Is this the most foolhardy family holiday? Flotilla sailing after just a day's training

W e were sitting on the sand, waves lapping our toes, the sun stretching a dancing trail towards us. “We’ll spend the whole day arguing,” I said. 

With its crescent of sand, yachts bobbing against the quayside and glassy waters, Mongonisi on the island of Paxos, in Greece, is idyllic. 

Our son Joe was squealing with delight, splashing in the waves with new friends. But my wife, Karen, and I were a little stressed. The next day we’d be sailing a 31ft yacht – alone – for the first time. 

This was what had sparked our interest about Sailing Holidays – a family-run company that has been offering flotilla tours around the Greek islands for more than four decades. 

Unlike some other British operators, it lets you sail the boat yourselves. As total novices. And that’s why we were arguing in one of the most beautiful spots in the world.

Joe was six. He loved the film of Swallows and Amazons. He’s a confident swimmer, too. Karen and I were after the perfect blend of family fun and adventure on the high seas. We could learn the ropes together, swim in sparkling bays and be rocked to sleep by the waves. 

We arrived at Plataria on the Greek mainland a little jaded after an early flight. The lead crew showed us around Vanessa, our Beneteau 311 yacht and home for the week. Calum, Emily, Snakey (no idea why) and Spanish (well, he was Spanish) seemed ridiculously young. But they were reassuringly well-organised. 

“Look, Dad, it has a drawbridge!” shouted Joe. He dived down the steps to explore and we followed. 

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There was a compact lounge and a galley. To the right, a mini-loo cubicle with hand-held shower; fore and aft, two very cosy cabins. Stowage was a multitude of cubby holes. 

Within moments of unpacking, I couldn’t find things. The afternoon was a blur of briefings. There’s a pump for everything: bilge, loo, shower, sink (don’t muddle them). Engine, lights, radio, navigation system. 

There were 11 yachts in our flotilla. Apart from one other couple, everyone seemed to have at least sailed a bit before. Some were old hands. 

It was a little daunting. I’d have been having palpitations, despite the great-value wine in the taverna at dinner, but we had a secret weapon: we had booked a crew member to sail the first few days with us. 

Next day dawned sunny and serene. So was Ailsa. With the University of Aberdeen’s ladies’ sailing team captain aboard, what could possibly go wrong? 

Joe fell for her immediately. She kitted him out with life-jacket and harness, showing him how to stay clipped on to the railings around the deck at all times. This meant we never really worried about safety. And it kept him nicely occupied, too. 

Once we had puttered into the bay, Ailsa quickly had us putting up sails – and we had our hands full. The yachts have self-furling sails: you pull in one rope and up it goes. But you need to pull the correct rope, hard. 

“Start with the ‘genoa’ sail at the front,” Ailsa explained. I got the rope the wrong way around the winder and the sail billowed. I cursed. Eventually it was up. Then, we turned the engine off and the magic happened. The boat came alive under our feet, making a low humming sound as the wind filled the sail. 

The deck tipped as we caught more of the breeze. “Wooah!” cried Joe with excitement. 

Over the next three days, Ailsa showed us the ropes. We learnt to tack, turning into the wind, hauling the genoa across as the breeze picked up. 

We got the mainsail up and hit six knots. Joe learnt to tie a reef knot. I got blisters and regretted the fact that I had overlooked the recommendation to bring gloves. 

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Sailing is quite intense teamwork, requiring concentration and communication: perfect for testing marital harmony. During all this, Joe sometimes got a bit forgotten. He wasn’t strong enough to pull the ropes, and I wondered if we should have waited until he was a little older. 

However, what he could do was hold the wheel. Standing on the bench that ran around the cockpit, he could steer all on his own. This was popular. 

Each evening we moored in pretty ports on Paxos. Manoeuvring with the engine into a tight space and dropping anchor at the right moment was challenging. 

There was a huge sense of sweaty achievement at finally coming to a bobbing standstill. 

We dined most evenings en masse at local tavernas serving simple Greek food and carafes of local plonk. We made friends. Joe had fun, kicking balls around and playing games with the lead crew, who never seemed to tire. 

Which brings us up to Mongonisi and that pivotal decision. Could we really sail without Ailsa? 

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We had to. Pride was at stake. The other novice couple had been sailing without help. (Though I should point out that they’d been rescued by the lead boat several times and not had the sails up much.) 

The next day, conditions were perfect, the wind just off the bow. Motoring out between other yachts was stressful, but once we were in open sea, Karen held the wheel and I hauled on the genoa. Joe kept a lookout for pirates. 

We were moving! The mainsail went up and, again, we felt that pleasing rush of adrenalin as Vanessa seemed to pause a moment, then leapt forward across the waves.

Once we were on our way, we hoisted a Jolly Roger, which Karen just happened to have brought. Now we were real pirates.

“Can I steer, Dad?” Joe asked. “Sure,” I replied. 

And there we were, all three of us, sailing our own yacht on the azure sea. 

Next time we just need to show Joe how to stay on course. 

The essentials

A seven-night Paxos flotilla holiday with Sailing Holidays (sailingholidays.com) starts from ￡495 per person based on four sharing a 31ft yacht, including flights from Gatwick to Preveza and transfers. Having a crew member on board costs ￡80 per day.