Sail with world-class skippers

“All I ask is a tall ship and a star to steer her by” – so goes the John Masefield poem. But if you don’t know how to sail, you need something else, and that’s a skipper… Luckily, we work with some fantastic ones.

I’ve only ever worked on boats in the lowest chain of command: as deckhand, as crew, and – unfortunately for all involved – as a cook. Even in these lowly ranks you appreciate the incredible efforts of a good skipper.

On a small group holiday, a good guide can make the tour. On a sailing holiday, the importance of a group leader is tenfold, because on boats, captains are kings.

Historically, captains – skippers – have had absolute power, ‘the captain’s word is law’, but also absolute responsibility, to the extent that historically ‘the captain goes down with the ship’. Times have changed, but some aspects of sailing remain the same – the rigid hierarchical order of a crew keeps everyone safe. Yes, even on holiday. When the sailing trip can be as epic as sailing to St Helena, it makes sense.

“The skipper will determine whether you have an amazing time or a terrible time. More so than anything else,” says Andrew Cowen, co-founder of our specialist sailing partner Wavysail “I’ve been on a miserable, rainy sailing trip on the south coast of the UK in the winter with an incredible skipper and still had an amazing time.”

In 2023, Guy Waites, skipper for our partner Wavysail, completed the Golden Globe Race, becoming one of very few people who have singlehandedly sailed all the way around the world. The effort took him 287 days. “He did the Golden Globe Race and then two weeks later he was skippering our Croatia trip,” says Andrew. “That’s the kind of experience we offer – imagine six people going on the boat and Guy Waites is the skipper – he came on after nine months of being completely isolated. I kept telling him: ‘Guy, there will be other people on the boat – remember to talk to them!’”

“Safety first, safety second,” that was our skipper’s mantra when I used to work on board. But it’s not just about being safe, it’s about feeling safe and relaxed – especially if you’re on a holiday.

“It’s feeling secure in a situation that could be quite scary, because it can be very lonely out at sea.” Heather Deary is operations lead at Wavysail and a keen sailor. “If you feel that your boat is your haven and that the person who is your skipper on it is reliable, you’re able to go to sleep at night feeling safe, and that’s key.” Heather came to sailing later in life but has since sailed round the world with Wavy as her skipper.

Our more adventurous sailing holidays might involve expedition sailing, offshore sailing and heading to remote places where the ability to pick up supplies, or see a mechanic – are non-existent.

“We develop our skippers slowly,” says Marcin Sanetra from our partner Sail Arctic, whose expedition sailing holidays explore areas like Greenland’s Scoresby Sound, where the wilderness is absolute. “You can’t find special services for your yacht and so on, so it’s very important that skippers know the yacht from a technical point of view.” They train skippers to adjust to sailing in Arctic environments by having them work alongside more seasoned crew. “It’s a slow process, but we know how to do it.”

I’ve stood long night-time watches in the cold, but acoustic guitars, ghost stories, and, when all else fails, salacious confessions, have helped speed the 4am to 8am graveyard shift along.

It’s useful to have someone on board who can hold a tune or tell a story. “We had one trip that was quite storm bound,” says Heather. “Out of ten days’ sailing, they were stuck in port for five days.” They expected bad reviews from travellers. The opposite was true, thanks to the crew. “We had five-star feedback,” says Heather. The skipper organised an onboard Highland Games to entertain everyone whilst they were waiting. “We even had someone saying that this was the best sailing holiday they’d ever been on.”

Like any tour leader, skippers are the glue that holds a group together: the mood boosters and the cajolers. “They have such a great connection with and empathy for people,” says Andrew.

Skippers can also inspire others. I sailed with a fantastic female race crew and skipper for a few races in the Mediterranean, and it was personally very inspiring to see a woman in charge. “I’m very happy that we have some good female skippers,” says Andrew. “We’ve never consciously aimed for female crew,” says Andrew – their hiring policy is to employ the best skipper for the job – “But we have at least 50:50 split on our boats.”

Travellers don’t need any sailing experience to go on a sailing holiday, which is why they need good teachers to show them the ropes. “Wavy has that magic combination,” says Heather: “Experience, and the ability to share his knowledge. It is really easy to learn from him… you learn without knowing that you’re learning.”

“Our skipper was very careful about recycling everything possible and no waste,” said our traveller Ellen Craig, who went on our Greece sailing holiday for families. “The skipper is a passionate environmentalist and we had some interesting discussions over dinner,” said our traveller Margot-Veronique Robinson, who embarked on our sailing and conservation holiday.

It’s no coincidence that sailing and responsible travel go hand in hand: “Most skippers are ocean advocates,” says Andrew, and it means that their company – which is trying to drastically reduce the carbon footprint of its holidays by removing polluting fibreglass from the yacht construction process – attracts activists. “We are genuinely passionate about showing people this amazing space and this resonates with skippers.”

With limited space on board, our skippers are often polymaths. On our sailing holidays you might fish off the back of the boat as you sail along, go scuba diving, practise Yoga, or sailing in the Arctic Circle, put an anchor on the ice, walk up to the snow-clad hills and go ski touring.

Whilst some of our holidays have a dedicated ski guide or other professional guide for off-boat activities, others use the skills of our skippers, many of whom have other qualifications to their name. And, luckily for me, some are very good cooks, too.