Tag: Annapolis

Annapolis Maryland

The Annapolis to Bermuda Race is a 753-mile offshore race that begins with approximately 120 miles down the Chesapeake Bay before turning east for another 630 miles across the Atlantic to Bermuda.

Our race weekend began in Annapolis with the Eastport Yacht Club’s skippers’ briefing. That evening we took Bay Retriever out for one final practice sail before gathering for a crew dinner, watching the sunset over the harbor, and finishing the last of the provisioning. After weeks of preparation, everything was finally ready.

Bay Retriever is a 2019 J/99, one of the newest and smallest boats in the fleet. Although only 33 feet long, the J/99 was designed specifically for offshore racing, with a simple sail plan and equipment built for long passages.

This wasn’t the boat’s first offshore challenge. Bay Retriever had already completed the 2024 Annapolis to Bermuda Race, the 2025 Annapolis to Newport Race, the Around Long Island Race, Block Island Race Week, and thousands of miles of additional offshore sailing.

Our crew of five brought a wide variety of experience. Sean has sailed to Bermuda multiple times and has years of experience as a professional sailing instructor and delivery captain. Ian combined offshore experience with dinghy racing and J/105 sailing. Cameron had sailed nearly every one of Bay Retriever’s 9,000 miles. Jon has extensive Laser experience and time on a J99 as well as completing last year’s Annapolis to Newport Race.

With 13 boats in our class, we knew our biggest competition would come from boats sailing at similar ratings, while several larger boats would likely finish well ahead of us.

FRIDAY

Race morning brought calm conditions and plenty of excitement around Annapolis Harbor. Spectator boats filled the water, the Pride of Baltimore was nearby, and family and friends watched the livestream from home.

Our plan was simple: start conservatively, and sail our own race. Instead, everything came together even better and Bay Retriever won the start at the committee boat end of the line, putting us immediately into clean air and allowing us to choose our own course through the light breeze at the top of the Chesapeake.

The forecast called for light upwind sailing down the Bay before reaching the Atlantic sometime the following afternoon.

As darkness fell on the first day, we were passing Solomons Island and settling into our watch schedule. Sean and I stood the first overnight watch while the rest of the crew tried to find sleep aboard a heeled-over race boat.

SATURDAY

By sunrise we were off the mouth of the Rappahannock River, making good progress south while the breeze held. We knew lighter conditions were expected later in the day, so we took advantage of every bit of wind we could.

Eventually the forecast caught up with us.

Near the mouth of the Chesapeake, the wind faded dramatically. Current became the dominant factor, and progress slowed to a crawl. At one point we even deployed the anchor in an attempt to avoid being swept backward. Whether it fully set or not, it reflected just how little wind remained.

The final miles out of the Bay became a frustrating series of tacks through shifting current and light air. What might normally take far less time stretched into nearly 30 hours before we finally cleared Cape Henry and entered the Atlantic.

Once offshore, the breeze steadily returned. We hoisted the Code 0 as the sun began to set and worked our way through commercial shipping traffic entering and leaving the Chesapeake.

Gradually the constant chatter on VHF radio faded as the shoreline disappeared behind us. The boat settled into a comfortable rhythm, and for the first time it truly felt like we were offshore.

SUNDAY

The wind increased into the 20-knot range, and the seas built quickly as we approached the Gulf Stream. Much of the day was spent reaching under a triple-reefed mainsail and jib, occasionally surfing down waves at speeds approaching 18 knots. The motion below deck became challenging, and not everyone escaped the day feeling their best.

MONDAY

Monday morning began with a squall slowly building on the horizon.

As it approached, we reduced sail until we were carrying only a triple-reefed mainsail. Heavy rain swept over the boat while lightning flashed in the distance. Once the squall passed, it carried the wind away with it, leaving us briefly drifting in light air before the breeze gradually returned. By afternoon we were back under the spinnaker and making good progress once again.

TUESDAY

Tuesday, our final full day at sea, provided the reward after several days of changing conditions. Sunshine, steady breeze, and relatively flat water combined for fast, comfortable sailing toward Bermuda.

That evening the first lights of the island appeared on the horizon. Through the night we watched Bermuda slowly emerge from the darkness beneath a sky full of stars.

WEDNESDAY

Just after dawn, we called into Bermuda Radio who let us know about several cruise ships and the tall ship Sagres entering the harbor.

At 6:51 a.m., Bay Retriever crossed the finish line, completing 753 miles of racing.

After congratulating one another, we lowered the sails and motored around the island toward Hamilton, tying up at the Royal Hamilton Amateur Dinghy Club.

With the race complete, we enjoyed a few drinks dockside before clearing customs, cleaning up, and heading into Hamilton for our first meal ashore. That evening, sleeping in an Airbnb after nearly five days aboard the boat felt especially good.

THURSDAY, FRIDAY

Arriving on Wednesday left us with two full days to enjoy Bermuda before heading home.

