Category: Sailboat Racing

I’d never sailed this far before. The Annapolis to Newport Race—475 nautical miles from the Chesapeake Bay to Newport, Rhode Island—was the challenge I’d been looking for this summer. Aboard the J/42 DIANTHUS, we were racing in a fleet of 14 boats in the PHRF class, part of a larger group of 71 total entries. We expected the race to take about four days.

Friday – Off to a Light Start

Dianthus at Annapolis City Dock
DIANTHUS at Annapolis City Dock

Our start was one of four that day just outside Annapolis Harbor. Winds were light, 5–7 knots out of the SSE. We executed a clean dip start on the third gun, timing the line perfectly and heading upwind while blocking several port tackers trying to squeeze in at the pin.

Looking down the line at the start of PHRF
Looking down the line at the start of PHRF

We short-tacked around Thomas Point Light and chose to hug the western side of the Bay while many competitors went east. As storms built over the Eastern Shore, we found ourselves with better pressure and less rain. By afternoon, we had 8–12 knots and made solid progress. But by evening, the wind faded again.

Dianthus rounding Thomas Point Light
Dianthus rounding Thomas Point Light

Saturday – Rain, Current, and a Spinnaker Sunset

When I came up for my midnight watch early Saturday morning, the boat had barely moved in the still air under a full moon.

Sunrise brought a fresh breeze as we neared the Potomac. We dodged a fast-moving RoRo ship and short-tacked near Cape Charles to stay out of the adverse current.

Rain returned just 15 miles from the Bay entrance—and with it, a total shutoff in wind. As the storms passed, the breeze filled from behind. Soon we were back under spinnaker in 20 knots of wind with a sunset on one side and a rainbow on the other.

We switched to an asymmetrical kite heading toward Chesapeake Light, then changed to the #1 genoa as the wind died again. We drifted toward the light while listening to VHF chatter from a dredging barge surprised to find a “sailboat party” in his spoil area.

Sunday – Into the Atlantic

By early morning we’d rounded Chesapeake Light and were close-hauled in 6–8 knots, tracking north up the coast. By midday, seas had become confused and choppy. As the wind built into the evening, we changed to a smaller genoa and eventually reefed the main. The maneuvers were tricky in the dark, and a couple of us got seasick in the rougher conditions.

Monday – A Leak, A Lull, and some Light Relief

Morning revealed a bit more water in the bilge than expected—eventually traced to a leaking anchor locker. We bailed, let the bilge pump catch up, and got back to full sail… just in time for the wind to shut off again.

For hours, we bobbed in less than 4 knots of wind. With 130nm to go, our hopes of finishing Tuesday morning faded. Now we were aiming for early Wednesday.

Tuesday – Chasing Breeze and Making Decisions

By noon, a few hours of glorious beam reaching had us pointing straight at Newport at 6 knots—but the breeze didn’t last. Afternoon brought rain and hard choices: how to round Block Island. As night fell, we flew the symmetrical spinnaker heading east.

Wednesday – Rounding Block Island and Finish

Just after midnight, we were east of Block Island under spinnaker in winds near 20 knots and boat speeds pushing double digits. Then – bam – a 50° wind shift hidden in fog and darkness slammed us.

We broached.

The boom dragged in the water, the boat laid over, and we slid sideways toward Block Island just 3.5 miles away. A nearby channel marker was the only visible reference.

After a tense few minutes, we regained control and set up for a spinnaker drop—requiring full crew on deck and a headsail hoist before we could safely douse the kite. We reefed and continued, now beating away from danger.

And then… the wind died again.

With a strong opposing current threatening to push us back into open ocean, we made the hard call to go the long way around Block Island. Boats we’d passed earlier were catching up fast.

Our path around Block Island

By sunrise we’d rounded Block and entered Block Island Sound. We hoisted the spinnaker one last time for the final four hours. At last, we crossed the finish line off Castle Hill just before noon.

Docking in Newport, surrounded by anchored boats and fellow racers, we toasted the end of a long, unforgettable journey. Sure, we would’ve liked less drifting and more breeze—but we made it, boat and crew intact.

Huge thanks to Dave and Carol for preparing DIANTHUS and leading the crew. It was a blast to sail with them, along with Wendy, John, and Mike. For my first offshore race, I couldn’t have asked for a more thrilling, humbling, and rewarding experience.

