Aventura released five studio albums in a decade, creating many top 10 hits like "Cuándo Volverás", "Un Beso", "Mi Corazoncito", "Los Infieles", "El Perdedor", "Por un Segundo", "Dile al Amor", among others.
These four would form Los Tinellers, which is the word 'teenagers' but spelled in Spanish letters so non-English speaking Hispanics could pronounce it.
On November 9, 1999, they released their debut album Generation Next along with a modernized and better known version of "Cuándo Volverás" as its main single in hopes of breaking bachata music into the mainstream from its traditional base.
[8] They slowly began to gather fans in Dominican Republic and in the east coast of the United States, especially in the cities of New York, Boston and Lancaster.
The group was the first to experiment with fusing bachata with other genres like R&B, Pop, Hip Hop, Rap, Reggae and Rock.
While the album did have some success, it didn't exceed expectations as the group was heavily criticized about the new style and the fact that they had added English in to the genre.
The songs were "Todavía Me Amas", "Amor De Madre", "Enséñame A Olvidar", and "Obsesión" which featured Dominican-American singer Judy Santos.
This led the group and the record label to make the decision to have Anthony go under the name he is known today, Romeo Santos.
The album would feature Judy Santos and Puerto Rican-American singer Toby Love, who worked for them as a back up vocalist until he left in 2005 to pursue a solo career.
It was the best-selling tropical album of 2006 in the United States and was certified 4× Platinum in the U.S. by the Recording Industry Association of America (RIAA).
The concert featured artists like Don Omar, Anthony Santos, Wisin & Yandel, Miri Ben-Ari, Toby Love, and Héctor Acosta.
On November 13, 2007, they would release their third live album and third concert film, Kings of Bachata: Sold Out at Madison Square Garden.
In December 2008, the band would sell out 5 night at the José Miguel Agrelot Coliseum in San Juan, Puerto Rico from the 4th to the 7th, and the 10th of that month.
On the same day, Aventura was invited to perform their hit single "Su Veneno" at the White House for the 44th President of the United States, Barack Obama.
[23] On October 15, 2009, it air on television as part of the "Fiesta Latina" episode of the TV series, In Performance at the White House.
[24] In early 2010, they sold out Madison Square Garden once again, but for a legendary four nights in a row at part of The Last Tour.
[10] At one of the concerts they paid homage to Juan Luis Guerra, and even sang some songs with the iconic Dominican singer.
On February 13, 2010, the group would perform at the Félix Sánchez Olympic Stadium in Santo Domingo, Dominican Republic in front of a crowd of about 50,000 to 60,000 people.
[27] From the 3rd to the 5th December 2010, the group performed for three nights at the José Miguel Agrelot Coliseum in San Juan, Puerto Rico.
Although Max wanted to focus more on his rap career, he joined his brother Lenny and formed their new bachata group called "D'Element."
At the same time, Max Santos worked alongside many dembow artists and also focused on his solo career as a rapper.
On December 1, 2015, it was announced on the band's website and social media that they would have a reunion tour for the whole month of February at the United Palace theater in New York City.
As for Lenny, he would form a new duo called DNA Latin Group with a singer by the name of J Love and released 2 singles together.
On April 1, 2019, the group posted an image on their Instagram account teasing a new Aventura single called "Inmortal" slated to be released at 9PM, captioning it "#UTOPIA".
[35] At 9PM, Romeo uploaded a video saying that their new song would not be released at 9PM after all, and that it was intended to be an April Fool's joke which led the fans to become upset and lash out on social media.
They then previewed the new single "Inmortal" and its music video, stating that it was being released on April 5, as a part of Romeo's fourth studio and first collaboration album, Utopia.
But instead of doing the shows in the venues that were originally planned before their cancelation, they decided to play at stadiums and big arenas in certain cities.
[49] On November 4, 2021, Aventura announced their very last concert to be set for December 18, 2021, At the Félix Sánchez Olympic Stadium in Santo Domingo, Dominican Republic.
As for Lenny and Max, they would have these special events tour where they would play Aventura hits in clubs and small venues.
The group's musical style led to them being pioneers in creating the Urban Bachata sound, having inspired artists like Prince Royce, Leslie Grace, among others.