
Smooth Sailing South on the 31st Baja Ha-Ha
Latitude’s Nicki Bennett sends this report from the 31st Baja Ha-Ha.
The 31st Baja Ha-Ha fleet is making its way south under near-ideal conditions. The weather has been kind, the water turning warmer and more turquoise by the day, and today brought the first clear sunny morning as Profligate and the rest of the fleet continue down the Baja coast.

Sunday’s sail was one to remember. Dolphins escorted us out of Turtle Bay, reappeared midday, and then returned in full force at sunset, chasing our wake through the golden light. Yesterday, whales were spotted up and down the coast, and other boats reported sightings of orcas as well. The active sea life has made for some decent fishing along the way. Boats have been reporting catches of dorado, wahoo and tuna as we sail south. Aboard Profligate we landed one tuna that made for excellent sashimi, along with a few bonito that we released after leaving Turtle Bay. This morning we successfully caught three dorado and are planning a fish taco feast for dinner.
While a few crews have faced their share of technical challenges, most issues have been manageable. There have been some autopilot, electrical, and battery problems, largely solved along the way. Two boats are dealing with windlass issues, including Profligate, though both have found ways to work around them. Ullman Sails’ Chuck Skewes had to make only one sail repair in Turtle Bay, and a few minor rigging issues were resolved before departure. One banjo bolt on a Volvo Penta engine sheared off before Turtle Bay, but the resourceful crew managed a solid jury rig and continued south. Two spare batteries were loaned out to help fellow sailors, and one boat, Finest Kind, turned back to San Diego to make repairs before heading south again. All told, there have been no major mechanical or medical issues to report.
The fleet enjoyed an extra lay day in Turtle Bay due to a wind forecast, which gave everyone time to rest and explore. Several cruisers hiked up the ridge overlooking the bay for a spectacular view of the anchored fleet. The extra time also allowed many to wander through the remote village, visit the historic church built in 1887, and walk to the cemetery that overlooks the bay, a quiet spot rich with local history.


This Ha-Ha marks several lasts for the Grand Poobah, including his final ceremonial pitches at the always-popular Bazeball game, which saw great attendance once again. The annual tradition continues to be a highlight of the stop in Turtle Bay, with loads of donated equipment distributed to local kids after the game.

A few new activities were added this year, including yoga sessions, one on the beach and another on the baseball diamond. Turtle Bay is also building a soccer stadium, which hints that next year’s Ha-Ha might include a soccer match on the schedule.
Volleyball was as lively as ever, with two nets in play, one set up for Thursday’s matches and another for the energetic games during Saturday’s beach party. That beach party was a big hit, drawing a huge crowd and raising nearly $800 for charity through hot dog sales. The women continued their winning streak in the always-popular tug of war, once again proving unbeatable on the sand.

This year’s fleet has been a wonderful mix of Ha-Ha veterans and younger cruisers heading out on their first bluewater adventure, many thanks to the connectivity Starlink provides. Though there is less unplugging from back home along the way, that connection has been a great tool for solving and troubleshooting technical problems underway. The fastest boats in the fleet are nearing the second stop in Bahia Santa Maria, and as of this writing, Profligate is expected to arrive not too long after dark.
Caption Contest(!)
Welcome to November’s Caption Contest(!). Here’s something that might be useful on the Bay when the winds just won’t blow.

See October’s winners in the November issue of Latitude 38.
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Coyote Point YC Ends Saturday Series With Commodore’s Cup
The Coyote Point Yacht Club’s (CPYC) Saturday racing series drew to its grand finale with the Commodore’s Cup, and the Bay delivered a day worthy of its name. Clear skies, sun glittering on the chop, and a gentle forecast that promised light winds over roughly eight-and-a-half miles. The course began with a rabbit start at the marina to C, then to Z, then SF1, A and 8, and then home.

Seven boats flew the CPYC colors: Lorelei, Paradigm, Sirius, Surprise!, Svea, Sweet Grapes, and Ventus. Four commodores graced the waters: current commodore Stephen Swanson and past commodore Mark Green aboard Sweet Grapes; past commodore Mark Neumann helming Lorelei; and past commodore Yvette Yong on Paradigm. A fine turnout of leadership, salt and tradition.
Ventus took on rabbit duties. Svea crossed first, with Sweet Grapes snapping at her stern. Paradigm and Sirius set their sights eastward on the run to Mark C. Sweet Grapes tacked early, while Ventus stood on, biding her time for a later tack, and it paid handsomely. Ventus, then Sweet Grapes, rounded C, with Paradigm in third.
Positions held at Z. Ventus and Paradigm wasted no time tacking west toward SF1. Sweet Grapes hunted for advantage in the channel, hoping the ebb might give her a lift, but the sea was not in the mood for charity. She tacked and joined the westward march.

Ventus, then Paradigm, rounded SF1. Sweet Grapes held third, but the distance stretched ahead once more. For the run to 8, the wind built into the mid-teens, and the fleet split. Some boats went wing-on-wing, while some opted for spinnakers. Paradigm, Sweet Grapes, Lorelei, and Svea set kites. Paradigm reached far west, both to dodge the ebb and to find proper footing for her asymmetrical, which had little taste for a dead-downwind chase.
Sweet Grapes wrestled briefly with her spinnaker, jib wing-on-wing while the chute was coaxed to life, but once it was flying she drew ahead of Sirius. Paradigm jibed and raced back toward 8, nipping in just behind Ventus.