PICTURES | EVENT WEBSITE | RESULTS | RACE TRACKER | VIDEO

By Posted on Posted in Life, Sailboat Racing No Comments Tagged with , , , , ,

We had a classic Chesapeake spring day for the Open House Regatta — cool temperatures, clear skies, and a steady breeze out of the northwest at 6–10 knots. Perfect conditions to spend the day racing on the water.

I sailed aboard the J/99 Battle Rhythm with a solid crew: Chris B, Chris R, Todd, David, April, Jon, and Kevin. This was a pursuit race, which meant the slower boats started first, and the faster boats (like us) started later. We ended up starting near the back of the fleet, side-by-side with Orion, another fast-rated boat.

The course took us from Godfrey Bay into the Piankatank River channel, then out toward Gwynn’s Island. We passed east of Stove Point before turning back upriver and finishing in Fishing Bay. It was a fun, tactical sail — plenty of opportunities to chase down boats ahead and make the most of every shift and puff.

After crossing the finish, the fleet gathered for a raft-up with about a dozen boats tying together — a great chance to relax, catch up with friends, and relive the race. We eventually headed back to the dock and capped off the day with a BBQ dinner at the club.

PICTURES | RESULTS | EVENT WEBSITE | VIDEO

By Posted on Posted in Life, Sailboat Racing No Comments Tagged with , , , , , ,

Over the weekend, our crew aboard the J/42 DIANTHUS took part in a 20-nautical-mile race that started near Thomas Point Light and finished near Miles River Yacht Club. The course took us southeast past Kent Island before turning into the river for the final leg.

We had six on board: Dave, Carol, Wendy, John, Mike, and Jon D. Conditions were breezy throughout, with steady winds over 20 knots and gusts reaching 27. Whitecaps were visible across the Bay, making for a fast and challenging race.

Our fleet was the fourth start of the day. We managed a well-timed reach at the boat end of the line, staying high and clear of traffic. A few of the faster boats eventually came through below us, but we held a solid position early on.

As we crossed the Bay, the course shifted to another reach into the Miles River. We started passing some of the slower boats ahead of us while faster boats from behind caught up. Many boats were flying symmetrical spinnakers—some handling them well, others less so.

When the course turned to a deeper run, we put up our own spinnaker and stayed in control, even with gusts still hitting 25+ knots. We saw boat speeds up to 10.5 knots. Around us, a few boats wiped out in the breeze, but we managed to keep things clean.

Rather than gybe in those conditions, we chose to drop the spinnaker for the final short leg to the finish.

After the race, we rafted up at the club and checked the results: 4th place, just under a minute out of 2nd on corrected time. A strong finish in heavy air and a good day on the water.

PICTURES | RESULTS | EVENT WEBSITE | VIDEO

By Posted on Posted in Life, Sailboat Racing No Comments Tagged with , , , , ,

Friday

Last weekend I headed to Annapolis for the ILCA Atlantic Coast Championship at Severn Sailing Association. With over 100 boats across three fleets, it promised competitive racing—and delivered plenty of challenges. Here’s how the weekend went.

I arrived on Friday and after a quick trip through downtown Annapolis, I arrived at SSA, unloaded and got things ready for sailing.

Saturday

Rain swept through the area in the morning, clearing out just in time for rigging. With skies brightening and a west wind building from 10 to 14 knots – and gustier as the day went on – it looked like we were in for a pretty epic day of sailing on the Chesapeake Bay.

After the skippers meeting I grabbed a few drone shots of the rigged boats across the campus as they started to launch. I got myself launched and sailed 2.2nm out to the course.

About 10 minutes before the first start I went to tune up sailing on starboard for a minute or so, I made a few rig adjustments and tacked onto port. About 20 seconds later—crack—I heard a pop, lost all pressure in the sail  As I heard the top of the mast hit the water next to the boat I balanced the boat as I pulled myself back in.  I had broken the top section of the mast just above the collar where it joins with the lower section. There was a gaping hole with now two ends of the mast sticking out of it.

I grabbed my mainsheet to make a tow line and a few minutes later one of the power boats picked me up for the tow in. Back ashore I quickly took the boat apart, retrieved my wallet and a spare sail and bought a carbon fiber top section to go back sailing with. By the time I got back to the course, the fleet was still mid-way through the first race—delayed by a major wind shift that forced them to abandon the initial attempt.

I joined in the second race of the day. The breeze was now a solid 12–14 knots, with some early whitecaps. I started near the committee boat and had a solid first leg, rounding somewhere around 8th or 10th. But I couldn’t hold position. I lost boats on the downwind and struggled on the second beat, eventually finishing 14th.

