An On-the-Water Report from One of the Caribbean’s Most Beautiful Sailing Events
By Kelly Merton
For over three decades, the mere phrase “Antigua Classic Yacht Regatta” has summoned dreamy visions of glass-like varnish, towering wooden masts, crisp white sails, and elegantly dressed sailors participating in the ultimate “gentlemen’s race.”
What’s far less expected- but arguably far more fun!- is the deeply-tanned, sunglass-free woman donning a well-worn woven straw hat and a shockingly vibrant purple tropical shirt who greets me as I walk the docks of the famed Nelson’s Dockyard in Antigua’s English Harbour on Day 2 of the 36th Annual Antigua Classic Yacht Regatta in late April 2025.
A faintly German accent accompanies her bright smile the first time I hear Angie Wolf, owner/skipper of S/V Cherub, greet me and welcome me aboard her lovingly restored 42’ gaff-rigged Venus Ketch called Cherub.
Once aboard, a chorus of international accents accompany the friendly faces as the all-female crew aboard introduce themselves in rapid-fire succession. First it’s Meg, originally from New Zealand, but now calling the slopes of British Columbia’s snow-cat country home. Next is the Canadian mother-daughter team of Krissie and Dairan, American expat turned full-time Caribbean cruiser Vanita, and former English nurse Janet (whom I’ll come to learn is one spirited sea-shanty singer!). While all of these ladies are experienced sailors in their own right, the Classics regatta marks the first time many in the crew has not only sailed together, but also sailed aboard a gaff-rig.
Thankfully, however, not everyone aboard are gaff-rig newbies. Two of Angie’s friends, Bronwen and Coralie, regularly sail with Angie in the Grenadines and bring to the regatta crew some much-needed gaff-rig experience. In the days preceding the regatta, they completed the 3 day, 160-nautical mile (~500 km) delivery sail from the tiny island of Carriacou to Antigua.
With crew introductions in the book, dock lines are cast off, Cherub emerges from her Med-moored slip. Despite shaking off the lingering effects of a few boat drinks imbibed the previous evening, the entirety of the crew are in excellent spirits! Day one served up a mix of big air, lumpy seas, and generally “sporty” conditions, so their collective confidence soared in securing a class second in Day 1’s race (and only the second time this crew sailed together!). As sails are hoisted to a bellowed chant of “one..two.. hoist,” fragmented choruses of popular Jimmy Buffet and Zac Brown Band songs excitedly spill from the lips of Jan, Dairan, and Krissie. It’s time for another day of racing and everyone is ready!
As Cherub and her fellow competitors begin emerging from the protection of English Harbour into the Caribbean Sea, the most unexpected visitor suddenly appears in the already-at-capacity cockpit: a cat! I quickly came to learn this feline friend, affectionately known as “Woozle,” was a package deal with the boat when Angie came into Cherub’s possession three years prior. Woozle- like Cherub herself- was beloved by the boat’s former owner (and Venus fleet designer), Paul Erling Johnson. If his name sounds familiar, you’re either a niche-boat design enthusiast or quit ethe cinephile: because in addition to being the subject of a number of articles (including one the Oct 2020 issue of Caribbean Compass), Paul was the subject of an award winning 2021 documentary about his life and career, in the aptly named The Sailor.
As the clock inches towards the 10a start time and regatta participants make their way north from English Harbour, it’s immediately evident it’s a “champagne sailing” kind of day featuring bright skies, 12-15 knot sustained breezes, and gently rolling seas.
When the fleet approaches the starting area, we’re met with what is likely one of the most gorgeous yachts ever to serve as a regatta Committee Boat. Marie is a 1930-vintage 136’ motor yacht who’s explored the world many a time before being meticulously restored. With her dark, glossy hull, crisp canvas, and glistening varnish, one envisions refined tea parties of high society yesteryear, not multi-boat tussles for the favored end of a regatta starting line!
After a bit of tacking around in the starting area, a gun sounds, and the Day 2’s race is officially underway! Despite being later to the line that one might hope, Cherub finds clear air and settles into the first leg the 20 nautical mile “Butterfly” course, one of the longest in the regatta. After crossing the starting line, competitors first head 4 miles west to a mark known as “Cupples”. Cupples is the first mark in all of the pre-announced courses, and is named in honor of the regatta’s beloved, late, and long-time Race Chair, Ms. Clare Cupples.
As Cherub and the fleet approach the first mark of the day, a bit of traditional racing drama ensues. Because Angie knows gaff-rigged boats don’t point very high, her plan is to hold her course while intentionally overshooting the mark, then head out further out to sea in an attempt to get closer to the Cape Shirley turning mark layline. But just to starboard, the tactician of Sahret of Tyre, a 32 meter (106’) 1933 Bermudian Ketch, is calling for us to tack. He’s claiming that they’re the leeward boat, so he tries to push us up and over early. And while it’s true they are to lee of us, we’re within the three-boat-length circle of the turning mark, so this typical rule is superseded by his requirement to give us room at the mark (Rule 18 in the Racing Rules of Sailing (RRS)), the rules that govern the regatta, per the Sailing Instructions.
But despite much boat-to-boat shouting and Sahret’s attempts to intimidate us out of our fairly-held position, Angie knows her rights and holds her course. On Angie’s call, Cherub successfully tacks away and heads for Cape Shirley. And while this sort of energetic banter at the mark is par-for-the-course for an experienced racer, for this crew of cruisers, the rounding proves to be an adrenaline-inducing experience! On the beat the next mark, the crew busies itself with a passionate debriefing and accolades for Angie’s composure, knowledge, and skill!
