It was a dream vacation for straight-A student Natalee Holloway and her senior classmates from Alabama’s Mountain Brook High School, who flew to Aruba in late May 2005 to celebrate their graduation on sun-drenched beaches and in pulse-thumping nightclubs.
But the dream soon became a nightmare for Holloway’s family, who learned of her disappearance on the morning she was to return home, as well as the residents of the Dutch Caribbean hotspot, who saw their island become a lightning rod for media criticism amid fruitless efforts to find the missing teenager.
And while the primary suspect, Joran van der Sloot, eventually ended up behind bars, it only came after he killed another young woman, a sad coda that provided only partial closure to the still-unsolved Holloway case and sparked more questions as to how her investigation could have been handled differently.
May 26, 2005: Holloway and her classmates arrive in Aruba
The group, consisting of 124 students and seven adult chaperones, settles in at the Holiday Inn Resort near the northern end of the island.
May 29, 2005: Holloway meets van der Sloot at the hotel casino
The 17-year-old Dutch national, who lives nearby in the town of Noord, chats up Holloway and her friends as they enjoy their final evening on vacation. Van der Sloot later joins the American contingent at the popular Carlos ‘n Charlie’s bar in downtown Oranjestad, where he drinks and dances with Holloway.
Sometime after the bar closes at 1 a.m., Holloway is seen leaving in a car with van der Sloot and his two friends, Deepak and Satish Kalpoe.
May 30, 2005: Holloway is a no-show for the class departure
After friends are unable to locate Holloway in their hotel – her passport and bags remain untouched in her room – a chaperone relays the news to Holloway’s mother, Beth Holloway Twitty.
That night, Twitty, her husband Jug (Holloway’s step-father) and family friends arrive in Aruba on a rented jet. Their questioning takes them from the Holiday Inn to Carlos ‘n Charlie’s and eventually to the van der Sloot home in Noord.
Van der Sloot admits he left the bar with Holloway and the Kalpoe brothers and drove to a lighthouse, before dropping her off at the Holiday Inn. He leads the group to the hotel, promising to point out the security guard who allegedly helped her inside, but is unable to find the guard.
June 1, 2005: The first local search team is organized
With Holloway not officially determined to be “missing” yet, a group of approximately 100 tourists and various locals starts combing the area. In the coming weeks, the search expands to include a volunteer team from Texas, Aruban police, Dutch Marines and three F-16 fighter planes from the Netherlands, though none are able to locate any sign of Holloway.
June 5, 2005: Police make their first arrests
The first suspects detained in the case are former security guards of a hotel closed for renovation, though they are released eight days later. Authorities would also soon arrest and release van der Sloot’s father Paulus and a party-boat DJ.
June 9, 2005: Van der Sloot and the Kalpoe brothers are taken into custody
Under pressure from the Twittys and government officials, deputy police chief Gerold Dompig arrests the three young men who were last spotted with Holloway. The suspects now change their story, with the Kalpoe brothers claiming they had dropped their friend and Holloway off at a beach near the Holiday Inn, and van der Sloot insisting he had left her there to walk home.
July 4, 2005: A judge orders the release of the Kalpoes
It is also announced that van der Sloot will be held for another 60 days. No reason is given for the judge’s decision.
July 17, 2005: Hair strands raise hopes for a breakthrough
The strands are found stuck to a piece of duct tape on Aruba’s northeast coast and sent to the FBI crime lab in Quantico, Virginia, which returns the news of a negative match to Holloway on July 28.
July 26, 2005: Investigators begin draining a pond
Acting on a tip from a gardener, who claimed to have seen van der Sloot and the Kalpoes digging next to the nearby Mariott Hotel, authorities start draining the pond across from the Mariott. They abandon the effort on July 30.
September 3, 2005: Van der Sloot and his friends are set free
One week after the Kalpoes are re-arrested, the brothers and van der Sloot are released from prison on the condition that they remain available to the police. “The investigation continues,” the lead officer tells The Associated Press. “The case of Natalee Holloway has not concluded with these releases.”
February 16, 2006: Van der Sloot and his father are served civil lawsuits in New York City
The suit, filed with the Supreme Court of the State of New York, accuses Joran of “malicious, wanton and willful disregard of the rights, safety and well-being” of Holloway and claims Paulus enabled his son’s predatory behavior. The suit is later dismissed on August 3, with a judge determining that local taxpayers would only have an “ephemeral” interest in seeing the case through.