Race 3 got off to a strange start. As the fleet neared the weather mark, the buoy broke loose and began drifting downwind. A few boats chased it; others correctly rounded the committee boat, which was now flying the M flag. The race was eventually abandoned after sailing another lap.

The second attempt at Race 3 finally got off clean. By now, depowering the rig was a challenge. The breeze was shifty and strong out of the west—tough conditions to find a rhythm. I gave it my best but couldn’t quite stay competitive, finishing 17th.

The sail in was punishing. The wind had continued to build, and the 2-nautical-mile upwind slog back to the harbor was a workout. The weather buoy later confirmed: we’d raced in upper-teen winds with gusts into the 20s.

Sunday

Sunday’s forecast promised even more breeze and it delivered. By the time the fleet was getting ready to launch the weather buoy was already showing winds into the 20s. I knew the fun factor was not going to be there for me in that wind, so I packed up.  Just before the start there was a gust to 35 before it settled down to 18-23 for most of the days racing.

I made the right decision and went to visit the J/42 that I’ll be sailing on for two upcoming distances races out of Annapolis in the coming weekends.

PICTURES | RESULTS | EVENT WEBSITE | VIDEO

By Posted on Posted in ILCA Sailing, Life, No Quarter Sailing, Sailboat Racing No Comments Tagged with , , , , , ,

We had a beautiful day for the first ILCA Regatta at FBYC this year.  8 boats came for some shifty winds out of the NNW and clear sunny skies.

The first race was a short 1 lap H3 course. The pin was favored and I had a great start just up from the pin while a few boats missed the mark and had to restart. I sailed out to the layline and led at the top mark and held that to the finish.

The second race was similar, I had a great start and pulled ahead on the upwind leg. This was two laps and I led until the final leeward rounding where I flubbed the gybe, put the boom in the water, and capsized while Mike M and Mike C sailed by leaving me with 3rd.

The wind continued to be quite shifty. It would go left and come down the river strongly with some whitecaps. Then a few minutes later it would shift back to the right and get light and patchy. At times there were different winds on different sides of the course, but there was no consistency, sometimes the right had wind and sometimes it was the left.

I sailed the next few races about as inconsistently as the wind itself. I would catch some shifts and other times miss them while others caught them.

Mike M had a great day finishing first or second in every race to win the day.  Mike C was just ahead of me overall and I finished in 3rd for the day.  This was a great tune-up for next weekend’s Atlantic Coast Championship in Annapolis.

Thank you to Holly, Mason, Marc, David, Jen and Jen’s brother for being out there and running our races today.

PICTURES | RESULTS | VIDEO

By Posted on Posted in Life, No Quarter Sailing, Sailboat Racing No Comments Tagged with , , , ,

I joined Battle Rhythm for their first race of the 2025 season—a gusty, northwesterly day that tested our teamwork and shook off some winter rust. We hadn’t sailed together since last fall, and the breeze reminded us of it. On the line with us were Nanuq, Orion, and Corryvreckan. We had a solid crew of nine: Todd, Jennifer, Holly, Lauren, Tina, April, Jon, Chris R., and Dennis.

We got a decent start at the pin, staying low and ahead of the fleet. When Nanuq threatened to roll us, we bailed early and tacked out toward the layline near Stingray Point. Most of the fleet went up the Piankatank, but our gamble to the north paid off. As we approached the weather mark tucked near Jackson Creek, we were less than a minute behind Nanuq, with Orion trailing another minute or two back.

We set the kite and started the long run toward Gwynn’s Island. That’s when things got interesting. During the gybe, strong breeze and rusty coordination wrapped the spinnaker around the forestay—briefly, but enough to throw us off. We got it flying again and pressed on, only to tangle it again as we tried a weather take down at the leeward mark. We then missed the mark, had to re-round, and lost some time.

On the final downwind leg, a northward wind shift made for an awkward angle. A delayed gybe and another wrap left us low on the course, forcing us to luff hard and nearly broach just trying to fetch the finish.

With breeze still pushing into the low 20s and with no injuries or broken gear, we decided we’d had our fill of fun and headed in before race two. It wasn’t flawless, but it felt good to be back on the water shaking out the cobwebs.

PICTURES | RESULTS | VIDEO

By Posted on Posted in Life, Sailboat Racing, Video No Comments Tagged with , , , , , , , , ,

The final sailing day of the year was a blue-bird day of frigid winter sailing aboard J99 Battle Rhythm at Fishing Bay Yacht Club’s Winter Series #3. After the pursuit race against 3 other [crazy] boats we delivered the boat up the Rappahannock to Irvington where it’ll be hauled for the winter.