As Cherub rounds the mark at Cape Shirley, the experience of tactician Bronwen is on full display. While donning an eclectic mix of brightly colored tropical and bold animal prints, she confidently instructs the crew to set the sails on opposite sides of the masts, sending Cherub on a “wing-on-wing” downwind run. While a dead-down(wind) course may be considered a bit risky by some (due to the potential for an accidental broach), but Bronnwen is no stranger to these waters or conditions, as she successfully skippered her 1966 34’ Morgan, called Sea Swan, to a class-second in the 2023 Antigua Classics.
While Angie ever-so-slightly coaxes the massive wooden tiller to catch the gentle rolling waves hitting our stern, Bronwen’s soft, sing-song South African accent can be scarcely be heard beyond the the cockpit as she heaps accolades on Angie for her excellent driving as Angie remains deeply connected with the boat and water for the duration of the seemingly endless leg.
But finally, the downwind leg is complete and we’re back at the entrance to Falmouth Harbour. However, despite having already logged two hours of race time, we’re only at the halfway point, as Cherub still has to sail the other “wing” of the Butterfly Course! But time has been good to the crew, and everyone has clearly settled into their jobs. Although the cockpit is a fairly cozy space, Megs and Jan have found operational cadence with Angie and Bronwen at the back of the boat. The life-long bond of Krissie and Darian is evident as they work seamlessly to keep the sails aloft trimmed to perfection, while Vanita, positioned midship, remains focused on the flying jib, acting as “eyes” for the trim team in the cockpit. And on the bow, it’s the enigmatic Coralie who’s the star of the show. Her bare feet adeptly propel her to the end of the cantilevered wooden bowsprit as she makes minor tweaks to the sails. When I ask her about her sailing experience, in a thick French accent she coyly replies that she only began sailing when she first arrived on Carriacou six years prior. This is hard to believe, as she’s clearly a natural!
After a near-miss of a passing squall, the ladies enjoy a calm, blissfully shaded final leg. The calm, following seas gently roll the boat forward and a trance-like state takes hold of Cherub and it’s in this leg that much of the crew simultaneously recognize both our shared and individual good fortunes. We recognize the good fortune to have the health and time and connections to simply be present- and in each other’s presence. While the crew ranges in age from their 20s to 70s-ish, the shared recognition of all of the individual moments that led us to be aboard a beautifully restored – and perpetually loved- unique old boat on a Top-10 day, with a group of confident, empowered, and downright fun women wasn’t for a moment lost on anyone, and I can personally day the day was the pleasure of a lifetime.
Krissie’s voice rings out as she hails the Committee Boat on the VHF, announcing our imminent crossing of the finish line. After over 4 hours of racing, Cherub was done! And with the confirmation of completion from the Race Committee, the formerly all (okay, mostly!) business crew shifted into party mode! In what felt like seconds, the ever-bubbly Darian had not only stealthily popped below, but was already back in the companionway distributing ice-cold cans of Carib lager. Megs materializes from the galley asking if I, too, wanted Carib, but I declined, murmuring I’m not much of a beer drinker. That assertion must have been music to Bronwen’s ears, as she kindly, but excitedly, suggested I try one of the rum cocktails Megs whipped up the prior day. And who was I to say no after such a special day?!
Rum-drink in hand, I take a seat in the cockpit next to Angie as Bronwen helms us home. Without prompting, Angie begins sharing details about her dear friend, former Cherub owner and Venus boats designer, Paul Erling Johnson. With a fond, but longing, smile on her face, she spoke about his passion for designing beautiful boats, sailing the world, and his love of women.
To understand Angie’s love for the Venus, one must understand a bit of the boat’s back story. The 42-foot Cherub is a Venus 6, so named because it was the 6th boat designed by Johnson back in 1976 in Bermuda. Though Johnson originally designed this boat for a client, Cherub “boomeranged” back to him after his boat, a Venus 38, was shipwrecked off the coast of Martinique in her maiden voyage. After Paul was heroically rescued by helicopter, Cherub’s owner gave Paul this boat back to him, and for over 40 years, he loved Cherub as much as Angie has for the past four years.
Prior to his passing in 2021, Paul was lucky enough to have Angie as his increasingly formalized caretaker in his final years. When Paul’s health declined and Angie progressed from his on-water food delivery provider to vodka rationer to medical aide, he came to rely on her- a former geriatric nurse- to serve as his constant companion. As friend and marine photographer Jan Hein recalls “her company was gold to Paul,” so it makes sense that he chose to bequeath to Angie his beloved Cherub.
From 2021-2024, Angie threw herself into restoring Cherub to her original splendor. Three years of painstaking work had just been completed in spring 2024 when the unthinkable happened: on July 1, 2024 a powerful, early season Category 4 Hurricane, Beryl, slammed into the previously “safe” Southern Grenadines. Islands in the chain, including Carriacou, endured hours of sustained winds of over 150 miles. Homes and businesses alike had roofs ripped off, trees were uprooted, and Cherub– along with countless other vessels- were battered and tossed like toys deep into the mangroves of Tyrell Bay. In the immediate aftermath of the storm, friends recall Angie being the hero and glue of the island. Jan Hein recollects hearing from locals about all Angie did to help the dozens and dozens of boats trashed in Beryl. “Some folks are takers,” shares Jan, “and a few, like Angie, are givers, through and through”
And so the success of Cherub and her all-women crew at the 2025 Antigua Classic Yacht Regatta isn’t lost on Angie Wolf. This “little boat that could” finished the regatta in a very respectable second place in her class (and a corrected time of less than a minute over the 3rd place finisher in a 4-hour race!), but for Angie, the real victory was simply showing up.
What’s next for Angie and Cherub isn’t entirely clear. She knows she wants to empower women and enjoy life, but she plans to see where the wind takes her. Like so many of her friends, I know I’ll always look to the horizon, seeing if I can spot her faded red sails in the sunset.
