On 2 February, 1953, aged 18, he embarked on a ship from the port of Piraeus, for a 6-month unpaid work placement, having to cover his own food expenses. In the 20 years of his career at sea he worked his way up to master. In 1962 he met Carmen Kyritsis, whom he married in 1964; they had three sons together.

In 1974, Captain Vassilis founded Costamare Shipping Co S.A. and he soon acquired the first vessel of his fleet, a small cargo boat which he renamed CARMEN. The early 1980s was a difficult time for the marine sector, which was facing a crisis. He, however, with the firm belief that “there is no easy and no difficult thing, there is only what you know and what you don’t know,” decided in 1985 to turn his attention to container ships. This move in the following years led to the creation of the largest independent private cargo shipping company in the world.

In the mid-1980s, the grand vision of Costa Navarino was born; it was to be a quality investment that on the one hand would give Messinia a prominent place on the global tourist map, and on the other hand would allow the people of the area to remain in their homeland. In 1997, having already acquired a great portion of the land required, Captain Vassilis founded TEMES, which assumed the realization of the project.

In May 2010, the first area of Costa Navarino opened to the public, which includes hotels, a golf course, a conference center, a spa, and many more facilities, expanding over approximately 321 acres of land. In October 2011, the second golf course came into operation, in the area that has been developing near Pylos.

In 1999, Captain Vassilis founded GEOHELLAS, a mining company specializing in extracting, processing, and distributing inorganic fossils from the company’s mines in Macedonia.

Captain Vassilis had been a passionate environmental activist since the 1970s. He was one of the first members of the Hellenic Marine Environment Protection Association (HELMEPA), and a founding member of HELMEPA Junior, whose exhibition is housed in the building of Costamare. In 1998, HELMEPA Junior received UNEP’s (United Nations Environment Programme) Global 500 award. In 2008, Costamare was the first shipping company in the world to fully comply with the new international CO2 regulations.

Captain Vassilis always believed that “taking fills your hands, but giving fills your heart.” Alongside his environmental activism, he also became involved in various causes such as seamanship, Hellenism, Orthodoxy, and education. He was a member of the Board of Directors of Greek and international organizations, and was many times recognized and awarded for his activities and contribution, by significant entities such as the Academy of Athens, the Ecumenical Patriarchate of Constantinople, the seven Chambers of the Peloponnese, the Hellenic Chamber of Hotels, the Entrepreneurs’ Club, and many others.

In 2005, after 57 years of service, Captain Vassilis announced that he would be retiring in order to devote more time to his wife, Carmen, and his then-newborn grandchildren, leaving the management and administration of the companies to his three sons. On 25 January, 2011, he embarked on his final journey, having had many grandchildren and having fulfilled many of his plans and dreams, on both land and sea.