All at sea in Antigua, one of the last winter sun options for Britons

Ruaridh Nicoll
·10-min read
Ruaridh Nicoll learns to be a ‘competent crew’ on a liveaboard sailing break in breezy Antigua - getty
Ruaridh Nicoll learns to be a ‘competent crew’ on a liveaboard sailing break in breezy Antigua - getty

With a steady breeze carrying us onwards, the Blue Moon, a 43ft Grand Soleil yacht, slices the western seas off Antigua. At the helm is Edoardo “Edo” Monti. He’s a trainee day skipper and he’s ready to gybe. 

“So,” he says to his novice crew. “We’ll pass the wind with our stern.”

I start laughing, and soon I am joined by the others. Edo attempts to maintain the dignity of his office by looking put out. I can see I’m going to be coiling ropes – sorry, sheets – for some time.

In truth, being ordered about by a 27-year-old has been rather good for me. I’m 50, and while I don’t like being told, it’s helping an old dog learn a new trick. And it’s a trick I want to master. I live in Havana, Cuba, and have improbable visions of sallying forth to explore the Antilles, without adding further to the carbon in the atmosphere.

While Edo is the skipper, we are under the tutelage of Thalita Zur Werra, a 45-year-old Swiss instructor for Second Star Sailing, named after Peter Pan’s instructions on finding Neverland: “Second star to the right and straight on” – although Thalita says: “People keep asking why we are not First Star Sailing.”

There are worse places to try you hand at sailing - getty
There are worse places to try you hand at sailing - getty

Last year the school launched a winter operation based in Antigua’s Jolly Harbour after five successful summers operating out of Pisa, Italy. They offer all the Royal Yachting Association (RYA) qualifications, from the various Yachtmasters down to an entry-level, five-day “Competent Crew” course. That is the one I am doing, in the days before Covid security was even a term. 

We gybe. The bow turns through the shimmering Caribbean Sea and Antigua’s rough flanks move to starboard. I tighten the jib too much for a broad reach. So far, so incompetent.

Second Star’s base is a nondescript house on a harbourside street which the taxi driver struggles to find. All the houses back on to the quayside, although you wouldn’t know but for the occasional glimpse of masts through the gaps in the terraces. The residents include retirees, fishermen and waterborne tour guides.

The Caribbean islands you can visit without a quarantine
The Caribbean islands you can visit without a quarantine

The door is opened by Second Star’s Italian-American owner, Lyssandra Barbieri, all tanned sharp angles under an explosion of grey-black hair. On the veranda behind are her yachtmaster students – Italian, Swiss and an Albanian – all startlingly fit. One, Giorgio Benolli, is so absurdly buff and hirsute that he is the spit of a young Fabio, the 1990s model and actor.

These are the pros, heading for a career on the water. They crewed the school’s two yachts, Blue Moon and the slightly smaller Hatha Maris, across the Atlantic for the season. These people suit their role as young sea-dogs, washing themselves under the hose on the pier, and living on the boats. Which, it turns out, is what I will be doing. 

Lyssandra Barbieri
Lyssandra Barbieri

Thalita shows me on to Hatha Maris, which roughly means, “balance of the seas”. It is a Dufuor 40, and was previously used by Neapolitan racers who had called it Hathamurri, slang for “you should die”. Lyssandra decided to risk the sea gods’ ire by changing the name.

The boat is sparkling clean, but bijou. I am taken to the stern cabin which I am to share with Edo. Since I was a boy, I have always had a fear of living on board. Frozen childhood days on the Firth of Clyde being shouted at by a friend’s father convinced me that boats are, in essence, floating jails. 

There are positive signs that this operation will be different. Thalita wears a T-shirt that reads “Women at the helm” (she captained an all-women crew across the Atlantic on Hatha Maris). “We’re not women only, certainly not,” she says, “but in Italy women are often confined to the cabin and cooking. It can be quite macho. That doesn’t happen here.” 

Learning the ropes
Learning the ropes

Soon, I am learning how to throw a rope. The technique is to hold coils in each hand and a loop between, cross one’s arms, and then fling your arms outwards to full stretch. “Like Pavarotti,” cries Thalita. My lines splash uselessly into the water. “Pavarotti,” says Lyssandra. “Not Bocelli.”

We motor out of the harbour. Offshore, a steady 16-knot westerly is blowing, which is almost a fact of life in the Leeward Islands, offering some of the best sailing in the world. Thalita teaches us to hoist the mainsail, with me clambering around the mast, rolling out above the waves.

Edo is downstairs plotting a route to English Harbour, where Nelson had his headquarters in 1784, while Thalita keeps her eye on the GPS. It’s January and, I’m told, raining in the UK. I look at the hotels clinging to cliffs above golden beaches. The skyline tops out at Boggy Peak, renamed Mount Obama in 2009, Antigua’s highest point. It’s where slaves used to hide during the horror era of the plantations.

I take the helm, and the boat slows. “It’s impossible to sail into the wind,” says Thalita, her tone drier than anything else on-board. I settle into a close haul, and swiftly fall in love with Hatha Maris as she runs at six knots across a “moderate” sea that swings the bow like a dodgem as we crest the peaks. 

