Live Performances
Madonna has performed "La Isla Bonita" on most of her world tours including the 1987 Who's That Girl World Tour, the 1993 Girlie Show World Tour, the 2001 Drowned World Tour, the 2006 Confessions Tour, and in the Sticky & Sweet Tour in 2008–09. She also sang it at the 2007 Live Earth benefit concert in London.
In the Who's That Girl tour, "La Isla Bonita" was performed as a part of the encore. Madonna came out on the stage in a bright red flamenco dress like the video and performed the song, assisted by her backup singers Niki Haris, Donna De Lory and Debra Parson. A Latino dancing with Angel Ferreira was also included. Two different performances of the song on this tour can be found on the videos: Who's That Girl – Live in Japan, filmed in Tokyo, Japan, on June 22, 1987, and Ciao, Italia! – Live from Italy, filmed in Turin, Italy, on September 4, 1987. In the 1993 Girlie Show tour Madonna performed the song on top of a rising platform, after "I'm Going Bananas". She was dressed in a blue and white striped shirt while Haris and De Lory wore a similar outfit, but in black and red. One of the musicians walked around bare chest playing the acoustic guitar. During her 2001 Drowned World Tour, Madonna performed "La Isla Bonita" in the Latin segment of the show, wearing a revealing black senorita's dress and trousers, hair tied back and playing a Spanish guitar. She asked the crowd to join her while singing "olé ola" with the song.
Madonna performed "La Isla Bonita" during the Live Earth benefit concert where she was joined by members of gypsy punk band Gogol Bordello for a crazed hoedown version of the song. Gogol Bordello had previously joined her on the 2006 Confessions Tour where the song was played as a dance/tribal remix with interventions from Eugene Hütz and Sergey Ryabtsev from Gogol Bordello. In the Confessions Tour, Madonna appeared on the stage in a purple white leotard with open hair and started singing the song. In the middle of the performance, she was joined by her backup dancers who, along with the singer, walked the length of the stage singing the chorus. The performance ends with Madonna lying down on the stage. The video backdrops showed a tropical paradise like the island San Pedro mentioned in the song.
The song was once again added to the set list of her 2008–09 Sticky & Sweet Tour, as part of the Gypsy segment of the show, featuring the Arkady Gips band and the Romani-Gypsy folk song "Lela Pala Tute." The performance had Madonna wearing a short black skintight dress and knee-high boots with pink fluorescent beads and necklaces. Along with "Lela Pala Tute", there was a Mediterranean Street party with Greek dancing, another gypsy song called "Doli, Doli" and a flamenco solo performance.
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