The cute couple was also seen enjoying water-based sports during the outing.
The duo was seen dining at New York's Beatrice Inn this weekend.
The Grammy-winner had even posted a series of pictures from their night-out on his Instagram account.
Rihanna and A$AP Rocky sparked dating speculations after they were spotted getting close during a night out in New York City.
The two musicians were spotted standing next to each other in the crowd as they watched one of the performances at Yams Day 2020.
The couple are yet to confirm the news.
Drake's equation with the make-up mogul is more complicated than it appears, as he reportedly "always had a thing for Kylie."
The rumours started surfacing after Kylie was spotted getting cozy with the 33-year-old rapper at his mobster-themed birthday party in LA.
Kylie Jenner and Drake spent a lot of time together on his birthday party.
Drake and several members of his OVO crew headed to a nightclub for a fun night out and RiRi also showed up.
Hip-hop star also donated $25k to Miami Senior High School, where his God's Plan music video is set.
The One Dance singer was reportedly spotted 'flirting' with 44-year-old Kelly Price in Houston, accordig to a new report.
The incident is said to have occurred at the Marquee nightclub after Drake wrapped up his concert at the Qudos Bank Arena in Sydney.
Apple will give Drizzy a blank cheque to produce original TV and film content for its streaming service, Apple Music.
Rihanna looks typically glamorous in the November issue of the glossy magazine.
"The Weeknd doesn't want Drake dating Bella Hadid if the latter is going to continue being a player."
Drake is said to be worried about losing RiRi forever even though he "always tries to stay friends with his exes".
Although Bella Hadid is said to have a crush on Drake, "her sister and other friends have warned" her about the singer's "player" ways.
Young Money star considers Houston his home away from home.
Drake performed annual music concert alongside Tory Lanez and French Montana on 7 August.
Dennis Graham is an R'n'B singer in his own right and gives his famous rapper son a run for his money.
Rappers have been friends for nearly 10 years after Lil Wayne signed Drake to YMCMB.