Despite gloomy gray skies, the 137-boat Baja Ha-Ha XVIII rally fleet headed south with boundless enthusiasm. It was no wonder the mood was upbeat, though, because for many of the 503 participants this 750-mile cruise to Cabo San Lucas serves as the inaugural step into a new life of cruising.

As in years past, the two-week event began on a festive note yesterday, with a Costume Kick-Off Party at West Marine’s Shelter Island compound. In attendance were all sorts of gnarly pirates and saucy wenches, as well as a broad range of other colorful characters, who might have given passersby the impression that they’d stumbled onto the back lot of a movie studio. Needless to say, it was all great fun, with West Marine managers Galen Piltz and Louis Holmes emceeing in elaborate swashbuckling attire.   

On the way out to the 11 a.m. start, the fleet gave a unified salute to the Port of San Diego, which has been a generous host to them for 18 years, in the form of a boat parade past downtown, then Harbor and Shelter Islands. With TV, radio and print journalists recording the departure, local dignitaries and well-wishers waved the fleet onward toward the sunny skies of Baja.

The longest of three legs began today, a 360-mile blast to the fishing village of Bahia Tortugas (Turtle Bay). We’ll attempt to send another report from there, with additional reports from the event’s final destination, Cabo San Lucas. In the meantime, you can follow our Spot position reports on our Facebook page and our near-real time track here. With any luck it will be "lovely cruise" — to borrow a line from Jimmie Buffet.

With this morning’s start of Baja Ha-Ha XVIII — the ‘Barely Legal’ Ha-Ha — Saturday and Sunday were the Costco runs for much of the Ha-Ha fleet. With 12 to 14 crew on the mothership Profligate each year, the Costco run has become a hallowed tradition.

Why we go to the Moreno Avenue Costco is something of a mystery, as it’s surely one of the most crowded Costcos in the world. It starts with a battle to get into the parking lot, followed by a mini-marathon walk to the store entrance, followed by near-open warfare in the aisles. Total chaos.

Prior to starting to shop, Profligate‘s provisioning is organized to minute detail. Lists are made and each member of the shopping crew is assigned specific tasks. Once inside the store, however, all hell breaks loose, and members of the team basically load the carts with whatever and however much of it strikes their fancy. There’s an attractive childlike quality to it.

We always meet at least one other member of the Ha-Ha fleet while shopping at Costco. This year it was Mark Sciarretta of the Zig Zag, Oregon-based Lagoon 380 Younger Girl. As he got whacked in the back of the head with a sack of canteloupes by a careless woman, we moaned that he’d "forgotten how to provision."

Even though Costco sees a lot of big shoppers, the Profligate cart train to the checkout area attracts a bit of attention. Even the Costco honchos were impressed, setting aside two cash registers just for us. The guesses on the total ranged from $2,200 to $3,000. Thanks in a large part to the fact that we also did provisioning for later in the season, the tab came to nearly $3,000. There will be no starving on Profligate this year. And if the reports of massive numbers of yellowfin, bluefin and mahi 160 miles to the south of San Diego are true, we might not even need half the meat that was purchased.

Doña de Mallorca’s speciality is wine. She seems to have struck up a chummy relationship with the guy in charge of the wine department, who has no trouble remembering her from year to year. But due to the general chaos, the wine cart was somehow misplaced near frozen foods and — oh no! — never made it to the checkout. Fortunately, it was Saturday, so there was yet another day of shopping left.

If anybody missed anything during their Costco runs, there is no need to worry, as there are Costcos in Cabo and Puerto Vallarta, too.