2026 Islander Regatta
The Islander Regatta had been on my radar for a few years, and I finally had the opportunity to participate. The regatta is a human-powered circumnavigation of Gwynn’s Island in Mathews, Virginia. I frequently sail and paddle around Gwynn’s Island, but making it all the way around in a small sailboat or on a paddleboard is usually a little farther than I’d want to do on my own. Doing it as part of an organized event made it a great opportunity.
The event started from the Islander Hotel at 8:00 a.m. on Saturday. The hotel is another place I’ve passed countless times by both road and water but had never visited. It operated until 2003, when it was heavily damaged by a hurricane. The building and surrounding property have seen only occasional use since then.
Around 80 participants launched from the beach in a variety of human-powered boats, including sea kayaks, recreational kayaks, paddleboards, rowing shells, and other craft, all setting off on the counterclockwise trip around the island.
After leaving the beach, we rounded the hotel property and entered the channel leading toward the bridge. Once under the bridge, we headed into Milford Haven on the west side of the island. As the water opened up approaching Hole in the Wall, the wind increased and the longer fetch built up small waves that struck from the side. That meant a lot of paddling on the left side to compensate for the wind and waves.
At the southern end of Gwynn’s Island, participants had a choice. Some elected to portage across the beach, cutting about a mile and a half from the route. Roughly a quarter of the boats, including mine, continued around the entire island without taking the shortcut.
Once we reached the eastern side of the island and entered the Chesapeake Bay, the shoreline provided more protection from the waves, and the wind eased considerably, especially along the stretches lined with trees and houses.
At the mouth of the Piankatank River, we turned west into the wind for the final leg of the trip. The last 2½ miles back through Hills Bay to the Islander required paddling into a light headwind and small waves before returning to the finish.
2026 Annapolis to Bermuda Race: 753 Miles to Bermuda
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
2026 Tour de Chesapeake
Saturday I joined a group of eight riders for my first Tour de Chesapeake, a bike rally that winds through the back roads and alongside the waterways of Mathews County, Virginia. Over the course of 55 miles, we traced a route that showcased the county’s mix of farmland, forests, and coastal scenery. For a first‑time experience, it was a great introduction to the event and a fun way to explore coastal Mathews County.
2026 MRSA Spring Fling
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.
Aging Gracefully on the water: How ILCA Masters Sailing Has Shifted Over 25 Years
For the past 25 years, I’ve had a front‑row seat to the evolution of ILCA Masters sailing at the Chesapeake Bay ILCA Masters Championship. First it was as an event manager when I wasn’t old enough to sail and later also as a competitor when I could join the fleet. Watching the fleet change over that span has been interesting, not just for what it says about our sport, but for what it reflects about broader trends in sailing across the country.
This particular event isn’t meant to represent every region or every fleet, but it serves as a revealing microcosm of a national shift that’s been unfolding quietly and steadily. The data tells a clear story, and the patterns behind it offer insight into how the sport is aging, and what forces may be shaping the Masters landscape today.
Looking at the rank distribution from 1999 to 2025, the trend is unmistakable: the ILCA Masters fleet is getting older.
In 1999, the Apprentice (then 35-44) and Master (45-54) categories made up 63% of the fleet. By 2025, those groups – now 30-44 and 45-54 – represent just 39%.
Meanwhile, the Grand Master (55-64) and Great Grand Master (65-74) categories have steadily expanded, now comprising more than half of all sailors. And the newly separated Legend (75+) group has grown to 8% of the fleet.
Also note the minimum age for Apprentices shifted from 35 to 30 starting in 2022 and legends were broken out from the Great Grand Masters starting in 2021. 2025 was the first year of separate ILCA 6 & 7 starts.
Why the Shift is Happening
Several forces – cultural, economic, and demographic – are shaping this long-term transformation.
Longevity in the Sport
Sailing is uniquely suited to lifelong participation. Unlike many sports where age quickly becomes a limiting factor, ILCA sailors often remain competitive well into their 70s. Experience, tactical awareness, and boat-handling finesse often outweigh raw athleticism.
