Leonardo DiCaprio stole many hearts from the time he appeared on the big screen in Titanic, and since then, the Hollywood heavyweight has broken many hearts. The man who has been behind many great films and who is also a philanthropist and environmentalist, is not as devoted to his women as he is to his career. DiCaprio has a long line of girlfriends, none of which have become a wife to the 43-year-old. And what is the one thing all these women have in common? They are all models! Shocked? We beg to differ. But let’s face the facts, which woman would say no to dating Leo, especially when he is known for sweeping them off their feet and away on a luxe vacay. And as always, Leonardo DiCaprio is living the life, taking constant lavish and swanky vacations most of us cannot afford with his model girlfriends. And because DiCaprio has that marvellous reputation, the paparazzi love to follow him around and we always get a look at his blissful vacations and romances. It's not like Leo can maintain a low profile while he is globe-trotting with some of the most beautiful women in the world.
Stars like Leonardo DiCaprio are invested in the idea of relaxing and vacationing in some of the most beautiful locations around the world. When it comes to Leo, though, he definitely takes the cake in terms of luxury when treating his girlfriends to sunshine and sand — and sometimes, snow.
Click the button below to start this article in quick view
15 Aspen, Colorado
Leave it Leo to start the new year off with a new model girlfriend. Last month, DiCaprio was spotted with another drop-dead gorgeous woman by his side — the man just cannot settle for one model. Upon landing back in Los Angeles, DiCaprio was spotted with a young Argentinian model named Camila Morrone. The paparazzi are always ready for DiCaprio; the new rumoured couple were photographed getting off DiCaprio's private jet. DiCaprio took his new girlfriend to snowy Colorado for a ski vacation — how romantic. Because DiCaprio is no stranger to treating his loved ones to luxury, he made long-time pal and fellow actor, Tobey Maguire and his two children join the couple in Aspen. While DiCaprio tried to maintain a low-profile upon arrival in his grey hoodie and sunglasses, Morrone was just as flashy as his private jet.
14 Cabo San Lucas, Mexico
Before Camila Morrone, Leonardo DiCaprio was in a relationship with another young model named Nina Agdal, who we could have swore was finally the one to lock him down. In 2017, after rumours that there was cheating incidents, DiCaprio laid them to rest when taking Agdal to Mexico, so she can lay on the beach; and that is just one part of their globe-trotting romance. We are just unable to keep up with DiCaprio's romances and his tropical vacations — it is true that he has an affinity for both. The actor took his Sports Illustrated model girlfriend to hide out in Cabo San Lucas, and again, DiCaprio was not shy to invite his friends along. Although he seemed to want to hideout in the luxurious resort, who could not have spotted DiCaprio and his long-legged blonde ex-girlfriend.
13 Ibiza, Spain
When it comes to luxury, DiCaprio knows all about it, and on his time off, he does not shy away from going big and all in. Nina Agdal was a lucky woman to have hit up the poshest resorts, beaches, and islands in the world during her time with The Wolf of Wall Street actor. In July 2016, cheating and/or break-up rumours came to surface when DiCaprio was spotted on a yacht in Ibiza without his Danish model girlfriend as he was surrounded by gorgeous women. Later that same week, though, Agdal was spotted with him and his friends on the ultra-luxurious boat. While cruising the Mediterranean Sea, the couple was spotted loving life; sometimes cuddling up together with wine or taking dips in the water. DiCaprio also treated ex-girlfriend and friends to lunch at a very fancy restaurant on the Balearic Islands.
12 Tulum, Mexico
Is it even a surprise that DiCaprio has had so many ladies in his life? The blue-eyed actor knows just how to treat the ladies. It is also safe to conclude that DiCaprio does not like change when it comes to his preference in women and vacation destinations since he always dates models and often goes to the same countries. In October 2008, DiCaprio was dating Israeli model Bar Refaeli, which was also an on-and-off again relationship, but still, he always treats his woman to sunshine and luxury. DiCaprio met up with his ex-girlfriend Refaeli in Mexico to join her and her parents on a vacation in the country down South and spend quality time with her. Upon meeting up with her, he preceded to his luxurious manner and took the bombshell model to Tulum in Mexico to visit the historic ruins. And only DiCaprio and his model girlfriends could make exploring look so hot.
11 Ibiza, Spain
Is there somewhere we could apply to be a part of DiCaprio's entourage? His taste when it comes to vacationing and women is very lavish and high-end, and we want in. In October 2010, DiCaprio was still dating Bar Refaeli and we all thought she was going to be the one, but now let’s rewind to their romantic getaway together in the party city, Ibiza. The then-couple took a private jet as they jetted off to Ibiza to spend time together along with Naomi Campbell and Vladimir Doronin, who is a Russian billionaire. DiCaprio is one who indulges completely in the lifestyle of the rich and famous; during their trip, they relaxed and took part in some very fancy and exotic activities. The trip must have been just a little awkward, though; DiCaprio dated Campbell in the past.
10 Hawaii, United States
Sparks will fly, on the fourth of July — and they did, when Leonardo DiCaprio took his Victoria's Secret model girlfriend Erin Heatherton to Hawaii on the American holiday. The cameras were not shy as they followed around the two the entire time, especially when they hit a local beach in Hawaii where DiCaprio seemed to look "washed up." Though love was in the air for the two, the power couple are no longer involved romantically; of course, it is Leo we are talking about here. While the duo hung out at the beach in Hawaii for the American festivities, they were also joined by DiCaprio's best friend Tobey Maguire and other pals. DiCaprio spent a lot of time with his bikini-clad then-girlfriend alone on the beach, and we can confirm that it did not suck to be him.
