People are often surprised to hear that I’ve never been motivated by an adrenaline rush or thrill-seeking of any kind. During my solo around the world voyage and all the sailing I’ve done since, I have enjoyed hair-raising days of surfing huge Southern Ocean waves and pushing boats to their limits in the name of speed. But the moments I really cherish are the ones when I’ve felt complete confidence in the boat under me and the crew’s ability to handle any situation. It might not sound very exciting, but it’s an incredible feeling when you’re in the middle of an ocean, days from help but completely comfortable and self-reliant.

It’s also a feeling which is only achieved with equally unexciting, occasionally tedious and very thorough preparation. You’ll be hard-pressed to find a truly experienced sailor who doesn’t take preparation seriously. There’s nothing worse than setting off on a sailing holiday, only to be interrupted by broken equipment or unexpected dangerous weather.

So if you’re heading out to sea, I’m going to assume that your boat is sound and well maintained and run through a few things you’ll want to consider.

KEEPING WATCH

Depending on the number of crew and their ability to handle the boat, you might choose to keep watch alone but preferably you’ll share watches with at least one other. The crew’s ability and weather conditions will also dictate the length of watches. The least popular watch is, of course, the early hours of the morning before the light of the new day. If you draw that short straw, make sure your pockets are stashed with sweets and there’s caffeine on hand.

The change of watch is another thing to think about. After hours of cold and wet, those last few minutes of a watch can drag by. Even the most patient sailor will be agitated as the new watch slowly struggles into their wet weather gear, so think about how long it’s going to take to get ready and ask the previous watch to wake you with enough time. Some sailors like to sleep in their boots and can be ready to go on deck in a few short minutes, but there are those who like to take a full 20 minutes to find fresh socks and make themselves a coffee before clocking on.

I’m one of those who prefers to sleep in all my gear, happy in the knowledge that I can be on deck in a heartbeat. The discomfort of sleeping in a harness is far outweighed by the comfort of knowing you won’t be caught off guard.

Please don't do anything crazy like take sleeping pills off watch. Problems at sea are challenging enough without being drugged into a dopey state when the skipper calls for all hands on deck.

SEA SICKNESSES

A stomach-churning topic but not one you’ll want to leave to chance. Be wary of anyone who says they don't get seasick; maybe they don't, or as many an old sailor likes to say, maybe they haven't found themselves in a big enough sea in a small enough boat.

Seasickness isn’t unusual and it's nothing to be embarrassed about. Some of the world’s best sailors get a little green at the gills, and I know someone (Cas!) who kayaked across the Tasman despite being prone to chronic motion sickness. When I was younger I would spend the first few days of a passage pretty green, but with a bit of discipline to keep myself hydrated I could do everything necessary.

The key is to find what works for you. There are some great products available so shop around and test them out before you leave the dock. A few of the tablets I’ve taken have been incredibly effective; however, their effectiveness was largely thanks to their ability to put me to sleep, so be wary of side effects.

KEEPING WARM AND DRY

If you’re planning a passage in the tropics you can skip this section, you lucky thing!

Having grown up in Queensland, I don’t handle the cold well so I appreciate quality wet weather gear. Take your time trying on jackets, and think about the benefits of a smock versus zip front. When it comes to sea boots, the cheapest option is often surprisingly sufficient. But to get the very best, you’ll need to spend top dollar.

Some ladies like to wear drop seat overalls, but there’s a reason why many of the world’s top female sailors don’t wear them. The benefits just don’t weigh up against the risk of any water getting in.

Keeping your hands warm is tricky because they will be wet, working with lines and even the most expensive ‘waterproof’ gloves are unlikely to be 100% effective. After years of asking professional sailors, cruisers, and Southern Ocean fishermen, the only two things I would recommend are well-fitted neoprene diving gloves or sturdy plastic washing up gloves. The later is my personal preference, worn with a light lining glove if really necessary. Of course, they’ll wear through pretty fast but till then they’ll keep the wind off and won’t break the bank to replace.