At mark 8 it was Paradigm, Ventus, and Sweet Grapes in procession. But even in the quiet wind, courage and canvas favored Ventus, who edged past Paradigm in the final run to finish across the line.
Then the numbers told a new story.
The corrected time results had Paradigm in first, followed by Svea and then Surprise!.
And with that, the 2025 Saturday Series was written into the logbook. The overall champion is Surprise!, followed by Svea and then Sweet Grapes. Bravo to every skipper, crew, and volunteer who joined the chase this year. A fine season, a fine finale, and the Commodore’s Cup sails into club history with sunshine, sportsmanship, and stories well worth the telling.
Sausalito Yacht Club Kicks Off 2025 Midwinters
As we left the berth for the first 2025–2026 Sausalito Yacht Club (SYC) Chili Midwinter race on November 3, things didn’t look too optimistic. The four-knot true wind speed and ebbing wakes around pilings confirmed both predictions we’d been watching all week. Listening to the Golden Gate Bridge foghorns as we found our way down Richardson Bay out toward the Little Harding buoy added to our lowered expectations.

Using AIS, we found Mercury, the SYC committee boat, anchored between Little Harding and Point Knox. It wasn’t long before the race committee announced a postponement. There wasn’t enough wind to overcome the ebb as we drifted toward those Golden Gate foghorns.

Gradually the fog lifted, a westerly breeze began to build, and the RC announced they planned to get the race going. A combined start for Spinnaker divisions A and C was announced, along with a 4.9-mile windward-leeward once-and-a-half-around course, using YRA’s Hank Easom buoy as the windward mark and a temporary mark leeward of the start/finish line for the leeward mark.

Most of the 11 boats in the combined spinnaker fleets misjudged the ebb’s strength, and combined with a short start line, were over early for a general recall. The second attempt was more successful, and the spinnaker boats were on their way for a speedy beat to Easom, aided by the ebb.

In the meantime the nine-boat Non-Spinnaker Division started a shorter 2.9-mile, once-around Easom–temp–finish course. They, too, found the ebb helpful on the beat.
By this time a nice 10- to 12-knot wind filled in, making the race swift, even with the strong ebb. All spinnaker boats finished in less than an hour, and almost all non-spinnaker boats in less than 30 minutes.
Back at the SYC clubhouse, racers enjoyed complimentary chili and swapping tales of a race that didn’t look good at the start, but turned out to be a very good introduction to midwinter racing on Richardson Bay.
The next SYC Chili Midwinter race is Sunday, December 7.
ChatGPT Races in the Great Pumpkin Regatta
From helping teenagers write an extraordinary term paper to the elimination of the human race, artificial intelligence has been the hyperbolic cultural and economic phenomenon of the 2020s. Radiologists, Uber drivers and contact center agents all seem to be on the near-term AI chopping block, but what about the sailboat tactician?
Richmond Yacht Club’s Great Pumpkin race is one of the best-attended regattas on the West Coast, with 158 boats registered for the Sunday pursuit race. The format requires rounding both Alcatraz and Angel Island in a single loop, but the entrant can choose the direction. The decision requires a knowledge of the tides, currents, wind conditions and local geography, not to mention basic sailing characteristics. Despite the large number of experienced local sailors, the fleet typically divides into two major groups reflecting a lack of simple consensus.

The author posed this strategic question to OpenAI’s ChatGPT to understand its sophistication on a complex and practical problem. We then had the top two finishing boats review the script and gauge the quality and accuracy of the recommendation.

Ian Charles is the skipper and owner of Maverick, a J/105 competing for St. Francis Yacht Club and finishing in first place. Ian grew up sailing and raced one-design boats ranging from Sunfish and Lasers to multiple J/Boats and Melges. Ian is also a 10-time podium finisher in the Rolex Big Boat Series, and has won multiple one-design regattas in various events.

John Sweeney is the tactician for Will Benedict’s J/105 Advantage 3, representing the Richmond Yacht Club — the second-place finisher. John has competed in three America’s Cup campaigns, serving as main trimmer for America True (2000) and Oracle BMW Racing (2003), and as sporting director for Shosholoza South Africa (2007).
Overall assessment:
Ian: “This was worse than I expected. Beyond it not having access to real-time conditions, it really struggled to put together a coherent course, and as a consequence there is very little usable here. I don’t think AI is capable of answering this question currently; there is not a huge business model for sailing strategy, and it hasn’t received training on this task. As I said earlier, it should have said, ‘I can’t do this,’ rather than hallucinate through the entire exercise. I would give this analysis a 1 out of 10, but interested to see how it improves in the next few years.”
John: “It got the headline correct (it had a 50% chance on this). Pretty much everything else is very confused and/or incorrect. However, it does have a couple pieces of useful information. It just needs to stitch into a coherent narrative. Overall I would rate this analysis 2/10 as an avid AI user. For lawsuits I don’t use chat GPT, except for Google searches. I use Grok for complex problems or law. Zero hallucinations!”

Well, humans win this time, and the tactician’s job appears safe for now, though we all remember when humans used to beat early computers at chess and Go. We’ll check back this time next year.
You can see the prompt and complete commentary from Ian and John about ChatGPT’s efforts as a tactician here.
Who else is using ChatGPT as their tactician? Login to add your comments below.