When I left Richmond in the morning for the trip to Deltaville it was 25 degrees outside. I don’t think I’ve ever scraped ice off a car to go sailing and I’ve never sailed in conditions this cold – not even the limited ILCA/Laser frostbiting that I’ve done. I did come prepared with plenty of layers and all of my heavy weather sailing gear and warm underlayers.

After arriving at the club we all stood in the sun as long as we could before going to boat which sat in the shade given how low the sun is on the horizon at this time. Aboard for the race were 9 of us – Jennifer, Holly, Len, Louise, Abigail, Tina, April, myself and the owner Todd. We had Len at the helm, Todd was up front with April and Abigail and I was in the middle doing tactics and tuning with Holly, Louise and Tina.

The boats we were racing against were Rhapsody, Wendas and Exit Strategy. Being a winter race, there was no race committee so we did a pursuit race around government marks and each boat had their own starting time according to their rating.  As the fastest boat of the fleet, we started over 20 minutes after the first boat to start and 10 minutes after the next closest competitor. The first leg was a bit of a broad reach out of the Piankatank – we set the spinnaker just after starting. Once out of the Piankatank we bore off a little bit for more of a run in the NNW wind of 14-18 knots.  This was definitely a windier day for what we had sailed the spinnaker in and it took us a little while to settle down with the right trim and angles as well as getting the maneuvers clean.

By the time we got to the far mark to turn upwind we were just behind Exit Strategy and Rhapsody. We tacked early to head inshore out of the current and it wasn’t log before we were ahead of both boats and stretching out. I had taken over at the main so I could constantly adjust trim to keep the boat heel and speed up working with Len on the helm. This leg was a little chillier going into the wind and occasionally having some water on deck.  By the time we were approaching the entrance mark to the Piankatank, Wendas was in our sights and still about 1 mile ahead of us when we were at 3 miles to go. The last let was fairly close to the wind and I think we were able to point so much better and held the lay line to the finish. Wendas couldn’t hold the angle we could and got pushed down to Gwynn’s island having to put in a tack to fetch the finish. And with that extra distance we were able to go right around them and finish a few minutes ahead.

Back at the dock we dropped off everyone not doing the delivery and quickly turned around to head up the Rappahannock with Todd, Jen, Holly, April and myself. We did some cleanup/stowing on the way out before we got into the waves and then went around Stingray Point. As we were entering the Rappahannock a tug approached behind us that we needed to avoid by a bit. The rest of the trip was fairly smooth and we were treated to a gorgeous sunset as we approached the route 3 bridge. We cautiously entered Carters Creek in the dark and when we made the turn to the marina we were greeted with a boat Christmas Light Parade.  We were at the dock just after 6, unloaded and left the boat for the haul out.

That was definitely one of the coldest sailing experiences I have had and a pretty one with the sunsets and light parade. Thanks to Todd for having me along for the day and looking forward to warmer weather again next year!

PICTURES | TRACK | VIDEO

By Posted on Posted in Life, Sailboat Racing No Comments Tagged with , , , , , , ,

We had great weather for the final ILCA regatta of the season at FBYC. With 10 ILCA on the line we had mostly sunny skies with winds starting in the 10-15 range and easing down to 5-8 as the day went on. The wind was out the the North so the course was set in the middle of Fishing Bay to have enough fetch, but not be so far away.

I started the first race by being early at the boat, was called over and had to go around the boat to restart. The rest of the day went a little better with mostly middle of the fleet finishes. The very competitive fleet made it so every place was hard-earned racing. Definitely enjoyed having so many people come join. Probably wasn’t my best day on the water after a very long day yesterday and an early morning today commuting to Deltaville from Richmond all weekend.

Thanks to Gene Kendall and his team for running races today.

PICTURES | RESULTS | VIDEO

By Posted on Posted in ILCA Sailing, Life, No Quarter Sailing, Sailboat Racing No Comments Tagged with , , , ,

Jon sailed in FBYC’s closing day race aboard J99 Battle Rhythm with Kevin, Bill, Holly, Todd, and Jennifer.  As is the tradition for closing day, this is a pursuit race with the times calculated based on the distance and the slower boats start first while the faster boats start later. Being one of the faster boats we started about 47 minutes after the first boats to start and we start at the same time as Orien.

The wind was 11-14 at the start and we sailed around until our time came up.  The course was a bit of an out and back into the bay just shy of 20nm.