We explored the island’s towns, beaches, and historic forts, watched a local parade, sampled plenty of great restaurants, and made sure to try both Dark ‘n Stormies and Rum Swizzles along the way.

SATURDAY

The week concluded with the awards ceremony, dinner, and celebration at the Royal Hamilton Amateur Dinghy Club.

PICTURES | RESULTS | EVENT WEBSITE | TRACKING | VIDEO

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The Magothy River Sailing Association’s Spring Fling brought a difficult mix of light air and strong current on Saturday, reshaping what was intended to be a distance‑style triangle race just north of the Bay Bridge. The J/99 Bay Retriever made the trip up from Back Creek to take part in the event, which allowed boats to start at any of three marks and sail the course in either direction within a set time window.

Early forecasts suggested steady breeze and manageable current, but conditions shifted as the morning progressed. The leftover chop from an earlier 10-15 knot breeze remained, even as the wind faded.

Bay Retriever enjoyed the last of the usable wind during the hour‑and‑a‑half sail to the southernmost mark, sailing mostly upwind and against a strong southerly current. By the time the crew began their race around 11 a.m., the wind had dropped significantly while the current continued to run hard.

The team chose the counterclockwise option, which required two close‑reaching legs partly into and across the current before a downwind leg with the current toward the finish. With only 3-6 knots of breeze, lingering chop, and a strong opposing flow, progress was slow from the outset. After about ninety minutes, it became clear that the first mark was still roughly two hours away, making it unlikely the full course could be completed within a reasonable timeframe.

The decision was made to retire from the race. Once headed home, the crew set the spinnaker in an attempt to keep the boat moving, but even that wasn’t enough in the fading breeze. The kite came down shortly after, gear was packed away, and the rest of the trip back was under power.

Despite the early exit, it was still a welcome return to the water and a chance to shake off the offseason. With spring underway, more racing – and hopefully more wind – awaits.

PICTURES | VIDEO

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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

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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

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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

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Saturday

The forecast for day one at the Sunshine Open ILCA Regatta at Severn Sailing Association in Annapolis wasn’t very good. After the skippers meeting, we postponed ashore for 25 minutes or so until we started to see a little bit of wind to sail in out in the harbor. It was cloudy and overcast with a very light air forecast. The cloudy conditions helped keep the power boats away enabling us to sail in the Severn River on a short course.

On the deck at Severn Sailing Association during the Skippers' meeting of the Sunshine Open.
Skipper’s meeting with little wind

The wind was out of the west and current was coming right out of the Severn River down the course. At the first start I misjudged my timing to the line on account of the current and ended up being late and 3 rows deep. I crossed behind almost everyone and did my best to go fast and find pressure arriving at the top mark around mid fleet. I managed to catch a couple boats on the downwind and after 2 laps finished 10th.

In the second race, I had the timing for the start about perfect and had Dave just below me and only Craig between me and the boat. Craig tacked out early; I kept going for a few more lengths before tacking out into pressure. Craig and I went up the first 1/3 of the leg on the right while most of the fleet was to the left. I started picking puffs and shifts and by the top mark I was a good 150 yards ahead of the guys behind me. I played it a little too conservative on the rest of the course and wound up getting passed on the next two legs, finishing 6th, as the wind started to taper off and the current picked up.

Without a good prospect for more wind we were sent in. James won both races and sits in first with Dave just behind him. Then there are 4 boats within a point of each other and a few more points back to another couple boats and me in 9th.

Tomorrow’s forecast is looking for good wind, but likely rain all day.

DAY 1 RESULTS

Sunday

Rigging in the rain for day 2 at the Sunshine Open at Severn Sailing Association.
Rigging in the rain for day 2 at the Sunshine Open at Severn Sailing Association.

Arrived for day 2 of the Sunshine Open at Severn Sailing Association in Annapolis to plenty of rain and even a little thunder. It looked like most of the weather coming was going to be light but likely to persist into the early afternoon. We launched on time and sailed in area C at the mouth of the Severn River.

After a short postponement we got racing in 8-12 knots of wind. For the first race I started at the boat just a tiny bit late and was able to rack out to the right into what looked like some better pressure. By the top mark I was in second just behind Bob T. Downwind I went low and easily passed Bob and extended. On the next upwind I held my position with James, Dave and others just behind me. I didn’t keep the boat going early in the final downwind and 4 boats went right around me leaving me in 5th.

By the second race the wind had picked up to 10-13 and my not so great start at the pin left me just in the top 10 at the top mark. As we went downwind the wind started to ease a bit. I went left seeing the wind going that way as it continued to ease while the rest of the fleet went mostly right. The wind got down to 4-6 and with the left over waves on top of the left to right current made going upwind a real slog. The left paid and I was in 3rd just on Luke’s stern with Dave just ahead of us. The downwind took forever but we finished in those places putting me in 3rd for the race and bringing me up to 5th overall. It had looked like they were going to shorten course for us and they eventually did for the radials sparing them from having to sail downwind again. With little wind we headed in. Congratulations to Dave who was able just ahead of James to win the weekend. It was fun sailing in the top of the fleet with Ted, link, Craig and others. Thanks to Scott, Kat, Gavin and everyone at SSA who made the weekend possible!

