Could you survive a sailing trip?

Thinking about trying a sailing trip but not sure what to expect? Here’s how to get started, from gauging the costs, to knowing the risks, to deciding where to go, to – eventually – becoming a master of the seas.

7 mins

Why sail?

For the wind in your hair and the sun on your back. Dee Caffari – the first yachtswoman to sail single-handed around the world in both directions – suggests it’s the power of nature that makes a sailing adventure so attractive: “You feel insignificant against a vast ocean. Mountainous seas and gale-force winds are far stronger than you can ever imagine.&rdquo

It’s also a way to see parts of the world and wildlife your land-lubbing counterparts won’t, adds Nik Brbora. He completed the Clipper Round The World Yacht Race in 2012 and during his circumnavigation he was lucky enough to see pods of whales, glowing bioluminescence in the waves and outstanding crimson sunsets.

As romantic as it sounds, it obviously can get rough so, first, make sure you actually enjoy life on a boat. The reality of a floating existence can mean being confined in a small space, possibly getting seasick, being away from certain creature comforts.

Old sailing ship in tropical landscape (

Old sailing ship in tropical landscape (

Is it for you?

Test out life on the water by committing to a day or weekend sailing trip locally first. If you enjoyed that, then take the plunge and sign up for an easy-going week’s cruise abroad – such as a Turkish gulet (wooden sailing yacht). Like that and you could graduate to a skippered yacht or a flotilla trip. On the former, a qualified sailor mans the helm and you can help out as much as you like. On flotilla trips, a small group of yachts sail a planned route together, following a lead boat manned by an experienced skipper and crew.

For introductory sailing trips Bruce Jacobs, of adventure sailing company Rubicon 3, recommends destinations such as Croatia, Greece or Italy. The need for qualifications before embarking on a flotilla trip varies between countries and areas – so do check.

Learning to sail (

Learning to sail (

Learn some skills

To get the most out of a sailing trip and feel involved in the experience you should, quite literally, learn the ropes. Novices should begin at the Royal Yachting Association ( or, for our US readers, the American Sailing Association (, with numerous schools countrywide. Nik recommends RYA Competent Crew and Day Skipper courses; both take about five days to complete. He adds that sailing in the UK offers the best practise: “With its tough weather and tides, the saying is: ‘if you can sail in the English Channel or North Sea you can sail anywhere’.”

However, Dee argues that first experiences should be positive rather than rough: “The wind should be kind and the temperatures warm.” Gibraltar and Australia’s tropical Whitsunday Islands are good places to start, with safe and reputable sailing schools. To actually take the helm and skipper a boat, though not a legal requirement, it’s worth gaining the RYA Yachtmaster certificate. It’s a big commitment though – before the exam you must have completed at least 96 uninterrupted hours at sea, traversed 200 miles and helped select the route as a skipper or mate of watch.

Another way to gain instant experience is to do as Nik did and go from amateur to globe circumnavigator by entering the year-long Clipper race, an event that gives novice crew members the chance to sail around the world for around £30,000 – or join just one leg (£4,000). Learning the techniques of sailing is just one part of becoming a bona fide sailor. If you’re dreaming of taking your own epic voyage around the world you’ll need to learn a lot, from first aid to using a radio, meteorology, boat maintenance, right down to fixing a diesel engine.

Crew only sign (

Crew only sign (

Joining a crew

Fortunately, you don’t need a yacht of your own to sail the world – you can jump aboard someone else’s. You may be able to secure a free berth on a sailing boat (including bunk, board and transport) in exchange for labour. You’ll be at an advantage if you have some sailing experience or qualification. If you can cook or clean, you could get an entry-level position as a deckhand, steward or chef.

Fruitful places to find a free ride include Caribbean ports, the Azores and Southampton in the UK. Crewseekers is a good place to start; also yachting magazines or local sailing clubs.

Aerial view of yacht near coral reef (

Aerial view of yacht near coral reef (

What to expect

Sailing expeditions vary greatly, depending on whether you’re planning to cross the English Channel, traverse an ocean or sail around the globe. You’ll spend a good proportion of time prepping the boat and checking those vital weather charts. All expeditions require a lot of planning, Bruce says: “Once you are far from shore, it’s too late to think about missing items or find the vessel is not fit for purpose.”

Where to sail?

Consider the time of year and likely winds, currents and storms. “We often leave the northern hemisphere in the early winter so we can sail in the Southern Ocean during its summer,” says Dee. “Other concerns are the Caribbean hurricane season and ice in the extreme north or south.” If you just want to explore a nice spot for a few weeks, there are plenty of options.

The 32 islands of the Grenadines are a good Caribbean choice – the trade winds are reliable and the waters sheltered. Cape Town is a good year-round sailing destination; sailing courses here tend to be good value, and you might spot penguins, dolphins and whales from the deck.

Be aware that some territories are riskier than others: the Malacca Straits, the Bering Sea, the Bermuda Triangle, the North Atlantic, Cape Horn – to name a few. But as Dee says: “If it were easy, everyone would be doing it!”

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15 reasons why sailing around the world may not be for you – Aimee Nance

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Main image: Sunrise on a yacht (

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