MENTAL PREPARATION

This isn’t something that is normally mentioned in passage planning discussions, but I believe that it warrants some thought. Your average sailor, boatie or Aussie isn’t typically keen to talk about feelings. But faced with challenging weather, little sleep and cramped living conditions, your crew’s headspace is critical to the success and enjoyment of your passage.

I’d recommend talking to experienced sailors, as knowing what to expect can be comforting and learning about the way others deal with challenges may be helpful. Choosing crew who have proven to be resilient in tough situations is important as you may not have the luxury of pressure testing every crew member. But if the crew member understands the challenges they may face and is still determined to come, then there is every chance that they will perform well.

FOOD

As soon as word gets out that you’re planning a passage, you’ll be swamped with suggestions on what food to pack and how to prepare it so I won’t say too much on this topic. You’ll need to think about your own preferences and the facilities you have to work with. Some boats are lucky enough to have a large fridge and freezer capacity, ovens and microwaves, while others may only have a little single burner.

Remember that anything more complex than reheating food will be messy and possibly hazardous in rough conditions. I’d highly recommend a good travel mug; in big seas, it’s the best thing to use to eat breakfast, lunch or dinner. The ideal mug will have a wide base and a secure lid. Be wary of cheap plastics that hold the flavour of your previous meal or drink.

SAFETY

When it comes to offshore sailing or boating, a cautious approach is never a bad idea and in my experience can even prove beneficial to a racing sailor. During the 2011 Rolex Sydney to Hobart, my youth crew discovered that reefing early improved the boat’s performance in a steep sea and we were able to make gains on many of the experienced inshore sailors who flew more sail.

On the subject of sails, storm sails absolutely must be hoisted before heading out to sea. Many sailors have storm sails, still crunchy and new, but surprisingly few of these sails have been fitted in a way that will allow the crew to safely use them in the conditions they are designed for.

As for more general safety equipment, put together a solid first aid kit and a grab bag in case you have to abandon ship. Tie wooden bungs next to your seacocks and check that your life raft is very well strapped down. Every boat and sailor will have different communications equipment and preferences. Of course, you will need to cover the essentials like EPIRBs and VHF radios, but after that it’s up to you. The important thing is to have multiple options and backups.

A man overboard drill is another critical exercise that I’d highly recommend practicing more than once. Rather than meticulously preparing for the first drill, try catching your crew off guard and then build on what you learn. Think carefully about the placement of clip-on points and jacklines to allow you to move easily around the boat. Clipping on needs to be stamped into your muscle memory. You should feel naked without your harness and lanyard.

Also, sorry to mention such an unglamorous subject, but I have a problem with guys “visiting” the side of the boat. I’ve heard many tragic stories which resulted from this habit. So guys, please remember to tell someone what you’re doing, clip your lanyard on and be cautious—even on a nice day.

There are a million more things I could mention in regards to safety, but you’ll be fine if you value seamanship above speed, luxury or ego.

WEATHER AND NAVIGATION

When you’re at sea, you are completely at the mercy of the weather. Thankfully, there’s no shortage of good weather forecasting available. Pilot charts showing seasonal averages are a great place to start. Based on your experience and the capability of your boat, you’ll need to consider your limits and decide what conditions you’re prepared to deal with. On Pink Lady, the boat I sailed around the world, I was happy to (well, maybe not happy to, but prepared to) face over 60 knots of wind and 10-metre waves, but on your average club racer I’d be terrified to leave smooth water.

When it comes to navigation, you can choose from a chartplotter or any of the software available. It’s important to again have contingencies for navigation. Paper charts are of course a good backup, but more and more boaties are also using Navionics on their iPhones and iPads.

With all this talk of cold, seasickness and sleep deprivation, I hope I haven't made offshore passages sound terrible. I’ve always found it better to tackle the tough stuff head-on so you can get on with enjoying the passage. At sea you’ll soon adjust to haphazard sleep, find your sea legs and come to appreciate the simplicity of life at sea.

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Passage Planning with Jessica Watson: 7 Things to Consider