How To Prepare For Sailing Around The World

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Since leaving the UK on our sailing adventure, we met many wonderful cruisers. Some of them sail full-time, some do it only a few months a year; but most of them have prepared for cruising for years before setting off. It made us feel a little guilty, maybe even reckless – we had the idea of sailing away in 2016 and set off within a year of that lightbulb moment. We were impatient, daring, and didn’t care for luxuries, so we just worked as hard as we could to buy a tiny sailboat and untied the lines, fast. Luck was on our side, so it all worked out for the best. But to tell you the truth, we could have been a little more cautious and prepared.

We wouldn’t recommend preparing for cruising (especially if you want to sail around the world) the way we did, unless you’re willing to keep things super simple, like us. Here’s a list of practical things you can do to prep for the live aboard life and make sure you’re making the right decision, as well as feel confident when you set off.

***This blog post isn’t a comprehensive list of things to do before setting off, but rather a list of things many people don’t do enough of before setting off – they’re too focused on reading up about cruising destinations and taking their sailing courses.


While studying for your sailing qualifications, take up one of the many crewing opportunities that are out there. There’s many lonely or short-handed sailors looking for some company and help aboard their boat. You don’t need to cross an ocean, you can just give a hand at local races, go out sailing on a sunny Sunday, or take a week off to sail around the boat owner’s area.

For example, when Ryan was in his early twenties, he crewed for a man for a couple of weeks cruising the coast of Cornwall and the Isles of Scilly. Ryan wanted to learn to sail, while the man couldn’t convince his family to join him on his cruise. It was a win-win situation.

While crewing is an excellent idea, please make sure you stay safe. Accidents at sea can happen, so it’s important you trust the boat owner and their experience. If the person sounds a little weird or the boat looks in bad condition, just back out and look for someone else.

Charter A Boat

Want to know if the sailor’s lifestyle is for you? No matter how many sailing channels (like ours) you watch and books you read, you won’t know what it’s truly like until you try it. While crewing on someone else’s boat is a great way to get some experience, being the captain of your own vessel is entirely different – you’ll need to make key decisions every day, as well as care for the safety of the boat and crew. It can feel daunting to start with, so why not practice on a charter boat first? You’ll get a chance to prepare a sailing plan, choose an anchorage or marina, use the dinghy as your car, cook and sleep on board in different weather conditions, and more. Plus, if you plan to buy a recent model sailboat, you can rent and test the specific model you’re interested in.

If you’re planning on chartering a boat this year, Click and Boat have some great offers available all over the world – from Greece to the Caribbean. You can rent sailboats and motorboats alike, including some really cool catamarans. If you do decide to charter with them, it would mean the world to us if you used our referral link (this one), and let us know once you’ve booked, so they send us a referral fee 🙂 Every little helps for us, as you know 🙂


Get On As Many Boats As Possible

We all think we know what kind of boat is for us – catamaran or monohull, 32ft or 50ft. The truth is, each boat is different both in terms of handling and comfort, so in reality you don’t know what you want until you try it.

When we bought Kittiwake, we thought I’d feel less seasick on a catamaran than a monohull and that a catamaran would be more stable. However, we later spent some times on friends’ monohulls and discovered that heavier monohulls felt much more stable than light (3 tons) Kittiwake. While she was the perfect first boat for us with plenty of positive points (square bed, super safe cockpit, small easy-to-handle sails, and more), we realised that we needed something a little different for our long-term sailing plans, so we upgraded to a Tayana 37.

Find ways to step on board and sail as many boats as possible before you commit to a certain model. Here’s some ideas:

  • Find your dream boat’s owners group and ask the members if anyone is up for taking you out on a sail – everyone loves to show off their boat and you can repay them with some wine and cheese.
  • Join your local yacht club and make friends with everyone – they may take you out on their boats or let you help them with their races. You may even be lucky enough to meet some old salts that can offer you some sailing or cruising advice.
  • Check out your local sailing schools and see what sort of boats they have in their fleet – is any of them similar to the model of boat you like? Then you may want to book yourself on a course they hold on that boat.
  • Charter a boat peer-to-peer. Some companies, like Click and Boat offer boat owners the chance to rent out their boat, so they have some older models in their fleet too.

Even talking with people who own different boats is helpful, as you can ask them about the positive and negative features of their boat. Their experience is super valuable, as they have gotten to know their boat well over the years. You won’t be able to spot some of the things they say on a day sail or test sail.

Help Someone Out With Maintenance

A big chunk of the liveaboard sailor’s life is taken up by boat maintenance. There is no way around it – boats need to be kept in good condition in order to be safe to sail and for the systems to work reliably. Please don’t be fooled: even new boats need maintenance and repairs, especially those with lots of complicated systems. We met a couple who bought a boat show boat and they spent the best part of spring and summer having it fixed – a window leaked, the AC wasn’t working, the bilge pump wouldn’t work, the autopilot broke on their first long passage,… Every single boat needs antifouling, fresh paint, and new gear every now and then and things will break in the middle of nowhere, where you can’t hire a marine specialist to fix them for you. So boat maintenance is something all sailors need to be able to do.

Whether you want to learn some boat maintenance skills or see if boat maintenance is for you, offer someone local to help fix their boat up at the weekend. You can see how you like it, and they can benefit from an extra pair of hands. And if you don’t like it, don’t despair. Not many people love sanding and troubleshooting an engine problem, but they put up with it because they adore cruising.

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