Racing in Penn Cove is always a treat, and this year’s Whidbey Summer Classic Regatta (WSCR) hosted by Oak Harbor Yacht Club truly was Penn Cove at its best.

Since its inception in 2021, the premier class at WSCR has been the San Juan 24 (SJ24) fleet. The event has drawn enough SJ24s for a one design fleet every year, including hosting the 2022 San Juan 24 North American Championships. The SJ24s were not the only boats out for the 2025 edition of the WSCR, however. Also sharing the waters of Penn Cove were two PHRF racing classes with a wide span of ratings from a J/111 rating 48 to a Santana 20 rating 240, as well as a non-flying-sails Cruising Class of five boats.

The favorite to win the SJ24 class was Juan Solo, a local Oak Harbor boat, which has topped the one-design fleet’s podium four years running. Juan Solo is the boat I race on, but this event was special; it was my debut as a skipper at a buoy racing regatta. The absence of our regular skipper—Gabe Hill, who was away at his wedding—opened things up so any boat in our fleet might take home the win.

Chosen Juan was the likeliest challenger. Skipper Eddie Smith has been gaining ground on Juan Solo every Thursday in our local club races already and, with an accomplished SJ24 crew aboard, Chosen Juan would be ready to pounce on any opportunities. 

The fleet got underway on the first of three days of racing after a short postponement to allow a nice southwesterly breeze to settle deep in Penn Cove. The breeze was forecast to die before building as it shifted to the west, so the fleet all elected to raise #1 genoas. This was my most confident day of the event, since we had two of our normal crew, Chad Saxton and Raven Vick, onboard. We got away cleanly and our Juan Solo crew rounded the weather mark first. Finding a ribbon of pressure and managing to stay in it while the rest of the fleet got stuck in the decreasing breeze, we were able to extend and take the first race.

The mistake from Juan Solo and its new skipper that the fleet was looking for came almost immediately. After switching to the #2 in a building westerly for the second race, we rounded the first mark in second behind Obi Juan, a Bellingham SJ24 skippered by Brian Pernick. Obi Juan (formerly named Econo Juan) is a fast boat and a multiple time SJ24 North American Champion. After a great downwind leg during which we were able to pass Obi Juan, we were clear ahead at the leeward mark. Genoa up, kite coming down, and, “BANG!” The jib fell slack and we all looked up in horror as our only jib halyard ran down the mast after snapping at the shackle. A quick retirement allowed us to survey the damage, but the answer was obvious, this was a repair that had to be made at the dock. After a quick discussion with the crew, we decided to race the last race of the day with our genoa on our spinnaker halyard. The decision was a good one, as we took home a third place finish.

Obi Juan topped the leaderboard after day one, with a consistent 3, 1, 2 scoreline. Fellow North Sound sailor Fred Ames’s It’s the Juan cruised into second with 7 points, we were third with 10, and our friendly rivals on Chosen Juan were fourth with a scoreline of 11 that belied their speed A  couple of unfortunate hiccups—sailing though the closed start line in one race and misreading the course board in another—left them with higher scores than their race day would otherwise have suggested.

Back on the dock, the repairs were on. Raven went up the mast, and nearly two hours later, we had successfully rerun and respliced our jib halyard. Everything was set for day two, and we had our work cut out for us in this competitive fleet.

The second day of the regatta featured a brand new, and less familiar, crew for Juan Solo. Recent Anacortes High School graduate Cameron Furin and former University of Washington sailor Austin Hauter were aboard. We debated our headsail choice all the way to the start line, while finally settling on the #3. The wind that would normally have better fit the #2, but we decided that a crew that hasn’t sailed together would be better served with a simpler sail plan. 

The sail choice turned out to be perfect. Despite being underpowered if the wind dropped at all, our quicker tacks and higher pointing angles made up for the slight loss in speed. We gained positions in every race that day, finishing second and first in the day’s early races. Despite the solid results, we decided to switch to the #2 for the final race of the day. After a good start and first couple of legs, we prepared to wrap up the run, round the leeward mark in second, and head to the finish. A knot in the spinnaker halyard had other ideas, however. We endured a very messy rounding, and wound up finishing the race a disappointing fourth.

After two days of racing, the top four were separated by only three points. Obi Juan continued to lead the way, we were one point behind them now on Juan Solo, one further back was Chosen Juan, and It’s the Juan was now fourth but still very much still in contention. The entire regatta would hinge on two Sunday races.

Light wind greeted the fleet on Sunday. Chad, Raven, and Cameron were aboard as we looked to extend our WSCR winning streak to five years. Juan Solo, Chosen Juan, and Obi Juan all started well, but I made an ill-advised early tack away from the fleet and rounded the weather mark second behind Chosen Juan, a result that would hold to the finish. Obi Juan finished in third, tying the top three boats and setting up a winner-takes-all finale in the final race.

The fireworks started immediately in the prestart. Inside the last three minutes of the prestart I executed a double tack to kill time, but due to the light wind I was nearly stopped as I exited my second tack on starboard. Smelling blood, Chosen Juan dove to my leeward side and attempted to luff us up. I tried to avoid them, but contact occurred between my outboard and his bow. Both boats broke away and protested, and the race was on. Sailing with adrenaline, we sailed well on the beat and walked away from the fleet, maintaining a solid gap for the first three legs of the race. The final run was a different story, though, and Chosen Juan followed more pressure down the right side of the course, passing us in the final few boat-lengths of the race.

Tension was high in the yacht club as we awaited the results of the protest hearing. Nobody likes for the regatta to be decided in the protest room, but that’s where we found ourselves—the team that won the hearing would win the regatta, the other would finish third. It was a contentious but respectful hearing, and after deliberation the protest committee determined that Chosen Juan had not given me sufficient time and space to respond to him gaining right of way. We had won the regatta, and Juan Solo kept the WSCR streak alive!

Tight racing among friends was the theme of the weekend, with three of the four fleets determining their winner in the final race. Dan Randolph and Farr 30 Nefarius took the win in PHRF 1, followed by Mike Cain’s J/105 Panic and Ben Braden’s UN30 6 Feet More. Local boats swept the podium in PHRF 2, with Chad Holcomb and Olson 25 Bigg Dogg leading the way followed by Gary Stuntz in Santana 20 Just Ducky and Larry Munns in Jeanneau 42DS Pearl JEM. Bill Weinsheimer and Islander 32-2 Excitement took home the win in the cruising class, followed by Paul Belanger’s Ericson 27 OTTER and Brian Vick’s Catalina 25 Lemonade to round out the podium.

Join us next summer for the sixth annual Whidbey Summer Classic Regatta for some more happy times under sail in Penn Cove!

Full results at: www.whidbeyclassic.com/