Once upon a time it was only sailors who had a girl in every port, but Leonardo DiCaprio has somehow managed to readdress the old cliché during a seemingly never-ending summer break.
Arguably more familiar with top-knots than those of the nautical variety, the actor has spent more time on the ocean than your average Commodore while visiting some of Europe’s hottest holiday destinations – and he’s had some attractive company to boot, every sea-faring step of the way.
From Russian catwalk legends and American models to British fashionistas and an unlikely association with a former Love Island contestant – Leo’s growing entourage has been nothing if not rich, varied and occasionally unexpected.
But who exactly has partied with the Oscar-winner board his lavish love boat? And where has it been during what appears to be the holiday to end all holidays?
It’s a tough life: Leonardo DiCaprio has been on a seemingly never-ending summer break since May – and it doesn’t appear to be ending any time soon (pictured in Saint Tropez)
Setting sail: The actor’s yacht as spent the entire summer cruising Mediterranean waters from the south of France to southern Italy and Spain
1. CANNES – MAY
Ironically it all began on dry land, when Leo made a promotional appearance at the 76th annual Cannes Film Festival.
Accompanied by his peers, among them celebrated director Martin Scorsese, the actor was on hand to celebrate the launch of their forthcoming movie – the eagerly anticipated Killers Of The Flower Moon.
But what started as a work commitment soon turned into a busman’s holiday as Leo swapped the red carpet for the lower-deck of billionaire James Packer’s yacht.
Accompanied by close friend Tobey Maguire, the actor hung-out with Russian model Irina Shayk, the rumoured girlfriend of former NFL star Tom Brady.
He even found time for a separate appearance at British supermodel Naomi Campbell’s 53rd birthday celebration in the French resort town.
But for Leo, the party was only just getting started…
Main man: Ironically it all began on dry land, when Leo made a promotional appearance at the 76th annual Cannes Film Festival with Martin Scorsese (centre) and Robert De Niro (right)
Pals: While in Cannes the actor hung-out with Russian model Irina Shayk (L) and attended British supermodel Naomi Campbell’s 53rd birthday celebration (R)
Here we go: But what started as a work commitment soon turned into a holiday as Leo swapped the red carpet for the lower-deck of billionaire James Packer’s yacht, where he was joined by best friend Tobey Maguire
2. AMALFI COAST – JUNE
Within days the actor had moved on to Italy’s Amalfi Coast, where he was joined by father George and step-mother Peggy for a dinner date in Naples.
However he would soon be back aboard his yacht, moored off the Italian coast, for a sun-bathing session with 15-year old niece Normandie.
During return visits to southern Italy the shirtless star was seen unwinding off the Sorrento Coast – a short distance from picturesque fishing village Nerano.
Family holiday: In June the actor was joined by father George and step-mother Peggy for a dinner date in Naples
3. FLORENCE – JUNE
A thirst for culture and history saw Leo return to dry land, if only for a fleeting trip to the city of Florence in central Italy.
The actor paid a visit to its historic Medici Chapel with his family, before reuniting with old pal Tobey Maguire, Maguire’s ex-wife Jennifer Meyer and the former couple’s children, daughter Ruby, 16, and son Otis, 14.
Eschewing his A-list status, Leo and his extended group were seen waiting in line with other paying tourists while visiting the city’s Boboli Gardens.
Later that night he and Maguire joined a larger entourage of friends for a walk through the city’s Piazza della Signoria.
Night out: A thirst for culture and history saw Leo return to dry land, if only for a fleeting trip to the city of Florence in central Italy
Family: Next stop Tuscany and a dinner date with family at popular seafront restaurant Maitó in Italian coastal town Forte Dei Marmi
4. FORTE DEI MARMI – JUNE
Next stop Tuscany and a dinner date with family at popular seafront restaurant Maitó in Italian coastal town Forte Dei Marmi.
Famed for its seafood and wood-fired pizza, the venue welcomed Leo and his loved one at an al fresco table with prime views of the sweeping coastline.
The Oscar-winner kept a low profile for the meal, with a baseball cap pulled low over his head ensuring the public appearance slipped well under the radar of his fellow diners.
Stunning: With fashion week underway in the French capital, jet-setting Leo used the event as an opportunity to reunite with model Rose Bertram (pictured on the night)
Party time: During the same trip he attended a late night dinner at Loulou on the Rue de Rivoli with British model Neelan Gill (second right) and her boyfriend
5. PARIS – JUNE
With fashion week underway in the French capital, jet-setting Leo used the event as an opportunity to reunite with model Rose Bertram.
The actor has been romantically linked to Belgian model Bertram since March, and their joint appearance at Parisian restaurant L’Avenue did little to quell those rumours – not least because of his latest attempt to slip past unnoticed.
Leo had been attending a party hosted by men’s magazine GQ and fashion brand Levi’s at the venue, before he and Bertram made surreptitious separate exits later that night.
The actor was joined by best pal Maguire as he sauntered past with an obligatory cap shielding his features.
During the same trip he was seen leaving Hôtel Costes in the city’s 1st Arrondissement before attending a late night dinner at Loulou on the Rue de Rivoli with British model Neelan Gill and her boyfriend – with whom Leo shares a close friendship.
Dinner date: The actor dined with dad George, step-mum Peggy and another rumoured love interest – American supermodel Gigi Hadid – London’s China Tang in July
In attendance: British model Neelam Gill, who is dating one of Leo’s friends, was also out in London on the same night
6. LONDON – JULY
The actor would pay more than one visit to London over the course of the summer, beginning with an appearance at musician Machine Gun Kelly’s private show in Mayfair.
He would soon return for a visit to the Dorchester Hotel’s China Tang restaurant, where he dined with dad George, step-mum Peggy and another rumoured love interest – American supermodel Gigi Hadid.
