Estimated price: More than $500 million
Amazon founder Jeff Bezos is one of the richest people in the world, so it makes sense he'd want one of the most expensive yachts in the world. Commissioned in 2018, the reportedly $500 million-plus vessel called Y271 was built in the Netherlands by Dutch company Oceanco. It is a whopping 417 feet long, according to Architectural Digest, making it the world's biggest sailing yacht. In true mega-billionaire fashion, Bezos asked the Dutch city of Rotterdam to dismantle a section of its historic Koningshavenbrug Bridge in order for the yacht to pass through, but the answer was a resounding no after an outcry. The drama continued as Bezos recently had the vessel towed away in the dead of the night to a further shipping yard, presumably when angry Dutch residents wouldn't be out to throw eggs at the monstrosity. Amazingly, this monster of the seas won't accommodate a helipad, so Bezos has commissioned a backup yacht to allow his girlfriend, Lauren Sanchez, a helicopter pilot, a place to land her bird. Fun fact: The cost of the yacht is about twice what Bezos paid to buy The Washington Post in 2013. Alas, pictures of the secretive project are hard to come by so far.
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