"The race is won at night," said Dave Lee, who has been sailing the race since the late 1960s.
He joined the crew of Amante, a 48-foot sloop based on Lido Isle. Amante's crew hoisted three small yellow flags from its starboard side, each one indicating 10 years of racing this event.
The historically light-hearted event brings out many who swill beers during the day, but some are serious sailors, with crews in matching shirts and hats.
"We're competitive, but we're not cutthroat competitive," said Amante's skipper Tim Richley, who grew up sailing in Newport Harbor. His father, Mel, designed the boat and his mother, Rickie, prepares food for the crew each year.
"It has always been a family thing," he said.
At the start off Balboa Pier, about 175 boats gathered, a number that's gone down from years past. The number of race entrants has slid as the tepid economy and fears of drug violence in Mexico dampened enthusiasm for some sailors.
Also, a race to San Diego called the Border Run began to siphon off racers in 2009 and surpassed the number of entries the Ensenada race had this year.
At the Ensenada race's popularity peak in 1983, 675 boats raced south. Last year, there were 217 boats. Meanwhile, the Border Run jumped from 111 in 2009 to 233 last weekend.
The lower number of racers didn't hurt the annual send-off party at the Bahia Corinthian Yacht Club on Thursday, said the club's catering manager Danielle Harden. It saw more attendees this year than last, and police shut the gathering down at 11 p.m.
Sailors' families, some of whom drive to Ensenada together, will pick up the party at the Bahia Hotel in Ensenada.