2025 Annapolis to Newport Race
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
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.
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.
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.
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.
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