March 1-3, 2006: Van der Sloot gives his side of the story to Fox News
In a lengthy interview with Greta Van Susteren that airs over the course of three nights, van der Sloot recounts the details of his time with Holloway, from drinking with her at the bar to leaving her behind on the beach, addressing some of the unusual elements of his story such as why his shoes went missing that night.
December 14, 2006: Holloway’s parents take legal action against the Kalpoe brothers
Twitty and Holloway’s father, Dave Holloway, take aim at the other two primary suspects and file a wrongful death suit against the Kalpoe brothers in Los Angeles Superior Court. However, location once again proves the undoing, as a judge dismisses the suit over a lack of jurisdiction on June 1, 2007.
November 21, 2007: Van der Sloot and the Kalpoe brothers are arrested again
Van der Sloot is apprehended in the Netherlands, where he attends school, while the Kalpoes are held in Aruba after the emergence of what is described as “new incriminating evidence.” However, the evidence fails to move the case forward, and all three suspects are released by December 7.
December 30, 2007: Divers investigate a fish trap off the Aruba coast
The efforts of an American search vessel and a remote-operated vehicle yield pictures of what appears to be a human skull, though this development becomes the latest dead end when divers find nothing relevant in the trap.
February 3, 2008: Van der Sloot says Holloway’s body was dumped at sea
In a broadcast of hidden-camera footage set up by Dutch reporter Peter R. de Vries, van der Sloot tells an associate that Holloway had collapsed when they were on the beach together and, unable to revive her, had a friend help dispose of her body from a boat. Made aware that his alleged confession was recorded, van der Sloot insists he was lying at the time.
March 29, 2010: Van der Sloot seeks a financial arrangement
In an email to Twitty’s lawyer John Q. Kelly, van der Sloot offers to reveal the location of Holloway’s body in exchange for $25,000 upfront and another $225,000 to come. Kelly agrees and relays the information to the FBI.
May 10, 2010: The lawyer meets with van der Sloot
After Kelly takes $10,000 to a meeting with van der Sloot in Aruba, the latter leads the way to a house and says his father buried Holloway in its foundation. That day, another $15,000 is wired to his bank account in the Netherlands. Van der Sloot later admits to Kelly that he had been lying again, and covertly travels to Peru to take part in a poker tournament.
May 30, 2010: Van der Sloot kills a young woman in Peru
Five years after the disappearance of Holloway, van der Sloot kills 21-year-old Stephany Flores Ramirez in his hotel room in Lima, Peru. Her body is not immediately discovered, however, as her killer had left instructions that forbade hotel staff from entering his room.
June 3, 2010: Van der Sloot is arrested in Chile
Sporting a short, dyed-red hairdo, van der Sloot is found in a taxi near the coastal city of Vina Del Mar, Chile. He is taken back to Lima and held in the high-security Castro Castro prison.
June 27, 2010: Van der Sloot is indicted in the U.S. for wire fraud and extortion
The indictment stems from the federal investigation that followed van der Sloot’s attempt to acquire $250,000 from Holloway’s mother. When asked why the suspect wasn’t arrested after the wire payment – and before he had the chance to kill Flores – authorities said there wasn’t “sufficient evidence” to do so.
January 11, 2012: Van der Sloot pleads guilty to the murder of Flores
“I wanted from the first moment to confess sincerely,” van der Sloot says in court. “I truly am sorry for this act. I feel very bad.” The defense blames his actions on the “extreme psychological trauma” suffered from the long-running Holloway saga, though prosecutors contend he killed Flores to rob her of her winnings from a casino.
January 12, 2012: Holloway is officially declared dead
At the behest of Holloway’s father, and against the wishes of her mother, Holloway is formally declared dead by an Alabama judge. “Beth’s position is she has no proof or indication that Holloway is still alive, but absent any proof or indication that she is dead, she always wants to hang onto that slight glimmer of hope,” her lawyer says.
January 13, 2012: Van der Sloot is sentenced to 28 years in prison
Two days after his guilty plea, van der Sloot is sentenced to 28 years behind bars and ordered to pay $75,000 in reparations to the victim’s family. While Holloway’s family remains hopeful that van der Sloot will face additional punishment in the U.S. for the extortion charges, they later learn that the convicted murderer won’t be extradited for another quarter-century.