9 St. Barts
Back to Nina Agdal, who we all thought would end up locking down DiCaprio. Not even a year ago, in May 2017, Agdal celebrated her 25th birthday in a way the rest of us could only dream of — all this thanks to the man himself. While DiCaprio's friend and actor Orlando Bloom was enjoying a sun-soaked vacation in the Caribbean, DiCaprio decided he join the British actor to celebrate his ex-girlfriend's 25th birthday in true rich style. The Danish beauty was accompanied by the two silver-screen actors on a yacht on her 25th birthday in St. Barts. Does it get any better than that? The birthday babe got to spend the entire evening with the two hunks who tried to maintain a low profile, along with other rich personalities on the vessel. Thanks to her famous friends, she rang in 25 with style.
8 French Polynesia
If Nina Agdal got to celebrate her birthday in lavish style, then so would the Oscar winner. Last year, for DiCaprio's 42nd birthday, he treated himself to a vacation in French Polynesia, along with his then-girlfriend Agdal, his mother, and friend Mike Medavoy, who was the producer of Shutter Island.
DiCaprio hit the jackpot by starting off his birthday by taking the group on his private plane, which landed on the island of Tetiaroa — at one of the few resorts that is accessible by plane. DiCaprio, the Entourage movie actress, and his friends all stayed at the fancy “Marlon Brando Resort” — just the name of the resort says it all — it is an "offer you can't refuse."
Before Leonardo DiCaprio and Nina Agdal started their hot romance, the two took a trip to the Bahamas together. This was when the relationship was apparently blooming into something serious, and what is more romantic than a holiday in the sun?
So far, this is the first trip on the list which does not include other people with DiCaprio and his leading lady. In June 2016, DiCaprio whisked off Agdal with him to the island for some alone time. Not only did he taker her to the Bahamas, but they stayed on the private island of Over Yonder Cay. This resort cost an estimated $75,000 a night, with a minimum stay of 7-nights on the island.
6 Bora Bora
During this sunshine getaway, DiCaprio put his lush brown locks in a man bun! It must be said because when he went on this vacation, there were photos circulating everywhere of DiCaprio and his man bun. Because DiCaprio knows best how to treat his leading ladies, he did not disappoint with his other then-girlfriend Toni Garrn. Back in April 2014, DiCaprio vacationed with Garrn in Bora Bora, where the two spent a lot of alone time together in the blue waters of the coast. Another Victoria's Secret model, DiCaprio was all over his gal while they took romantic walks along the shore.
5 Mykonos, Greece
Once upon a time, DiCaprio and Agdal were madly in love and making locals jealous in Mykonos, Greece. When the two took this trip together, not many photos were taken, and the public was trying to puzzle together who the woman Leo was with was. It was then revealed by a designer in Greece, that it was the foxy model that DiCaprio was dating — Agdal. DiCaprio took his private jet to the famous island where he, again tried, to maintain a low profile, but Leo cannot fool anyone. The model was seen strolling the streets with her very own "Jack Dawson," and she did not let him go.
The penchant that Leo has for the hottest women is also the same for vacation destinations — the two just go together. The man is a Hollywood actor and is also very involved in his own charity, raising millions of dollars, so it is no surprise that the man with expensive taste wants to relax aboard luxury yachts on the regular. And everything Leo does, he does in style. He arrived with model Kelly Rohrbach at the yacht in Saint-Tropez by small boat. Upon boarding the glamorous boat, he sported his trademark style with aviators and a polo and looked ready to enjoy the luxe vacay on the yacht.
3 French Alps, France
Sometimes, the man with the Victoria's Secret model catalogue likes to be a bit more adventurous, like when he decided to take a ski vacation. When DiCaprio was dating model Toni Garrn, he took her on a luxurious getaway for the holidays to the French Alps. During their winter getaway together, they bundled up at the Cap Horn ski resort in Courchevel, France. Joined by friends, once again, Leo also treated his company to lunch and drinks — the only pictures that were released to the public were of the two of them with friends on the patio. Sadly, this holiday vacation did not save DiCaprio and the German model's relationship.
2 Sardinia, Italy
One could date Leo for a month’s time, and he will sweep you off to a prestigious destinations. When dating Kelly Rohrbach, after only a month, he decided to bring his gal to one of the most romantic countries, Italy.
The paparazzi got many photographs of the star being very affectionate toward Rohrbach in Porto Cervo, Sardinia, Italy. The Hollywood stunner took the Sports Illustrated model to Italy and put her on a yacht, along with some friends. For once, it did not seem like Leo minded putting on a loving display for everyone to see; they were pictured nuzzling together, kissing, hugging, and even dancing on the yacht.
1 Miami, Florida
There is one question that Leonardo DiCaprio is always asked, and that is when and if he will ever get married. His answer is always along the lines of "when it will happen, it will happen," which to us, seems like a proper way to see that it will not. However, he has also mentioned that the only woman he will ever love is his mother, Irmelin. DiCaprio, in 2012, was vacationing with some friends when he decided to move his holiday to Miami so that he could have his mother with him to spoil her. Always keeping it low key, Leo was sporting a bucket hat to stay unnoticed while vacationing with his mother.
That was not the first time Leo brought his mom along on a posh vacation with him; he also had her join him like Gerard Butler and other friends in Italy, where they were all spotted enjoying a dinner together.
Leave A Comment
Looking for an AD FREE EXPERIENCE on TheRichest?Get Your Free Access Now!