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Madonna was seen holding hands with her new boyfriend Akeem Morris - who is 37 years younger than her.
The pop icon, 65, held on to 28-year-old Akeem's arm as they were seen taking in the sites in Portofino, Italy.
Akeem, who is a Jamaican born-soccer player, was on her August 2022 Paper magazine cover shoot with her.
The lovebirds are in Italy ahead of Madonna's 66th birthday - which is August 16.
Their sighting comes just over a month after he spent the Fourth of July with her, which she shared to her Instagram page.
Madonna was seen holding hands with her new boyfriend Akeem Morris - who is 37 years younger than her
The pop icon, 65, held on to 28-year-old Akeem's arm as they were seen taking in the sites in Portofino, Italy
Madonna looked lovely in a black gown, which featured a solid black thigh-length dress layered with a dramatic lace overlay that reached her ankles and had a cape.
She added layers of necklaces, including a cross as well as multiple bracelets.
Madonna walked on the cobblestone streets in slip on sandals with her blonde locks in slight waves around her.
The icon wore black lace gloves and sunglasses to round out her look.
She held on to Akeem's forearm as they made their way around the historical city.
The two were all smiles as they walked hand-in-hand
Akeem was every bit the gent as he led the way on the cobblestones
The lovebirds are in Italy ahead of Madonna's 66th birthday - which is August 16.
She added layers of necklaces, including a cross
Madonna looked lovely in a black gown, which featured a solid black thigh-length dress layered with a dramatic lace overlay that reached her ankles and had a cape
Madonna walked on the cobblestone streets in slip on sandals with her blonde locks in slight waves around her
Madonna seen holding on to Akeem's arm for their Tuesday outing
Madonna seen with her friends and family, which also include twin daughters Stella and Estere, 11
Akeem wore a knitted top with black and white shorts
Akeem cut a casual figure in a green collared knitted top with white shorts, adding sunglasses.
The couple later went and sat down to enjoy an al fresco lunch with friends.
Madonna and Akeem appeared to have first met in 2022 - he appeared on her August 2022 cover issue of Paper Magazine.
He is a Jamaican born soccer paper.
They were first pictured together on her Instagram page.
On the fourth of July, Madonna shared a raunchy slideshow of pictures featuring her and Akeem racy poses, including one where his hand sits atop her cleavage as they lay on a couch together.
The couple later went and sat down to enjoy an al fresco lunch with friends
Madonna beamed alongside her boyfriend as they walked toward the restaurant
Madonna listened attentively to her boyfriend as they chatted on the way to lunch
She kept a tight hold on her boyfriend's arm
Madonna looked absolutely smitten
Madonna looked impossibly youthful and her signature blonde hair was left down
The A-list fashionista carried an antique umbrella and sported black mesh gloves
The lovebirds looked relaxed despite the fanfare
Madonna wowed in head-to-toe Dolce & Gabbana
The couple enjoyed an al fresco lunch
She kept sunglasses on as they made their way to the restaurant for lunch
Madonna and her entourage also stopped to shop
She wrote: 'Happy 4th of July! A year ago today, I had just come home from the hospital after surviving a life threatening illness, I could barely stand in my backyard holding one sparkler.
'I made a miraculous recovery and had an amazing year. Thank you God. Life is beautiful!'
The images included were of Akeem and Madonna is racy poses together while spending time on the Fourth of July.
Just one week prior, Madonna shared another steamy image of her and Akeem.
Madonna shocked once again as she went topless in a steamy set of snaps posted on social media including a steamy one of her sitting on the lap of her new toyboy lover.
She cheekily captioned the post to her 20million fans: 'Hot Fun in The Summer Time……… [fire emoji]'
Despite her being topless no doubt the thing that will get tongues wagging was one of the snaps which featured her on top of the hunky new boytoy who posed with a smile right behind her.
The megastar took to Instagram to share a gallery of snaps as she showcased her bare chest behind her blonde locks.
The only thing Madonna had on were several diamond-encrusted platinum necklaces featuring varying sized pendants including crosses and a New York Yankees logo.
Madonna shared a raunchy slideshow of pictures featuring her and Akeem racy poses, including one where his hand sits atop her cleavage as they lay on a couch together
They were first pictured together on her Instagram page
The star looked cozy as she posed up with her companion
Madonna shocked once again as she went topless in a steamy set of snaps posted on social media including a steamy one of her sitting on the lap of her new toyboy lover
The 65-year-old megastar took to Instagram to share a gallery of snaps as she showcased her bare chest behind her blonde locks
The Celebration Tour was initially set to begin on July 15, 2023 in Vancouver, Canada, but was postponed and pushed back three months after the pop icon developed a 'serious bacterial infection' in late June 2023, which led to a multiple-day stay at the intensive care unit (ICU).
Her first-ever career retrospective ended up kicking off with a four night run at London's O2 Arena beginning on October 14, and went through Europe until early December.
During a previous tour date in Brooklyn in December, the dance music pioneer joked that she had to 'almost die to get all my kids in one room.'
She shares 27-year-old daughter Lourdes with her former boyfriend and fitness trainer Carlos Leon and her 23-year-old son Rocco with her ex-husband, filmmaker Guy Ritchie.
Madonna later adopted her son David Banda, 18; daughter Chifundo 'Mercy' James, 18; and twin daughters Stella and Estere, 11.
The pop icon was rushed to hospital in June 2023 after being found unresponsive as the result of what was later determined to be a serious bacterial infection.
The songstress was taken to the ICU and had to be intubated, and she later revealed that she was put into a medically induced coma as she battled for her life despite going into lung and kidney failure.
She suffered an acute septic shock on June 24, 2023 according to Radar Online, and emergency responders were reportedly able to revive her with Narcan.
The substance is traditionally used to treat people in the midst of opioid overdoses, but it can also help revive someone suffering from septic shock.
At her Brooklyn show, Madonna said her 'lungs weren't working' and her 'kidneys were failing,' and she claimed there was a 40 percent chance that she would not survive.
The tour then shifted to the U.S. and Canada beginning with shows at Barclays Center in Brooklyn, New York that went around North America until mid-April when she headed to Mexico City for five concerts.
Ultimately, the Celebration Tour ended on May 4 with a massive free concert at Rio de Janeiro's Copacabana Beach that attracted a whopping 1.6 million fans, which is now considered the biggest standalone concert of all time, according to the Economic Times.