Sailing, Stories, and Familiar Faces in Annapolis
Last week we made our annual pilgrimage to Annapolis for the Sailboat Show, a familiar rhythm each fall that always manages to offer something new. The docks were packed, the air had that early-October sharpness, and the city was alive with sailors from every corner of the world.
The weather was ideal on Thursday and Friday, with clear skies and a steady breeze, while the approaching nor’easter dropped only a few sprinkles on Saturday and held off its full force until Sunday. Crowds filled the show from the start, and by Saturday morning it was standing room only along the docks. Boats of every type and size were on display, from sailing dinghies to performance cruisers and an impressive mix of multihulls. With more than 500 exhibitors and a wide range of boats in the water, many making their world debut, Annapolis once again proved why it sits at the heart of American sailing.
New to this year’s Annapolis Sailboat Show, Refit My Ride brought real-world restoration to the docks. Led by Dawn Riley and the Oakcliff Sailing team, the live, multi-day demo transformed a well-used Farr 40 into a race-ready showpiece using gear donated by show exhibitors.
From new Harken hardware to a Nature’s Head composting toilet, attendees could watch upgrades unfold in real time and pick up ideas for their own projects. The effort highlighted craftsmanship, sustainability, and the satisfaction of giving older boats new life. For those of us who love admiring the newest designs but sail 50-year-old boats at home, this project was both inspiring and exciting to see.
We caught up with Ronnie Simpson, a well-known professional sailor in our community, whom we have interviewed several times for the Good Jibes podcast. As you might remember, Ronnie came to his previous boat Sparrow through a listener of the his first Good Jibes interview. Ronnie shared updates on his dismasting in the Global Solo Challenge, his new adventures, and his next campaign aboard Koloa Maoli for the 2027 GSC in partnership with US Patriot Sailing. Ronnie’s girlfriend Marisa joined the conversation, sharing that she’s recently bought a J/29 and started racing in Maine.
While we were chatting, a young sailor named Finn stopped by to tell Ronnie they had met on the docks back in 2022 when he was just 15. That brief encounter inspired him to buy a C&C 34, complete a 1500-mile solo trip along the East Coast, and earn his captain’s license. Now, just 18 years old, Finn is proof of how far one inspiring moment on the docks can carry someone. You can listen to Ronnie on the Good Jibes podcast here, here and here. Be on the lookout for another interview about his dismasting and next GSC campaign.
We finally met Good Jibes guest James Frederick in person, along with his girlfriend Victoria. James was stateside for about six weeks after leaving his boat Triteia in Malaysia. The break gave him time to connect with friends and the sailing community before he heads back to continue his circumnavigation.
We ran into Kurt Jerman and Guinevere King from West Coast Multihulls, who sold an Excess 14 at the show. The teams from Cruisers Academy and Sun Powered Yachts were nearby, and our friends at Hydrovane were so busy we barely managed a quick hello.
There was plenty of industry news making the rounds too. 59º North recently purchased the historic schooner Woodwind with plans to continue to run her out of Annapolis. Their Farr 65, Falken, is set to launch later this month from KKMI in Richmond.
And of course, there were many celebrations. SpinSheet magazine marked its 30th year of publishing, a milestone that speaks to how deeply woven they are into the Chesapeake sailing community.
Annapolis was full of new designs, old friends, and stories being written on the docks. Every year it seems to capture a little of where sailing has been and where it’s heading next.