THE MADGESTY COLLETION: 1987

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 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 after "I'm Going Bananas". She was dressed in a blue and white striped shirt while Nikki and Donna 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.

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 song, she was joined by her backup dancers who, along with Madonna, 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 2008–2009 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.

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.

La Isla Bonita debuted at number fifty-six and reached a peak of number four on the Billboard Hot 100 chart in March 1987.  In the United Kingdom, "La Isla Bonita" topped the UK Singles Chart for two weeks, giving Madonna her fourth number-one single on the chart.  The song also peaked atop the charts in France, Switzerland, Belgium and Austria along with reaching the top-five in Ireland, Italy, Netherlands, Norway and Sweden. 

La Isla Bonita was released as the fifth and final single from True Blue, True Blue, on February 25, 1987. "La Isla Bonita" was written by Patrick Leonard and Bruce Gaitsch. The song was previously written as a lament for the mythical Spanish island called San Pedro and was offered to Michael Jackson for his Bad album, who, according to Gaitsch, turned it down. While working with Leonard on the True Blue album, Madonna accepted it in Jackson's place and re-wrote the song's lyrics, thus earning herself a co-writing credit. The song was the first Madonna song to employ Spanish motifs, going so far as to include Spanish lyrics.

Madonna described the song as her tribute to the "beauty and mystery of Latin American people". According to her "Latin rhythms often dominate our uptempo compositions. It's like we're possessed. We both think that we were Latin in another life."

"La Isla Bonita" is noted for being the first Madonna song to have a Spanish influence in it with arrangements of Cuban drums and Spanish guitar, maracas, harmonicas and a mix of synthesized and real drumming. The lyrics of the song tell about a ‘Beautiful Island’ and was a tribute to the beauty of the Latin people according to Madonna.

"La Isla Bonita" achieved worldwide popularity, topping charts in countries such as Austria, Canada, France, Germany and Switzerland. It became Madonna's fourth number-one single in the United Kingdom, giving her a record for most number-one singles among female artists. In the United States, it reached number four on the Billboard Hot 100 chart.  In the accompanying music video, Madonna portrayed two opposite characters – a pious girl and a passionate Latina. The Latin style and the flamenco red dress she wore became a trend later. The song is among one of the most performed live songs by Madonna, appearing in five of her world tours. Madonna has regularly performed the song in its Spanish form, sometimes with tribal or folk songs and remixes to accompany it.  The video world-premiered on MTV on March 6, 1987, set in Los Angeles and was directed by Mary Lambert.  Actor, Benicio del Toro appeared in the video as a background character.