FINAL RESULTS | PICTURES | EVENT WEBSITE

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J99 Battle Rhythm at Bert Jabin's Yard in Annapolis.
J99 Battle Rhythm at Bert Jabin’s Yard in Annapolis.

For the delivery of Battle Rhythm to Deltaville we had some unfavorable weather for our original plan yesterday which allowed me to jump on the race committee for the Down the Bay Race start. After another night in Annapolis we had an early start on Saturday. Battle Rhythm is a 32′ J99 sailboat #94 and was docked at Bert Jabins near Annapolis.

Battle Rhythm under spinnaker.
Battle Rhythm under spinnaker.

Once we were off the dock and into the Chesapeake Bay, we did a quick instrument calibration and then headed south around Tolly and Thomas Points. We started with good wind on the beam and with just 4 of us onboard we got the spinnaker up and were seeing 7.5 to 9 knots under spinnaker. Eventually the wind eased and we dropped the spinnaker and motor sailed again. When we were close to the mouth of the Patomac early in afternoon the wind again built and we raised the spinnaker again.

Eventually the wind dropped off to almost nothing and moved forward so as the sun was setting we struck all the sails and just motored the rest of the way to Deltaville. We arrived just after 9pm with a total trip time of 13 hours and just over 8.5 hours of motoring.

PICTURES

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On the signal boat for the start of the Down The Bay Race
On the signal boat for the start of the Down The Bay Race

I am in Annapolis with some time to spare before helping with a boat delivery tomorrow so I was able to join the Race Committee for the start of the Down The Bay Race. There were at one point 38 boats signed up, but given the windy and potentially storm conditions of this afternoon – a large number of boats dropped out with only 14 making it to the start. We started out in the bay just outiside of Annapolis at a mark known as R2. Visibility was only a couple miles and the wind was 12-16 out of the south. We rolled through the starts and got the boats going and I took a few photos.

Start of the first two PHRF fleets in the Down The Bay Race.
Start of the first two PHRF fleets.

EVENT WEBSITE | PICTURES

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I know a regatta and an ECU football game in Annapolis is a rare thing and so today I was able to sail in the Laser District 11 Championship and attend ECU’s away game at Navy.  It was cool to see all of the midshipman in the pregame ceremonies and the flyover. It was downhill from there for ECU football loosing 42-10.

PICTURES

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Saturday

Severn Sailing Association hosted the Crab Claw Regatta and 2019 Laser District 11 Championship Regatta.  It just so happened that East Carolina’s football team was playing at Navy this afternoon so I figured out how to do both.

The skies were overcast with temperatures in the high 70’s and the wind out of the North at 11-13.  I sailed the first two races in some lumpy seas making it critical to keep the boat flat to go fast upwind.  There were some shifts to hit as well.  Downwind it took a while to figure out how to catch the waves – by the 4th time I went downwind finally started to figure it out just before I headed in.

The fleet did 2 more races while I headed in to attend the ECU vs Navy football game.

I’m in 20th after day one and hope to improve once I can drop 1 of my DNS’s.

DAY 1 RESULTS

Sunday

Day 2 of the Crab Claw Regatta and Laser District 11 Championship at Severn Sailing Association in Annapolis and we were greeted light winds and a postponement ashore while we waited for the wind. It came soon enough and along with the clearer skies we ended up with 12-14 knots of wind out of the North. We were out in the north sailing area looking upwind at the bridge.

In 3 races I had pretty good starts usually winning the boat or close to it and crossed most of the fleet on the first upwind. I didn’t quite have the upwind speed as some of the fast guys, but held my own when I remembered to round the offset and didn’t hit any marks. By the 3rd race I started to get the boat dialed in a little better and had better speed and didn’t make any mistakes leading to my weekend best of a 4th. Ended up 15th overall and it was great to sail with some competition to tune up before the FBYC Chesapeake Bay Laser Masters in October. Luke, Eric, Mike, Scott and Dave all sailed great this weekend and were fast all the way around the course. Thanks to Scott, Dorian and the fleet for hosting!

One other bit of news coming out of the weekend – Scott Williamson is going to take over as the District 11 Secretary. It’s a post I’ve held since the end of 2006. The Laser fleets in the mid-Atlantic remain a great group of sailors and it’s been fun to see the ups and downs of the fleets and to help play a part in connecting sailor and getting them out sailing. Thanks for taking this on Scott and I look forward to continuing to see the sailors I’ve met throughout the district for many years to come.

PICTURES | RESULTS

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