1. Cruising the Aegean Sea

Year Purchased: 2021
Estimated Value: $70 million* (Price of Eos yacht) 

Before Jeff Bezos went to space in 2021, he went on a cruise. He was spotted visiting the Greek Islands aboard a super-luxurious yacht. He went on a cruise of the beautiful Aegean Sea, and he was spotted having dinner at Omega3, a cosmopolitan restaurant in Platis Gialos, located on Sifnos, a Cycladic Island.

Bezos wasn’t alone for this cruise. He went sailing with his fellow billionaire businessman, Barry Diller. Diller’s wife is famed fashion designer Diane von Furstenberg. Also along for the trip was Anderson Cooper, a journalist and anchor at CNN. The trio sailed on Eos, one of the world’s largest sailing yachts. Eos is owned by Diller.