In 2013 Santos released his second studio album My Way. Hits such as ' Poquito A Poquito', 'Por Amor (Mi Fiel Fanatica)' and ' Por Nada' were favorites among worldwide bachata listeners. It debuted at number 2 on the Billboard Tropical Albums Chart. In 2011, Santos released his debut solo album, ' Introducing Henry Santos'. Their last 2 shows together were On December 18th and 19th, 2021 in Dominican Republic. The last concert of the tour was on October 9th, 2021 at Metlife Stadium in New Jersey. They eventually would return in 2021 in which they did many Stadium shows in the United States. Shows were cancelled and the group wasn’t able to finish the tour. From February to March 2020, Aventura tour around the United States until the Covid 19 Pandemic. Later that year they had announced the Inmortal Tour.

2019, he reunited again with the group at his cousin Romeo Santos' sold out concert at MetLife Stadium to close the show. On February 4, 2016, Henry Santos would reunite with Aventura for a 21-day concert series at the United Palace in New York City. First time it happened on July 12, 2014, 3 Years after the split, he reunited with his old bandmates Lenny, Max & Anthony in a surprise reunion of Aventura during Romeo Santos' historic sold out concert at Yankee Stadium. Santos would eventually have multiple reunions with his group over the years. Later that year, Henry Santos & Romeo released solo albums.

After nine albums (six studio and three live efforts) Aventura announced their separation in 2011. It was the first of ten straight top ten hits on the Billboard Hot Latin Songs chart. Aventura's success was elevated by 'Ella Y Yo', a collaboration with the reggaeton artist Don Omar from their fifth Studio album God's Project (2005). Aventura became recognized worldwide with the smash hit 'Obsesión' from their third album, We Broke The Rules (2002). Originally known as 'Los Tinellers', the group made its full-length debut with “ Trampa De Amor” in 1995.

He and Anthony 'Romeo' Santos have written several hits for the band such as 'Deja Vu', 'Voy Mal Acostumbrado', '9:15' and 'Princesita'. Santos was a singer, songwriter, and producer for the band.

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