Whitewater runs along the gunnels as we heel. I’m in awe of the fourth member of our crew, Helene Gyselinck. She has escaped the cold of Toronto to spend the winter on a friend’s boat, but he refuses to take her out until she knows her knots. So here she is, reefing and hauling, as game a 67-year-old as ever battened down a hatch.

We tack back and forth up the coast. Both Thalita and I want to make English Harbour in time to see a rowing boat taking part in the Talisker Atlantic Challenge arrive. But it’s hard yards, and we’re still short when the sirens sound across the sea.

"I live in Havana, Cuba, and have improbable visions of sallying forth to explore the Antilles, without adding further to the carbon in the atmosphere"
"I live in Havana, Cuba, and have improbable visions of sallying forth to explore the Antilles, without adding further to the carbon in the atmosphere"

We turn instead for Falmouth, just across an isthmus from English Harbour, and motor into the kingdom of the superyachts. We watch their crews scurrying over the shimmering flanks of these vast beasts, tanned kids who are spending their winter washing the toys of the super-rich. 

I ask Thalita which of the superyachts she likes best. Perhaps David ­Reuben’s sparkling Siren? Or Bill Joy’s slick Ethereal? How about Skat, done up to look like a battleship by Charles Simonyi, inventor of Microsoft Office? 

She frowns and finally points towards an elegant sliver of wood with three masts, the sort of vessel that probably belongs to a designer from Apple.

I bathe in the less-than-superyachtie showers onshore, muttering about the broken faucet and dirt. (When I finally complete my course, I drop by Jumby Bay, a famously expensive resort, to practise my new skills on its fleet of Laser dinghies. I ask whether my room has a shower. “It has three,” they say, and I nearly cry.) For the moment though, I am happy just to have water. 

We drink a couple of beers in a pier-side bar, and that night I fall into as deep a sleep as I can remember.

Over the following days, the learning comes at me like squalls. We take turns to sail Hatha Maris through 360 degrees in each of the roles – responsible for the helm, each jib, the mainsail. Fenders go out and come in, men (decoys, fortunately, although Thalita does eye me) get thrown overboard and are retrieved. We take turns to cook, including a mahimahi I buy from a fisherman.

"Over the following days, the learning comes at me like squalls."
"Over the following days, the learning comes at me like squalls."

“Food is important on a boat,” says Thalita, who has crossed the Atlantic four times. “If everyone is well fed, all is well.” 

We drop into coves so Thalita can see them for the first time. I try to fish, but lose the lure overboard. Often we make a mess of things and Thalita looks with shame at passing vessels. At one point the mainsail sheet runs free, whipping Helene’s knee. “Ouch,” she cries. “That was like a carpet burn,” she grins.

Anchored off a fancy hotel at Hermitage Bay, we dine on deck as the ­retreating sun immolates the horizon. One of the superyachts anchors nearby, illuminating the sea around about with underwater lights and releasing a squadron of jetskis. 

I gape a little. It never occurred to me that these vast boats do exactly what little boats do, pull into pretty bays and anchor up. I’d always assumed there was some secret Jurassic Park-style island out there where they all go to hang out.

That night Edo wakes me by getting up, saying he can’t sleep. “I thought I’d check my bearings.” He goes on deck and then returns. “Yes, we’re still in the same place.” He then starts snoring. I will never get used to living cheek by jowl with people I can’t pinch.

On our final day, we switch boats and head out with both Thalita and Lyssandra on Blue Moon. Having grown up in Tuscany, Lyssandra went to work in Silicon Valley, earning the resources in start-ups to “turn my passion into a job”. Her father had raced yachts and she had often stowed away. 

“I realised the sailing schools weren’t run the way I thought they should be, that they aree very male-dominated,” she explains. “What we really want to do is make sure that anyone who goes sailing, whatever their gender, is able to perform at the level they expect to perform. We’re trying to take out the intimidation some women feel.”

She has come aboard today because her yachtmaster students are doing their exams on Hatha Maris. She is clearly suffering as her ducklings set out on to the open sea unprotected. 

After she has checked our competency for the RYA certificate, she asks if she and Thalita can run through their racing paces. We watch in awe as the boat comes alive in their hands.

As the day ends, we head back to Jolly Harbour. Other yachts are coming in, Lyssandra muttering as she watches the men at the helm, the women putting out the fenders. I wait at the bow, ready to Pavarotti my lines as we come alongside the pontoon, my widening arms an expression of competency. 

How to do it

Ruaridh Nicoll was a guest of Second Star Sailing (secondstarsailing.com). Its five-day, liveaboard RYA Competent Crew course costs from £790.

Seven days at Jumby Bay Island cost from £5,585pp, with flights, through Elegant Resorts (elegantresorts.co.uk). 

British Airways (ba.com) flies daily to Antigua.

Travel to Antigua is currently allowed without the need to quarantine on returning to the UK, but entry requires a negative Covid-19 test. For the latest travel advice, see gov.uk/guidance/coronavirus-covid-19-travel-corridors.