It was shortly after 11 a.m. on Friday when the twin engine Britten Norman BN2 Islander prop plane carrying Italian fashion mogul Vittorio Missoni and three other passengers took off from the Los Roques islands, 95 miles from Venezuela, and then disappeared minutes later over the blue Caribbean.

Within minutes after the plane dropped off the air traffic control radar, rescue crews started scouring the land, air, and sea around the Los Roques archipelago. The Italian press reported Saturday that a dedicated search ship equipped with high-powered sonar had joined the rescue mission. Despite their efforts, by late Saturday, after intensive searching, no traces of the missing vacationers or their aircraft had turned up.

Scion of designer Ottavio Missoni and chief administrator of the iconic Milan luxury fashion house Missoni, the 58-year-old executive was wrapping up tropical Christmas and New Year holidays with his wife, Maurizia Castigligioni, and two Italian friends, at the tony tourist resort island, a crescent of 50 islands just a short hop from the Venezuelan mainland. Missoni was booked to fly later that night to Madrid and then on to Italy, where Missoni executives are preparing to unveil the brand’s latest designs at a fashion extravaganza in Milan later this month.

The company was founded in 1953 by Ottavio and Rosita Missoni. Their three children, Vittorio, Luca, and Angela (its current designer) took over the brand in the 1990s and currently co-own it. They are seen as turning the business around, and it now produces sales estimated between $75 million and $100 million annually. Vittorio, known as the Missoni “ambassador,” has recently been in charge of the brand’s international expansion.

Also missing in the apparent crash were two crew members of the Albatros Airlines airliner, including the Venezuelan-born pilot, Germán Marchan, 72. According to the Venezuelan newspaper, El Universal, Marchan spoke to the flight tower from the cockpit for the last time at 11:30 a.m., some 10 miles south of Los Roques airport.

Famed as a lover’s retreat, Los Roques also has earned something of a reputation for air traffic accidents. In a hauntingly similar episode, a plane that took off from Los Roques in January 2008 also disappeared over the Caribbean without a trace. Of the 14 people aboard, only the pilot’s body washed ashore. No traces of the remaining passengers or debris from the downed plane were ever recovered.

A year later, another small aircraft flying from the islands to the mainland also crashed into the sea, though all nine people aboard were rescued.