Entertainment

Inside Leonardo DiCaprio’s three month holiday – and all the young models he’s picked up en route

LEONARDO DiCAPRIO certainly knows how to holiday in style – he’s had plenty of practise in the past three months.

The 48-year-old playboy – and so-called eco warrior – has been criss-crossing the Med and the Atlantic to 17 destinations since May.

Leonardo DiCaprio in his trunks on board a superyacht in Italy in JuneCredit: BackGrid

Love Island beauty Arabella Chi and boyfriend Richie Akiva were on the actor’s party boat in IbizaCredit: Instagram

Model Irina Shayk was at Leo’s premiere in FranceCredit: Eroteme

While most of us are hard at work, it seems star of travelling adventure drama The Beach is making the most of some downtime during the writers’ strikes in Hollywood.

And Leo – famed for his love of Victoria’s Secret models and never publicly dating a woman over 25 – hasn’t been short of company.

Those who have joined him on his jaunts include a billionaire businessman, a disgraced art dealer and, of course, a bevy of beautiful young women, making many question if the former child star will ever grow up.

Emma Pietras tracks his holiday diary as he enjoys himself in France, Italy, Spain, the US and the UK.

Cannes

LEO jetted into the South of France for the Cannes Film Festival, which screened his latest movie, Killers Of The Flower Moon, directed by Martin Scorsese.

He was spotted relaxing with best pal and fellow A-List actor Tobey Maguire, 48, on board the yacht owned by Mariah Carey’s billionaire ex James Packer.

Leo with Robert de Niro, Martin Scorsese and Lily Gladstone at the Cannes Film FestivalCredit: Getty

Supermodel Irina Shayk was among those invited to the premiere of his movie, and the pair also reportedly hung out at Naomi Campbell’s birthday bash – but at 37, the Russian beauty is considerably older than his usual type.

Amalfi

IN mid-June, the Hollywood star headed to Italy’s Amalfi coast, where he enjoyed an al fresco lunch with dad George and step-mum Peggy in Naples.

Leo’s 16-year-old niece Normandie, who joined him on the family trip, was pictured sunbathing on a yacht in a strapless striped bikini.

The yacht is owned by Mariah Carey’s billionaire ex James PackerCredit: The Mega Agency

The actor also spent time in the fishing village of Nerano and soaked up the sunshine on board a superyacht.

Florence

FORMER Spider-Man actor Tobey Maguire and Leo were spotted enjoying a late-night stroll through Florence in mid-June.

The two friends were joined by Tobey’s ex-wife, 46-year-old jewellery designer Jennifer Meyer, and the former couple’s two teen children on a trip to the Italian city’s 18th-century historical park, Boboli Gardens.

Forte dei Marmi

CONTINUING his Italian odyssey, Leo tucked into an al fresco meal at Forte dei Marmi’s swanky seafood restaurant Maito in mid-June with step-mum Peggy and dad George.

Diners did not seem to recognise Leo, who kept a low profile in a black baseball cap, T-shirt and jeans.

British fashion model Neelam Gill and pals at Forte dei MarmiCredit: BackGridParis

BELGIAN model Rose Bertram has been romantically linked to Leo and the pair attended the GQ/Levi’s after-party at the Avenue restaurant, along with the Oscar-winner’s bestie Tobey Maguire, during Paris Fashion Week in June.

Later that evening they were joined by British catwalk star Neelam Gill, along with Tobey’s daughter Ruby, 16, his son Otis, 14, and Leo’s niece Normandie.

Rose Bertram has been romantically linked to LeoCredit: BackGridLondon

ON the first of four trips to London, Leo watched rapper Machine Gun Kelly at a private show in posh Mayfair, hosted by fashion designer Marc Jacques Burton.

He returned to the capital a short while later for a meal with his dad George and step-mum Peggy at celeb hotspot China Tang.

Leo and model Gigi Hadid both left China Tang within minutes of each otherCredit: The Mega Agency

And it seems it was a meet-the-parents date, as rumoured love interest Gigi Hadid was snapped arriving there later.

Afterwards, Leo and model Gigi, 28, both left the restaurant within minutes of each other.

Rumours that the pair were dating emerged last September, after Leo split up from his girlfriend, actress Camila Morrone, shortly after her 25th birthday.

In mid-July he partied with Maya Jama and model Neelam Gill, both 28, at the Love Island presenter’s Vogue Summer party.

At the end of last month Leo attended Sir Mick Jagger’s 80th birthday party at Chelsea nightspot Embargo Republica.

Saint-Tropez

MAKING quite an entrance, Leo arrived on a speedboat at Club 55 in celebrity hangout Saint-Tropez – flanked once again by his trusty wingman Tobey Maguire.

Leo was also snapped jumping off the top deck of a yacht into the Mediterranean in blue trunks.

Sardinia

IT wasn’t just the stunning scenery of the Italian island that was sure to catch Leonardo’s eye.

A mystery brunette, wearing a pink bikini that perfectly showcased her pert bottom, joined him on a yacht off the coast of Sardinia last month.

