The pair flew to Miami, Florida, on Monday night, the source adds, where Drake has scheduled shows at the AmericanAirlines Arena on Tuesday and Wednesday night as part of his Summer Sixteen Tour.
Drake, 29, and Rihanna, 28, have definitely been spending plenty of quality time together recently. On Monday night, prior to their flight, the superstars stepped out for a dinner date at Nobu in New York City. An eyewitness tells ET that Rihanna stayed at Drake’s hotel overnight on Sunday after winning the Michael Jackson Video Vanguard Award at the MTV Video Music Awards.
The "Hotline Bling" rapper boldly declared his love for Rihanna onstage at the VMAs on Sunday, when he showed up at the end of the show to present her with the big award. He also touched on their longtime friendship.
"The first time I met Robyn Fenty was in 2005," he shared, recalling Rihanna's very first music video shoot for "Pon de Replay" in his native Toronto. "I was introduced to her as the kid who played background music at the restaurant as people ate their dinner."
"She's someone I've been in love with since I was 22 years old," he later gushed, prompting big cheers from the audience. "She's one of my best friends in the world. All my adult life, I've looked up to her, even though she's younger than me. She's a living, breathing legend in our industry."
And the flirtiness between the two didn't stop there. Drake -- who also bought a billboard sign for Rihanna ahead of her MTV honor and later shared a kissing selfie of the two -- only had eyes for the "Love On the Brain" singer at a VMA after-party at Up & Down nightclub, a source told ET.
"They walked in together and never left each other's side all night," the source said. "He was so attentive to her. His eyes were never off her. They were necking a lot. They would hug and he would kiss into her neck."