Better Health and Fitness
Today’s older sailors are healthier, fitter, and more active than previous generations. Advances in training, nutrition, and medical care have extended the competitive lifespan of athletes across many sports, and ILCA Masters sailors are benefiting from that trend.
Community and Camaraderie
Masters regattas are more than competitions – they’re gatherings of friends who’ve shared decades on the water. The social fabric of these events is a powerful draw, keeping sailors engaged long after their “peak athletic years.”
Barriers for Younger Sailors
For sailors in their 30s and 40s, life often gets in the way. Careers, young families, and financial pressures make it harder to travel to regattas or commit to a full season. The Apprentice category’s decline reflects these realities.
What This Means for the Future
The aging of the ILCA Masters fleet is not a crisis, but it is a trend with implications. Older sailors bring depth, experience, and stability to the sport. Yet the long-term health of the Masters community will depend on finding ways to make participation more accessible for younger adults – whether through regional events, flexible formats, or targeted outreach.
For now, the story is one of endurance. The Masters fleet is older than it was 25 years ago, but it is also thriving, competitive, and deeply committed. The sailors on the line today represent a generation that has stayed with the sport, adapted with it, and helped define what Masters sailing looks like in the United States.
2026 Viper Winter Series #3
Sarasota Sailing Squadron hosted the third event of the Viper Winter Series, drawing a competitive fleet and offering a mix of moderate breeze on Saturday and light, unstable conditions on Sunday. I joined Nick and Tobias for the weekend, continuing my week of winter sailing in Florida.
Saturday
The team rigged and launched early, sailing through the narrow channel and across Sarasota Bay to the course. Wind in the mid‑teens required de‑powering upwind, and I sailed in my cool weather ILCA gear – hiking pants, spray top and spray pants – which proved appropriate for the conditions. My position was the middle of the boat, responsible for hiking upwind, flying the spinnaker downwind, and in the later races I trimmed the main to keep the boat balanced through the chop.
Race 1 started with a bit of chaos. Another boat boxed us out at the committee boat, stalled and bumped into us. We had to shove them past just to get going, already a few lengths behind the fleet. The first beat was all about figuring out the boat and the conditions, and while clear air was hard to come by, we managed to pick off one boat by the finish.
In Race 2, the setup was better, but the short starting line and limited space made timing difficult, and we again started behind the group. Boat speed improved noticeably, especially downwind as we worked on linking waves and maintaining pressure. We finished ahead of two boats.
Race 3 produced the strongest performance of the day. A clean start allowed us to hold position with the fleet up the first beat, rounding the top mark in the mid‑fleet range. Despite losing a couple of positions later, we finished 8th and showed clear progress.
For Race 4, Nick offered me the helm. Approaching the line, I arrived slightly early and could not shed speed in time, resulting in an over‑early call and a return to restart. Shortly after, as the breeze built, I attempted to hike and discovered too late that my foot was under the bungee rather than the strap. I went overboard, breaking the tiller extension in the process. With the extension damaged and proper trim no longer possible, we knew our day was over. While Nick and Tobias got the boat back under control, I climbed aboard a nearby RIB and transferred back onto the viper for the sail in.
Post‑race, we attended the debrief, secured a loaner tiller extension for Sunday, and wrapped up the day grilling dinner at our Airbnb and doing some film study of our sailing.
Sunday
With the boat already in the water, Sunday’s rigging was straightforward. The forecast called for light wind that would fade by midday, with a possible late sea breeze. After a brief postponement, the race committee started one race in marginal but sailable conditions.
A solid start and a few early ducks positioned us on the side of the course we wanted, and clear air helped us round the first mark in 5th. As the race continued, some of the faster boats advanced, and the patchy pressure created opportunities and losses across the fleet. We finished 8th.
As the final boats finished, the wind shut off entirely. With Tobias needing to catch a flight and a long drive ahead for me, we had already agreed that any postponement would end our day. We sailed in while the fleet remained on the water. A sea breeze eventually developed, allowing additional races later in the afternoon.
We de‑rigged the boat, packed up, and I began the return trip to Richmond.
Thanks to Nick and Tobias for the opportunity to join them for the weekend. It was a valuable chance to learn the Viper, and extend my winter sailing break.
NBD
First new bike in *decades* and going to be doing more exploring.
