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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You come back to your boat after some time away—and find the dolly tire is flat. You could pump it up, and that might work for a while but chances are it’ll eventually go flat again. Most likely, the inner tube has failed. Here’s how to replace it:

What You’ll Need

  • Tire irons (motorcycle-style preferred): Example on Amazon
    You can substitute with large flathead screwdrivers or the handle of a wrench, but be careful – these can damage the tube or rim.
  • Replacement inner tube (4.80/4.00-8 size) with an angled valve stem: Here’s a good option

I recommend using proper motorcycle tire irons—they’re smooth, light, and long enough to give you leverage without damaging the rim or tube.

Tools and materials needed to change a tube

Step-by-Step Instructions

1. Deflate the Tire (if it still has air):
Squeeze out as much air as possible. A completely deflated tube is much easier to remove. If you can’t get to the valve stem to deflate it, you may need to cut it after removing one side of the tire.

2. Remove the Tire from the Rim:
Use your tire irons to work one side of the tire off the wheel. This will take some force, but don’t overdo it—Dynamic Dolly rims are plastic and can bend or crack under too much pressure. Watch the video to see how it’s done.

3. Remove the Old Tube:
Once one side of the tire is free, pull the tube out. Cut it if necessary to make removal easier.

4. Insert the New Tube:
Place the new tube inside the tire, aligning the valve stem with the hole in the wheel.
Tip: Hold the valve stem in place through the hole while you work the rest of the tube into position. Note: there may be two holes in the wheel for the valve stem – only one lines up with the angled stem.

5. Re-seat the Tire:
Carefully work the tire edge back over the rim using your tire irons. Be gentle—don’t pinch the new tube, especially if you’re using improvised tools.

6. Inflate the Tire:
Pump the tire to 10–14 psi, depending on your needs. Make sure the tire is seated evenly all the way around.

7. Install the Valve Cap:
Always use plastic valve caps in a marine environment.
Avoid metal caps—they corrode and can seize onto the stem over time.

8. Reinstall the Wheel on the Dolly.

Disclaimer: As an affiliate in Amazon’s program I may receive a commission for product links.

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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

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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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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

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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

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Fishing Bay Yacht Club opened the season with a beautiful race day for a 12.5 nm course. After a flag raising and skippers meeting,  the fleet headed out on the water. The crew from our sailboat was the race committee today and I was on the mark boat to set the start/finish line. I also had a front row seat to the start and finish and got to fly my drone around the boats when the wind subsided enough while most boats were finishing.

The three fleets started in sequence, sailing out into the bay near the Rappahannock’s mouth, then turning south before heading back to the finish line in the Piankatank River.

Though I wasn’t racing, it was rewarding to help run a smooth event and capture the action from a unique perspective.

PICTURES | EVENT WEBSITE | VIDEO

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The trip that began before it began – with snow forecasted in the days before I was set to leave, I packed the boat a week early so I wouldn’t have to be out in the cold loading everything up.  When the weekend arrived, I was able to brush the snow off the boat – a first for me – and get on the road to Florida.

Driving Saturday was relatively uneventful with no significant traffic.  I made it 10 hours to Daytona got a hotel just outside of the speedway. I went for a run towards the grandstands and saw some of the bike week setup. This place will be packed with motorcyclists a week from now.

Sunday

Since I was only a couple hours from the sailing center, I decided to do a tour of the speedway and I got there for the first tour of the day. The drove us around to see the track and facilities. We got to walk on the track at the start finish line, see how banked the corners are and walk into the grandstand.

I finished the drive and arrived at the sailing center just after 2pm. I drove 870 miles in about 13 hours of drive time.

Very few ILCA sailors were there, just a couple others who skipped the Friday-Sunday event that was just wrapping up in West Palm. Rob E helped me unload. I rigged, tested some camera setups and headed out. On the water I med up with Paul C who was sailing an ILCA-6 while I was in an ILCA-7 and we spent an hour going upwind and down on our own made up course with .5 mile legs.

Back ashore I derigged the boat and few of the sailors from West Palm started arriving and unloading. As the sun set I put the drone up to get some pictures of the sailing center.

Monday would be spent working remote from the hotel on what would mostly be a rainy day.

Tuesday

By Tuesday morning 86 boats had assembled for the first day of racing. Following a skippers meeting we launched and headed out to the course in some pretty good wind out of the north at 15-18 knots.

First race I had a slightly late start at the boat and went out to the right in clear air. I stayed to the right rather than crossing most of the fleet and getting to the left as the wind went that direction and found myself at the top of the bottom 1/3 of the fleet at the top mark. I picked up a few spots around the course to finish 25.

