Wrapping Up the 2025 Annapolis Sailboat Show: Smooth Sailing Amid Chesapeake Charm
by CeCe Cogar
As the sails come down on the 2025 Annapolis Sailboat Show, which wrapped on October 12 after four days of nautical nirvana at City Dock, the event once again proved why it's dubbed the world's largest in-water sailing spectacle—over 50 years strong and still not showing its age. With the Chesapeake Bay as its backdrop, this year's edition drew enthusiasts from afar, blending cutting-edge boats, hands-on demos, and that unmistakable Annapolis energy where every conversation seems to end with "fair winds."
Attendance: A Steady Breeze of Visitors Early indicators suggest robust turnout, building on the momentum from the preceding Annapolis Powerboat Show (October 2–5), which pulled in over 30,000 attendees, its strongest since 2021. The Sailboat Show, historically a crowd-pleaser in its own right, likely mirrored this surge, especially with the expanded City Dock layout courtesy of Annapolis's redevelopment pause, allowing more space for exhibits and elbow room.
Solo Odyssey: Ronnie Simpson's Defiant Dance with the Global Solo Challenge
In the vast, unforgiving expanse of the world's oceans, where the horizon mocks the limits of human endurance, a new breed of sailor dares to chase the impossible. The Global Solo Challenge (GSC) isn't just a race—it's a gauntlet thrown down by the sea itself, demanding solo voyagers to circumnavigate the globe non-stop, unassisted, threading the needle through the infamous Three Great Capes: Good Hope, Leeuwin, and the treacherous Horn. Launched in 2023, this audacious event levels the playing field for amateur dreamers and seasoned salt alike, pitting modest 32-foot sloops against sleek 40-foot racers through staggered starts that equalize the odds. It's budget-friendly, eco-conscious, and brutally honest—no prize money, just the raw glory of survival and the whisper of wind as your only companion.
Ronnie Simpson at the Annapolis Sailboat Show 2025
Amid this symphony of saltwater and solitude stands Ronnie Simpson, a 40-year-old force of nature from the rugged shores of Portland, Maine. A Purple Heart-decorated US Marine Corps veteran whose life was forged in the fires of Iraq, Simpson found redemption not in therapy rooms, but on the heaving deck of a sailboat. His story is one of resurrection: from the scars of war to the thrill of single-handed global conquest. In the inaugural GSC, Simpson pushed his Open 50 Shipyard Brewing to the brink, only to be humbled by a catastrophic dismasting south of Cape Horn. Undeterred, he's now charting a comeback aboard a nimble Class 40, eyes fixed on the 2027 edition. This is Ronnie Simpson's saga—a tale of grit, grace under gale, and the unquenchable pull of the sea.
The Genesis of Grit: Unveiling the Global Solo Challenge
Picture this: Twenty intrepid souls, each a universe unto themselves, scatter from Spain's sunny docks in late 2023, bound for a 24,000-nautical-mile odyssey that could span five months or shatter souls in weeks. The GSC, brainchild of Italian innovator Marco Nannini, flips the script on elite ocean racing. No corporate juggernauts here—just everyday adventurers in boats as humble as a family's vacation cruiser, racing against behemoths that could swallow them whole. Smaller vessels get a head start, turning potential mismatches into a nail-biting ballet of strategy and stamina.
The route? A merciless loop: from A Coruña, Spain, southward past Africa's fiery coasts, skirting the ice-choked fringes of Antarctica via the capes, then northward through the Pacific's endless blue yawn, and home via the Atlantic's trade winds. Storms that could flay paint from steel, rogue waves taller than houses, and the psychological vise of isolation test every fiber. In the 2023-24 edition, French veteran Philippe Delamare clinched victory after 147 days, 3 hours, and 56 minutes—a testament to the event's ferocity, where over half the fleet retired amid mechanical mayhem and Mother Nature's wrath. Yet, for those who endure, the GSC offers something priceless: proof that the human spirit, lashed to a tiller, can outfox the abyss.
Koloa Maoli—Class 40 hull #15
The GSC reminds us: these waters aren't conquered; they're stewards we must honor. With the next chapter slated for 2027-28, whispers of expanded fleets and tech tweaks hint at an even bolder horizon. But no narrative captures the GSC's soul quite like Ronnie Simpson's—a man who didn't just race the waves; he wrestled his demons upon them.