Bikini-clad Neelam Gill was snapped aboard the boatCredit: Splash

Also on board were Swiss businessman Ernesto Bertarelli, 57, and disgraced New York art dealer Hillel “Helly” Nahmad.

Nahmad, 46, spent five months in jail for operating an illegal gambling business, said to include celebrities, Wall Street bankers and professional athletes.

He was released from prison in 2014 and given a full pardon by President Trump in 2021.

Leo returned to Sardinia and was snapped holding the hand of a mystery brunette on board a yacht.

Also there was bikini-clad Neelam Gill.

A familiar face among his entourage on previous jaunts, the model was quick to quash rumours she was dating The Wolf Of Wall Street megastar.

Neelam wrote on Instagram that she was “in a committed relationship with his good friend” and the reason they have been pictured together is because she had attended the trips with her partner.

New York & Hamptons

BACK in the States last week, the globetrotting star was snapped hopping out of the passenger seat of a sporty convertible after going for a spin with some of his pals in New York.

Days later he arrived by helicopter at the super-smart Hamptons, on Long Island.

Fuelling rumours of yet another romance, a mystery woman wearing a black bralet underneath a leather bomber jacket was pictured with Leo on the runway.

Ibiza

ANOTHER sun-kissed isle and yet another striking woman on Leo’s yacht.

The beauty who joined him on this occasion was US model Meghan Roche, 22.

Megan Roche joined Leo on the yachtCredit: meghanroche/instagram

She wowed in a plunging dark blue swimming costume under a pair of low-rise jogging bottoms and unbuttoned shirt.

Leo returned to Ibiza, where he was this week joined by ex-Love Island contestant Arabella Chi, who is dating Leo’s long-time friend Richie Akiva, 45 – dubbed “the King of nightclubs”.

Influencer Arabella, 32, showed off her jaw-dropping figure in a gold string bikini while on Leo’s boat, which he is taking around the Med on an eight-week cruise.

Two beauties baord the boat to party with Leo and Tobey MaguireCredit: The Mega Agency

Related Posts

‘Goonies’ Sequel ‘Curse of One-Eyed Willy’ Is Releasing in Theaters in Summer 2026?

The 1985 classic film “The Goonies” was a hot topic of discussion on social media in early 2024, with users sharing news of a sequel title and poster….

QG Part 1 – (Hindi) Official Trailer | Vivek Kumar Kannan | Sunny Leone | Jackie Shroff | Priyamani

QG Part 1 – (Hindi) Official Trailer | Vivek Kumar Kannan | Sunny Leone | Jackie Shroff | Priyamani The plot centers around a mysterious protagonist who embarks…

Aranmanai 5 – Official Trailer | Sundar.C | Vijay sethupathi | Yogi babu | Hiphop Tamizha

“Aranmanai 5” is a cinematic masterpiece that opens up a world of mystery and suspense with its distinctive blend of supernatural and eerie elements. The story unfolds in…

CHUCKY vs M3GAN: Blumhouse Teases Epic Showdown in 2024

Blumhouse Productions has just released the highly anticipated teaser trailer for their upcoming 2024 horror crossover, CHUCKY vs M3GAN. The film brings together two of the most iconic…

The Boy 3: The Curse Continues – Official Trailer Released

The chilling new installment of The Boy franchise, titled The Boy 3: The Curse Continues, has finally unveiled its official trailer for 2024, and it promises to bring…

WINTER CHAINSAW MASSACRE | Teaser Trailer 2025 | Netflix

𝑁𝑒𝑡𝑓𝑙𝑖𝑥 ℎ𝑎𝑠 𝑗𝑢𝑠𝑡 𝑑𝑟𝑜𝑝𝑝𝑒𝑑 𝑡ℎ𝑒 𝑐ℎ𝑖𝑙𝑙𝑖𝑛𝑔 𝑡𝑒𝑎𝑠𝑒𝑟 𝑡𝑟𝑎𝑖𝑙𝑒𝑟 𝑓𝑜𝑟 𝑊𝑖𝑛𝑡𝑒𝑟 𝐶ℎ𝑎𝑖𝑛𝑠𝑎𝑤 𝑀𝑎𝑠𝑠𝑎𝑐𝑟𝑒 (2025), 𝑎 𝑓𝑟𝑒𝑠ℎ 𝑎𝑛𝑑 𝑖𝑐𝑦 𝑡𝑎𝑘𝑒 𝑜𝑛 𝑡ℎ𝑒 𝑖𝑛𝑓𝑎𝑚𝑜𝑢𝑠 𝐿𝑒𝑎𝑡ℎ𝑒𝑟𝑓𝑎𝑐𝑒. 𝑇ℎ𝑖𝑠 𝑤𝑖𝑛𝑡𝑒𝑟-𝑡ℎ𝑒𝑚𝑒𝑑 ℎ𝑜𝑟𝑟𝑜𝑟 𝑖𝑛𝑠𝑡𝑎𝑙𝑙𝑚𝑒𝑛𝑡 𝑠𝑒𝑡𝑠 𝑡ℎ𝑒…

Leave a Reply

Your email address will not be published. Required fields are marked *