We started with Orien and sailed to a very short mark just north of the starting line with Orien just to leeward and behind of us. At the mark we tacked for another close hauled course to the entrance of the Piankatank.  The next leg was a reach to the south. We could see that the current was ebbing south and so we took a high line to the north so-as to not sail any extra distance and let the current carry us down.

When we got to the far mark to the south there was a pack of boats just ahead of us. Since we were coming from above and most of them were struggling to fetch the mark, we rounded inside and went right by them.

On this leg we were heading north and would have to tack to fetch the northern mark 2.8nm away.  By this time we were seeing winds as high as 26 and some decent waves rolling down the bay.  We still had a full main and jib and just did our best to work the boat through the waves despite being a little overpowered. Once at the top mark only Wendas was ahead of us when we turn to reach back into the Piankatank. We probably could have carried a spinnaker at this angle, but with winds into the 20s we didn’t try it and nobody behind us did either.

We quickly got around Wendas and reached under full main and Jib as Sting, Afterthought and the J42 all lined up about 150 yards behind us. We kept a close eye on them as they crept up on us and we focused on saying ahead hitting as high as 12 knots through the water at one point.  Once we were in the lee of Stingray Point the wind came down and the angle went a little behind us and we decided to put up the spinnaker. With winds in the teens it was a challenge to control and we almost spun out once. We got the boat under the spinnaker, but would need to gybe once to fetch the finish.  Other boats were setting spinnakers behind us and some were only 5 lengths behind us.

The gybe didn’t go particularly well and we wrapped the spinnaker around the forestay.  Luckly we were close enough to the line that we just went dead downwind spinnaker wrapped and all for the final minute to finish 1st – just ahead of our competition.

We were mostly unaware at the time other than some radio traffic that we didn’t entirely make sense of, but the Trip 27 GOIN’ had a shroud fitting fail and lost the mast out in the bay in the heavier winds. Orien left the race to help, but the club power boat was there to assist by the time they arrived.  Everyone was ok and they got the boat back ashore with a crinkle in the mast just above the deck line and a ripped main.

It was an exciting race and a fun way to wrap up the ‘regular’ season at FBYC.

PHOTOS | RESULTS | VIDEO

By Posted on Posted in Life, Sailboat Racing No Comments Tagged with , , , , ,

Saturday

Saturday’s weather started with sunny skies, temperatures in the 60 and wind around 14 out of the North. We had a good start near the boat in the first race and quickly tacked to port to clearer air. Rick called a great layline and we found ourselves at the top mark behind only Nanuq and Afterthought. We set the A2 spinnaker downwind and had a good run. At the bottom mark we managed to get a jib sheet on the wrong side of the spinnaker which we didn’t realize until mid-tack so we lost some ground having to abandon the tack. The rest of the race was sailed cleanly to a changed weather mark and only Orion got around leaving us 4th over the line and 4th on corrected.

The second race start was a lot more crowded with Tradition trying a mid-line port start. We were a little late in dodging the traffic, but did well to hold our line between Orion and Excitation as we headed up wind. Other than a hiccup with the second spinnaker set, we sailed pretty cleanly in a very competitive fleet. With boats all around us all race we had to settle for a 6th, and were less than 30 seconds out of 4th on corrected time. Sting (J92s) sailed a great race and was on our tail the whole time and we had a few crosses with them. They would end up having to give us room on the pin at the finish and were 4 seconds behind us, but corrected to 2nd.

By the 3rd race the wind came down a few knots and with all of the boats jammed up at the pin, we got out to the boat end to start. From there we worked our way up the right side of the course staying close to Afterthought just to weather of us. We rounded just behind the pack of boats and worked on hitting our targets and numbers. We also cleaned up the timing of our jibes and got it nice and snappy like I used to do on the J70. We would go ono to finish this race in 6th as well and putting us in 6th overall for the regatta. While the result don’t show it, we sailed very competitively and were 1-2 minutes out of 3rd in every race on corrected time.

Sunday

We returned Sunday for what should have been a distance race. Only there wasn’t any wind nor was there forecast to be. After a brief skippers meeting the signal boat and a couple of sailboats went out to explore. Afterthought tried to so some sailing, but there wasn’t enough to consistently keep the sails full. After about an hour racing was called. We were out there motoring around and returned to the dock to do some work aloft and then called it a day.

PICTURES | RESULTS | VIDEO

By Posted on Posted in Life, Sailboat Racing No Comments Tagged with , , , , , ,