
A relatively small but very friendly regatta, the Bluegrass Sailing Club hosted 8 boats to compete in their second annual Bourbon Regatta Sail-Fest. Light winds dominated the early October weekend, which did not favor the brothers, but friendly and helpful competition made the event special. This is a regatta the Brothers have an emotional tie to: our mother’s parents lived just 25 miles south of Kenlake State Park back in the 1980s.
Brother Kevin arrived early with the boat and created a video on setting mast rake. And then, of course, we couldn’t quite point with everyone else, so something was off on our mast rake setting. That said, analysis of the videos show that we also had the halyards way too tight: air was not flowing well over the luff’s of our sails. So many things to think about when setting up your boat, and then on the race course.
Five races were scheduled, and five races were held over 2 days. Although the fleet was small, the competition was well prepared for these light winds. Races 1 and 2 were sailed in about 4-5 knot winds, and dropping; so low that Race 2 was shortened to once around the W/L course. Despite our best efforts, Pura Vita (Vogler) took 2 bullets Day 1 setting themselves up well going into Day 2.
We got an early start Day 2 to ensure we could get 3 races in. Although winds were extremely light, we left the harbor before 8 AM. Our friends on Kentucky Lady (Montague) decided to sail out of the harbor on jib alone, and raise their main out in the main lake. Something stuck at the top of the mast, and they called for help on the radio to minimize the time to repair. Gadzooks! to the rescue! We sailed over, pulled Kentucky Lady over on top of our boom, and realized the shieve at the top of the mast had fractured, preventing the halyard from raising the main. We hand-raised the main, locked the halyard in, and pushed the boat upright. Here’s a short of us completing the maneuver. The RC took the snapshot a the top of this post for us.
After some postponement where a few of us got into water fights, racing got underway. Pura Vita took another bullet, with the Brothers close behind. Winds were strange: there were several flat spots on the water, but wind was still there, making it tough to read. Fast forward to the final race, the wind, which was forecast to shift big-time to the left, finally oscillated between the old and new winds, making the windward mark a bitch to get around.
In the end the Brothers tied their results to last year, coming in 3rd overall. However, only 1 point total separated first, second and third. We simply lost the tie breaker (again). That said, we sailed a very consistent regatta with a 2, 3, 2, 2, 3. We just needed one bullet to take a first overall, and alas it was beyond us this time.
Here are the regatta scores:

There were times when the rear camera wouldn’t work, and of course we didn’t really even know it until after the day’s racing. And, one race we were completely unaware that neither camera worked. But we captured 4 races, or at least parts of 4 races. Enough to learn a thing or two. Here’s the playlist on YouTube.
Here are a couple of things we learned from the videos:
- Halyards were too tight all weekend. You gotta look at the luffs.
- We led all of Race 1 until the finish line. We completely screwed up identifying which end of the line was favored, AND on top of that did not stay between our competition and the finish, letting him get by and steal the bullet from us.
- Our starts weren’t too bad, but then again it was not a crowded line. However, in at least races 1 and 2 we allowed ourselves to get pinned at the pin end. We were still able to cross, but we should not have bee that close and without room to maneuver.
- Brother Kevin needs to listen more to Brother Kendall about where to go. We did a jibe set on Race 1 based on Brother Kevin’s call, and should have followed Brother Kendall’s call for a bear-away.
- For some reason we were not able to point. Likely it was a mast rake issue. We will have to look more closely at this.
This was our final regatta of the year. Brother Kendall will be undergoing a major medical procedure in late October and needs recovery time. And, Brother Kevin has many things to complete before winter hits in the midwest. We intend to be back on the water at the George Washington Birthday Regatta in mid-February at Lake Eustis Sailing Club. Until then, Gadzooks! will get a bottom refinishing, and some new rigging, as well as a new jib. We have a full sailing schedule already planned out for 2025, and will discuss in our Season Reflections post.
Until then, watch our YouTube channel, as well as the Sailboat Instructor channel on YouTube, run by our friend, Eric on Wildcard (Flying Scot 6135). We will have some videos to be posted about how learn from video captured during racing. Until our next regatta, we wish you and yours smooth waters and fair winds!

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