Butlins holiday camp and turned Williams' offer down, as did Gerry and the Pacemakers. Williams started promoting concerts for The Beatles in May 1960, after they had played at his Jacaranda club in Liverpool, and offered The Beatles the Hamburg bookings. He booked them into Bruno Koschmider's Indra club in Hamburg for a season of bookings starting on 12 August 1960, but said that he was not impressed with them as a musical group, and hoped to find a better act to follow them.
As they had no permanent drummer, McCartney looked for someone to fill the Hamburg position, which was difficult, as Lennon later said that drummers were "few and far between", because a set of drums was an expensive item. Harrison had seen Best playing with the Black Jacks in The Casbah Coffee Club (which was run by his mother, Mona Best). He was regarded as a steady drummer, playing the bass drum on all four beats in the bar, which pushed the rhythm, and was known in Liverpool at the time as being "mean, moody, and magnificent" by female fans, which convinced McCartney he would be good for the group. After the Black Jacks broke up, McCartney asked Best to go to Hamburg, telling him they would earn £15 per week each. Best had the chance to go to a teacher-training college, as he had passed his school exams—unlike Lennon, McCartney and Harrison, who had failed most of theirs—but decided that playing in Hamburg would be a better career move.
The St. Pauli quarter of Hamburg, where the Indra club was located, was well known as an area where prostitutes were to be found, and was a dangerous place for anyone that looked different from the usual clientele. McCartney's father, Jim McCartney, was reluctant to let his teenage son go to Hamburg, but relented after a visit from Williams, who told him that he "shouldn't worry". Lennon's aunt, Mimi Smith, was also reluctant to allow Lennon to go to Hamburg, wanting Lennon to continue his studies, but Lennon placated her by exaggerating the amount he would earn. Best had an audition in Williams' Jacaranda club on 15 August 1960, and travelled to Hamburg the next day as a member of the group. Williams later admitted that the audition with Best was not needed, as they had not found any other drummer willing to travel to Hamburg, but did not tell Best in case he asked for more money. The group were to be paid about £100 per week, which was much more than promoters in Liverpool paid. Williams drove the group and their equipment in his Austin J4 minibus which was loaded by crane onto a ferry at Harwich on 16 August 1960, and landed at the Hook of Holland.
All five Beatles, Williams and his wife Beryl, her brother Barry Chang, and "Lord Woodbine" were in the minivan, along with Georg Sterner (Koschmider's translator and future waiter), making a total of ten people, which resulted in a journey that was both uncomfortable and dangerous. As Williams had not obtained work permits for West Germany, they were detained at Harwich for five hours. Williams finally convinced the authorities that they were students on holiday, although work permits were later obtained after their arrival in Hamburg. Note: 'Lord Woodbine' and Williams ran a Strip Club called New Cabaret Artistes club at 174a Upper Parliament Street, Liverpool. Lennon, McCartney, Harrison and Sutcliffe once played backing music for "Janice the Stripper" there, in July 1960.