Once upon a time it was only sailors who had a girl in every port, but in Leonardo DiCaprio’s case this is not the case, especially if it concerns his summer vacation. The actor spends a lot of time on his boat in the ocean, while visiting some of Europe’s hottest holiday destinations. And he also had an attractive company, in his every “sea”… step. From Russian catwalk goddesses to UK fashionistas and an unlikely relationship with a former contestant from a well-known reality show.

CANNES – MAY

Ironically, it all started on land when Leo made an appearance at the 76th annual Cannes Film Festival. Accompanied by co-stars including renowned director Martin Scorsese, the actor was there to celebrate the launch of their upcoming film, the highly anticipated ‘Killers Of The Flower Moon’. What started as a professional obligation soon turned into a vacation, as the famous actor “traded” the red carpet for the lower deck of billionaire James Packer’s yacht. Accompanied by close friend Tobey Maguire, the actor hung out with Irina Shayk, the rumored girlfriend of former NFL star Tom Brady. He even found time to make a special appearance at his girlfriend Naomi Campbell’s birthday in the French resort.

But for Leo, the party had just begun…

AMALFI COAST – JUNE

Within days the actor had flown to Italy’s Amalfi Coast, where he met up with his family for dinner in Naples. However, he would soon return to his yacht, moored off the Italian coast, to sunbathe with his 15-year-old niece Normandie. During repeated visits to southern Italy, the actor was captured relaxing on the coast of Sorrento, a short distance from the picturesque fishing village of Nerano.

FLORENCE – JUNE

A thirst for culture and history led Leo to return to land, if only for a fleeting trip to the city of Florence in central Italy. The actor visited a historic chapel with his family before reuniting with old friend Tobey Maguire, Maguire’s ex-wife Jennifer Meyer and the former couple’s children. Later that evening he and Maguire went for a walk in the Piazza della Signoria.

FORTE DEI MARMI – JUNE

Next stop is Tuscany and a family dinner at the popular seaside restaurant Maitó, in the Italian seaside town of Forte Dei Marmi. Famous for its seafood and wood-fired pizza, the restaurant welcomed the actor and his entourage.

PARIS – JUNE

With fashion week underway in the French capital, Leo used the event as an opportunity to reunite with model Rose Bertram. The actor has been romantically linked with the particular model and their joint appearance at the restaurant “L’Avenue” has reignited the rumors of a new romance of the Hollywood star. During the same trip she was seen leaving the Hôtel Costes, before tucking into an evening meal at ‘Loulou’ with model Neelan Gill and her boyfriend, with whom Leo is close friends.

LONDON – JULY

The actor will make more than one visit to London over the summer, starting with an appearance at 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 his family and Gigi Hadid. A second date with Hadid and his parents would follow just 24 hours later, with the group booking a table at the Chiltern Firehouse.

Later that month she was back in town for a show in Marylebone at the Chiltern Firehouse, where she supported ‘Love Island’ host Maya Jama, with whom it seems she’s been ‘running’ for the past few weeks… Neelam Gill is, too , present at Leonardo DiCaprio’s summer vacation. And as July drew to a close, Leo kept a low profile as he left Sir Mick Jagger’s 80th birthday party at Embargo Republica nightclub.

SAINT TROPEZ – JULY

Leo looked like he was auditioning for the role of James Bond as he arrived at popular Saint Tropez restaurant ‘Club 22’ by speedboat. Escorted once again by Tobey Maguire, he later returned to his luxury yacht, where he was snapped having fun on the top deck, wearing a pair of blue shorts.

SARDINIA – JULY

Indeed, the actor and his entourage soon set sail for Sardinia, where the actor had good company in the form of a mysterious brunette. Wearing a pink bikini that showed off her figure, the unidentified woman was seen shadowing Leo as they relaxed on the shores of the southern Italian island.

The actor was also joined by Swiss businessman Ernesto Bertarelli and art dealer Hillel ‘Helly’ Nahmad. Leo and Bertarelli were later seen boarding a plane at Olbia’s private airport, which has its own private jet terminal for wealthy travelers. Apparently smitten with Sardinia, he soon got back together with Neelam Gill, who was forced to publicly deny rumors of a romance with Leo, sparked by their appearances together.

IBIZA – AUGUST

Leo returned to the Mediterranean and with company more familiar to British TV viewers than fans of the Hollywood legend. The actor visited Ibiza twice over the summer, with the first finding him in the company of celebrity model Megan Roche.

On his return, Leo revealed a previously unknown relationship with Arabella Chi, known from her appearance on a British reality show. Chi’s connection to the actor comes through her current boyfriend, self-proclaimed ‘nightclub king’ Richie Akiva, a close friend of the actor and a guest on his yacht during his sojourn off the coast of the Balearic island for parties. Most recently, the actor was spotted with model Imaan Hammam at a local restaurant.