Rebirth on the Roiling Horizon: Simpson's Charge Toward 2027
Simpson's journey from the ashes of his dismasting to the brink of another GSC attempt is a saga of relentless resolve. After the heartbreak of 2023, where a snapped mast forced him into a harrowing rescue, Simpson's spirit remained unbroken. "I learned more about myself in those dark hours than I ever did in the Marines," he reflects. The decision to switch to a Class 40 wasn't just strategic; it was symbolic—a nod to agility and resilience over sheer size. His new vessel, a sleek, carbon-fiber marvel, is being meticulously prepped for the next GSC, with every line and sail tuned to perfection.
Fast-forward to October 2025: Portland's autumn fog cloaks Simpson's latest lair, a humming yard where Koloa Maoli—Class 40 hull #15, a 2006 Owen Clarke stunner—takes shape. Acquired in February from GSC 2023 sixth-placer David Linger, this 40-footer is Simpson's phoenix: lighter, nimbler, built for the capes' chaos. Her carbon bones and canting keel promise velocity without the Open 50's bulk.
2025 Annapolis Sailboat Show Closes with Strong Attendance, Industry Momentum
The 2025 Annapolis Sailboat Show concluded Sunday following four days of impressive crowds, vibrant programming, and sustained industry momentum. Held Oct. 9–12 at Annapolis City Dock, the internationally recognized event once again served as a dynamic meeting ground for sailing enthusiasts, marine professionals, and new boaters.
Despite a forecast that tempered Sunday attendance and delivered challenging winds, overall turnout remained strong. Exhibitors across the docks reported increased interest and healthy sales, signaling continued growth and engagement in the sailing sector.
Annapolis Boat Shows extends its sincere appreciation to the City of Annapolis for pausing the City Dock construction project during show days, ensuring an optimal experience for attendees and exhibitors alike.
Boat Show Brew: The Pilsner That's All Hands on Deck for the Chesapeake
The Annapolis Sailboat Show pulsed with life starting on October 9, 2025. The newly redeveloped City Dock brimming with over 400 boats. Amid the gleaming hulls and salty Chesapeake air, a tap tent poured Boat Show Brew, a crisp pilsner crafted by Pherm Brewing as the official beer of the 2025 Annapolis Boat Shows. Its light, refreshing bite drew a crowd of sailors and visitors, all savoring the taste of the bay.
Boat Show Brew, the official beer of the 2025 Annapolis Boat Shows
The brew's debut at the show was more than just a refreshment; it was a celebration of Annapolis's rich maritime heritage. Visitors clinked glasses, shared stories of the sea, and toasted to new adventures on the water. Boat Show Brew, with its perfect balance of malt and hops, quickly became the drink of choice for those looking to unwind after a day of exploring the latest in boating technology and design.
This beer that's brewed for the boat show is more than just a drink; it's a way to support the community. Proceeds support the Eastport Yacht Club Foundation’s marine and maritime programs, like scholarships and Chesapeake stewardship.
Interesting Facts: From Hybrid Hulls to Historic Vibes
Fun tidbit: The show spotlighted eco-innovations like the Birdyfish hydrofoiling dinghy and hybrid catamarans, nodding to sustainable sailing's rise. In a rare Annapolis twist, the Kaye family sold their iconic 74-foot schooners Woodwind I and II to 59º North Sailing just before the show, marking a generational shift in local maritime lore. And for trivia buffs, this year's emphasis on performance vessels echoes the spring show's focus, where competitive sailing stole the spotlight.
All in all, the 2025 Annapolis Sailboat Show sailed off into the sunset as a win for the Chesapeake community—proving that in sailing, as in life, the best highlights come with a little wind in your sails and a brew in hand. If you're already plotting next year's visit, mark your calendars: the tradition continues to evolve, one premiere at a time.
Boat Sales and Buzz: What the Crowd's Saying
Sales data remains under wraps for now—organizers might be too busy counting commissions—but the vibe points to brisk business, fueled by the show's reputation for deal-making amid the docks. Exhibitors like Catamaran Gurus, Xquisite Yachts, and Catalina dealers reported buzzing activity, with posts highlighting US debuts and sustainable hybrids drawing crowds. On X, attendees raved: "Beautiful weather and good crowds made for an amazing first day," with one vendor noting the docks were "in full swing." Post-show reflections echoed the sentiment—sailors gathered from around the world, stocking up on "industry knowledge" and dreaming of their next voyage. Even the nor'easter added character, as one poster shared: "Riding out the noreaster... still a calmer ride than at dock in Dunkirk NY." YouTube tours amplified the excitement, showcasing tons of new boats and gear.