We started the next race and I was again at the boat and went right. There was a huge lefty and I got clobbered up the first beat.  Halfway down the run something wasn’t right, boats ahead weren’t rounding and then the marks were picked up. They had abandoned the race on account of the wind shift and never started the ILCA-6 fleet. Was a shame to spend all of that energy on a windy day on half a race, but at least we’d have a better chance at a better result.

For race 2 we stared under the Y flag. I did a good job winning the boat and again stayed right and carried it as far as I could.  Then I made my way back left with just a few other boats with me and punched out, and James Jacob just a little more left of me. As we got to the top mark we were the first two there and traded tacks. He got to the windward mark first, but had to round wide and I got the inside as we went to the offset mark where I rounded first. James and another boat went a little more down the right side of the course as I stuck to the left and I managed to hold my own rounding the gate in 4th as some of the faster boats started to catch up. Unfortunately, from there I’d make a few mistakes on the beat and lost about 10 boats – settling for 14th.  Still a respectable finish and certainly the highlight of the weekend to lead a race at least for moment.

By the 3rd race of the day I was pretty tired. The wind was still blowing and we had to wait a while for the radials to finish. When they did try to start us, they blew it off just before the start to reset the line. Once reset, a race was started and I started at the boat again and went right finding myself in good company with James and Mark B. Luckily the wind went right and we were in the top group. I didn’t have the strength to hike on the very long leg and was just out of the top 10 at the first mark. I mostly held my position and dropped only a couple positions for a 15th place finish.

Wednesday

Wednesday was a lighter day and we sailed out and postponed for an hour. Once some wind in the 8-9 knot range did come in, they got us started and I had a terrible start right between Don H and Patrick W who rolled right by me and left me in bad air. I just worked on finding clear air and picking shifts and did well to climb back into the middle of the fleet. By the second leg I was up to almost 10th, but lost a couple boats downwind and finished 16th.  Great result given the start.

In race 5 I had a terrific start on the middle left of the line and carried that to the left – only it was too far and I missed some opportunities to get back right when the pressure and shifts were there. Made a couple mistakes to slow myself down coming out of the leeward gate, never got it going to pass anyone and finished 32.

By the final race of the day the wind had eased to 6-7 knots of wind. I was pretty late starting at the boat and just watched everyone sail by. Never felt like I could get in pressure and get the boat going and settled for a 26

Thursday

On Thursday the forecast was for no wind. We arrived to no wind, saw no wind, had no reason to believe wind was coming and after postponing onshore for about an hour, racing was called for the day. I did a run in the park near the sailing center and headed back to the hotel for some work before joining a group of D11 sailors for dinner.

Friday

With no racing yesterday, the start time was moved up to 0930 and 4 races were planned. At that time in the morning, the light on the course is fantastic. The wind was 10-11 as we headed out, but quickly fell to 7-8 as racing started. There was current sweeping us over the line and it was reset a time before we got a clean start under black flag. I didn’t time the start well and was in the back of the pack all the way around the course and finished that way.

After waiting for the radials to finish their race – they weren’t started until we were almost finished – I was determined to get a better start. I was right on the line near the middle right on time with a good lane and a few boats around. Unfortunately, the mainsheet slipped out of my hand – I saved myself from flipping to windward, but parked the boat for a second. I still had somewhat of a lane and was just about to tack to port into a hole when the boat just to leeward and ahead of me started yelling for me to tack. I wanted to hold my lane for a just little longer before tacking, but (conversations after racing would confirm) he seemed to think he was entitled to tack since he thought I wouldn’t want him leeward/ahead even though I had right of way and he wasn’t really affecting my wind. And so he tacked forcing me to duck him in order to not T-bone him and the hole I had hoped to tack into was gone. I immediately protested, he didn’t turn and he ended up dropping out just before the protest was to be heard. I would sail the rest of the race in the middle of the fleet finishing 29th.

For the 3rd race of the day – I again got shot out the back. Only solace was starting to figure out where the lane of wind was and the patterns to the shifts. I picked up a few boats as I went and finished 26th.

The final race of the regatta would start the worst and finish one of my best. I was late to the boat and due to traffic took hitting the committee boat (stand off buoy) over tussling with other boats. After I did my turn and started the race behind almost everyone, I had a great view of the wind from the boats ahead. I set to work in the lane of wind I discovered in the prior race and picked off 10-12 boats in that first upwind leg. I’d do it again in the second beat and got up to 16th by the finish.  Imagine where I could have ended up with a better start.

I ended up 25th overall and the second Apprentice Master. It was a nice trip to experience some warm weather, see a new venue and spend a week of sailing with some ‘old’ friends.

PICTURES | RESULTS | VIDEO

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