While Leo has also been linked to Betram, his connection to Hadid stretches back to September 2022, shortly after his separation from 25-year old girlfriend Camila Morrone.
A second date with Hadid and his parents would follow just 24-hours later, with the group booking a table at Chiltern Firehouse.
Here he is! In mid-July DiCaprio partied with Maya Jama and Neelam Gill at the Vogue Summer party (pictured)
Later that month he was back in town for an appearance at Marylebone venue Chiltern Firehouse, where he supported Love Island host Maya Jama – with whom he has been tenuously linked over recent weeks – at the Vogue Summer party.
Neelam Gill, an ever-present during Leo’s summer break by virtue of her relationship with one of his friends, was also in attendance as Jama celebrated her role as the face of Vogue magazine’s August edition.
As July drew to a close Leo kept a low-profile as he left Sir Mick Jagger’s 80th birthday party at Chelsea nightspot Embargo Republica.
The actor helped Sir Mick celebrate the milestone with guests including the singer’s daughter Georgia May Jagger, ex-wife Jerry Hall, and fiancée Melanie Hamrick.
Here he comes: Leo appeared to be auditioning for the vacant James Bond role as he arrived at popular Saint Tropez restaurant Club 22 via speedboat in July
There he is again: The actor was joined by close friend Tobey Maguire in the south of France
7. SAINT TROPEZ – JULY
By the end of the month it was business as usual for Leo, or at least it would be if said business involved cruising Mediterranean waters off the coast of southern France.
Leo appeared to be auditioning for the vacant James Bond role as he arrived at popular Saint Tropez restaurant Club 22 via speedboat.
Accompanied once more by Tobey Maguire, he later returned to his lavish yacht, where he was pictured frolicking on the top deck in a pair of blue beach shorts.
Party time: It wasn’t long before Leo and his entourage set sail for Sardinia, where the actor had good company in the form of a mystery brunette.
Seasoned traveler: Leo paid two visits to Sardinia and was surrounded by attractive women on both occasions
Loving life: One of Leo’s female friends was seen taking a dip in the Mediterranean
Familiar face: During his second trip to Sardinia he was in the more familiar company of British model Neelam Gill (pictured)
Side by side: But Gill was forced to deny any romantic attachment to the actor after their repeated joint appearances sparked inevitable rumours
8. SARDINIA – JULY
Indeed, it wasn’t long before Leo and his entourage set sail for Sardinia, where the actor had good company in the form of a mystery brunette.
Sporting a bottom-enhancing pink bikini, the unknown female appeared to overshadow Leo as they relaxed off the coast of the southern Italian island.
The actor was also joined by Swiss businessman Ernesto Bertarelli and the disgraced art dealer Hillel ‘Helly’ Nahmad.
Leo and Bertarelli were later seen boarding a plane at Olbia Private Airport – which has its own private jet terminal for wealthy travelers.
Evidently keen on Sardinia, he soon returned in the more familiar company of Neelam Gill – who was forced to publicly deny rumours of a romantic connection to Leo sparked by their repeated joint appearances.
Also along for the ride, a second mystery brunette would been seen holding the actor’s hand during his return trip to the picturesque island.
Pals: The actor was also joined by Swiss businessman Ernesto Bertarelli and the disgraced art dealer Hillel ‘Helly’ Nahmad (pictured) during his visit to Sardinia
Make way: in July Leo arrived in The Hamptons via helicopter, where he joined an attractive mystery woman on the runway
9. NEW YORK CITY/THE HAMPTONS – JULY
Leo returned to his home country for a flying visit that involved a brief stop in New York, where he was cruised around Manhattan island in a sporty looking Porsche convertible.
Day later he arrived in upmarket coastal enclave The Hamptons via helicopter, where ceaseless romance rumours were circulated once again after he joined an attractive mystery woman on the runway.
Leo’s mystery companion, whose connection to the actor is unknown, caught the eye in a black bralette, worn beneath a black leather bomber jacket.
But anyone thinking his holiday was over would be mistaken…
Surprise package: Former Love Island contestant Arabella chi has joined Leo in Ibiza
Loving life: Arabella (L) was joined by a female friend (R) as they relaxed aboard Leo’s yacht on the Balearic party island
Six degrees of separation: Chi’s connection to the actor comes via her current boyfriend, self-styled ‘king of nightclubs’ Richie Akiva – a close friend of Leo’s
My turn: Dutch catwalk model Imaan Hammam (L) was seen dining with Leo (R) at an Ibiza restaurant in August
Beach babe: The Oscar winning actor was joined by model Meghan Roche
10 IBIZA – AUGUST
With the European summer season entering its final month, Leo was back on the Med and in company more familiar with British TV viewers than fans of the Hollywood legend.
The actor has paid no less than two visits to Ibiza over the course of the summer, with his first finding him in the company of American model Megan Roche.
Upon his return, Leo revealed a hitherto unknown connection to reality TV personality Arabella Chi – best known for her past appearance on British dating show Love Island.
Chi’s connection to the actor comes via her current boyfriend, self-styled ‘king of nightclubs’ Richie Akiva – a close friend of Leo’s and a guest aboard his yacht during its stay off the coast of the Balearic party island.
More recently the actor has also been spotted with Dutch catwalk model Imaan Hammam at a local restaurant.
And with Sir Mick Jagger reuniting with Leo on the island as recently as Tuesday after welcoming him at his 80th birthday party, the holiday shows no sign of ending soon…
Don’t mind me: A mystery friend is seen relaxing aboard Leo’s yacht off the coast of Ibiza
Taking it easy: DiCaprio frolics aboard his yacht during its stay on the Balearic party island