Leonardo DiCaprio, 49, drinks red wine with girlfriend Vittoria Ceretti, 26, in Portofino, joined by Tobey Maguire and Emily Skinner

On Monday night, the gorgeous Vittoria Ceretti, the girlfriend of actor Leonardo DiCaprio, 49, was spotted enjoying a holiday in the charming town of Portofino, Italy.

Before dining al fresco at the popular La Gritta Restaurant in the area, the two appeared relaxed as they enjoyed the Italian coastline.

The Dolce & Gabbana model was once spotted smoking a cigarette while out on a date with the handsome actor.

Tobey Maguire, 49, and Lukas Haas, 48, who were Leonardo’s childhood friends, were also spies during the summer break.

Leonardo DiCapri , 49, was seen with his stunning model girlfriend Vittoria Ceretti, 26, when on vacation in picturesque Portofino, Italy on Monday evening

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The brunette beauty - who is known for her runway work in Europe - was never far from the Once Upon A Time... In Hollywood actor's side

Among them was Edward Kobina Enninful, 52, a British stylist and editor of Ghanaian descent who served as Condé Nast’s European editorial director and chief editor of British Vogue. Alec Maxwell, his partner, was accompanying him.

Southeast of Genoa is the fishing hamlet of Portofino on the Italian Riviera. From the Piazzetta, a path leads to Castello Brown, a museum and stronghold from the 16th century featuring panoramic views of the town and the Ligurian Sea as well as art exhibitions.

Vittoria kept her dark hair down and wore a black hoodie over a dazzling gunmetal gray minidress. She added earrings and a necklace set in diamonds.

The cover model accessorized with black flat sandals with strappy heels that would have fit perfectly in the Gladiator movie.

Leonardo, sporting a LA Dodgers cap over his longer-than-normal blonde hair, was dressed in all black, maintaining his typical casual look.

In addition, the Titanic star was spotted chatting up his male pals while enjoying a glass of red wine. Additionally, there was Tuscany-sourced Italian Panna water on the table.

Tobey, seated among a group of males, was dressed simply in black and sipping wine.

Emily Skinner, an actress most known for her work on Disney Channel’s Andi Mack and the Brat network, was also in attendance!

The movie idol sipped red wine next to a male friend - also in black - who did the same

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DiCaprio had a slight beard as he enjoyed his meal with his mask off but his cap down low over his eyes

The 21-year-old rising sensation was also a cast member of Total Eclipse and Crown Lake.

Her blonde hair was down, and she wore a strapless dress with a flowery motif and a beautiful gold necklace.

The actress was spotted sitting close to Haas, who was wearing a T-shirt and had a gold band on his pinkie finger. Haas appeared interested in the conversation.

The scene was elegant.

Lorenzo Raggio established La Gritta in 1954. was the gathering place for the international jet set and royalty that docked in Portofino throughout the 1960s and 1970s. La Gritta offers inventive meals that focuses mostly on fish. According to the website, “Exclusive wines and champagnes enhance the dining experience.”

Vittoria is a fashion model from Italy, age 26. In 2012, Ceretti was found via the Elite Model Look Model competition.

Ceretti has taken part in 400 fashion shows as of 2024, and she has made 23 appearances on the cover of Vogue and its international editions.

She approached a male model earlier this month while they were filming a Dolce & Gabanna commercial.

After fervently promoting his most recent film, Killer Of The Flowers Moon, from last fall until this year’s Oscars, DiCaprio must be relishing his break.

Also spied on the summer vacation was Leonardo's childhood pals Tobey Maguire , 49, far left. On the right is Edward Kobina Enninful, 52, a Ghanaian-born British editor and stylist who was editor-in-chief of British Vogue and European editorial director of Condé Nast, was also in the mix. He was with his partner Alec Maxwell, center with the white shirt on

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The former child TV star seemed to hold court as he entertained his many friends

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Leonardo seemed to be at the head of the table as two men looked at him

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Also seen was Emily Skinner, the actress known for her roles on Brat network and Disney Channel's Andi Mack! The 21-year-old budding star was also on the TV series Crown Lake and Total Eclipse. She was seen sitting near Haas as he looked intrigued in the conversation.

The star’s next project could be to portray legendary singer and actor Frank Sinatra.

A Sinatra biopic is slated to be directed by Martin Scorsese.

The 81-year-old director is working on a film that will feature the My Way crooner, who he frequently collaborates with.

Jennifer Lawrence, a friend of Leo’s, might portray Ava Gardner, the Golden Age pinup actress who was the singer’s second wife.

Variety claims that because the star’s daughter Tina Sinatra manages his estate and has not yet given her approval for the film, Scorsese’s Sinatra biopic may run into trouble.

Gardner was the one who ended Sinatra’s union with Nancy Barbato, Tina’s mother.

Apple, which provided funding for Scorsese’s previous film Killers of the Flower Moon, is keen to collaborate with the director once more, although Sony is reportedly in the lead to acquire the project’s rights.

If the Sinatra biopic is successful, it will be Scorsese and DiCaprio’s ninth collaboration, and the director has praised “The Revenant” star as a “natural film actor.”

“What’s great about Leo, and the reason we work together so often, is that he goes there,” the director of Taxi Driver stated.

He travels to these strange, complex, and challenging areas, and someway, through the confusion, we can arrive at a clarity.

And most of the time, it’s in his eyes, face, and expression. I told him this all the time. He’s a born actor in movies. It wouldn’t matter if I shot a close-up of him thinking nothing at all and then intercut anything with it—people would just assume, “Oh, he’s reacting to such and such.”

“His eyes catch the attention of the camera because of something in his face.”

Her legs were bare and tanned as she walked past other outdoor diners who did not notice Leo

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Leo had a gray mask over his mouth but not his nose so fans would not recognize him

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The star often vacations on yachts in the Mediterranean during his summer down time

Timothée Chalamet disclosed the advise DiCaprio provided him earlier this year.

The 28-year-old actor has shared the wise counsel that his co-star Leonardo from Don’t Look Up gave him, which included declining an offer to be in a DC or Marvel film.

According to what he told The New York Times, Leonardo DiCaprio advised him, “No superhero movies, no hard drugs.” This, in my opinion, was excellent. I adhere to both of them!

It turns out that the 2008 DC Batman film The Dark Knight, directed by Christopher Nolan, was the reason he initially decided to pursue acting.

But he went on, “The Dark Knight is a superhero movie that inspired me to act.” I would have to give it some thought if the director and screenplay were excellent.

When the star of Dune: Part Two went in for an audition to play the lead in Spider-Man: Homecoming, he almost got a superhero role.

During the 2017 film’s audition process, Chalamet read twice for the role of Peter Parker and his crime-fighting alter ego, which ultimately went to Tom Holland. Chalamet claimed his agency had to stop him from showing up at the Marvel headquarters to try out a third time.