Advice For Aspiring Cruisers – Sailing Away

Once you’re hooked, there’s no turning back. You’ve watched all the sailing vlogs, read a lot of blog posts and magazine articles, asked for advice on forums, and bought some books on navigation. Now the dream of sailing away is getting more and more tempting and the more you look into it, the more it seems doable. You’re inspired, but you haven’t started getting ready to go just yet. Is that you? Then read on – we’ve got some advice for you.

Sunset Laredo

The boat is never ready

Ask anyone who’s ever crossed an ocean and they’ll tell you their boat wasn’t 100% ready when they set sail. Of course it was ready and well equipped to cross an ocean, but was it the best it could be? Nope. No boat, not even a spanking new one, is ever the best it can be. There is always ways to improve it.

While it’s important that you get your boat as ready as you can and don’t neglect big jobs you’ll then have to do while cruising, it’s equally crucial to put things into perspective and understand what is a good level of preparation to get going. Don’t get fooled by advertisements – brands need to sell stuff. Research your cruising grounds carefully, compare them with what’s advised by authoritative sources, such as Skip Novak or the ARC checklist, and apply some good old common sense. You’ll end up with a well-set up boat.

Sanding the boat

Experience comes from doing

While it’s great to take some courses to get the basic knowledge covered and build some confidence, experience is worth so much more. You won’t become any better at sailing by waiting a little longer on land.

Get out there and start building some experience. There are many ways to practice sailing without owning a boat. Rent a boat, crew on an ocean crossing, or hitchhike on other boats. Real life experience will teach you much more than any course. Don’t forget that once you buy your own boat you’ll need to get to know it inside and out and that will only happen if you sail it.

Ryan sunbathing

Smaller is easier and cheaper

We’re big advocates of the Pardeys‘ motto: “Go small, go simple, go now.” While we understand that some people cannot put up with a 26ft boat with little standing room like ours, it’s also true that you really don’t need to buy the biggest boat you can afford. A smaller and simpler boat is easier to handle, more fun to cruise on, and cheaper to buy, run, maintain, and moor. A smaller boat will take you to more places – they can get you closer to shore, enter shallower bays, and it’s easy to find a spot in a marina for them.

Some sailors and cruisers end up bankrupt or need to sell their boat or go back to land, disappointed they couldn’t make their dream last and bitter about the enormous expenses they need to pay for their boats. These are the kind of people who say “boats are money pits.” Some of these people bought bigger boats than they could afford to look after, some bought vessels with very complicated systems which easily break down and need lots of professional maintenance, some bought boats without getting a proper survey done. Don’t make these mistakes – go as small and as simple as you can put up with. You won’t regret it. And don’t forget that boats will almost always sell for less than what you paid for, no matter how much money you put into them. The fun and amazing moments you have on them always pays off for that.

It’s not always easy and fun

Cruising makes for a great lifestyle – you get to spend a lot of time outdoors, you have a lot of free time, you see amazing nature phenomena, and you travel to places on your own terms. However, it’s not all fun and games.

Life at sea can be dangerous and tough. Be prepared to handle stressful situations, make hard decisions, resolve conflict swiftly, feel cold, wet and dirty, and get frightened. Things can go seriously wrong out of the blue. No matter how amazing some days are, there will be hard times, and those can make or break a sailor.

Sinking boat

The money is never enough

This is kind of a cliché, but it’s very true. If you worry that the money you have isn’t enough, be warned – once you save a bigger amount, that won’t seem quite enough either. There’s always a bigger boat, more gear, and better instruments you can buy, and bigger plans you can make. If you procrastinate thinking you can do better if only you make another $10K, you will never leave.

Our advice is to establish what is acceptable to you and what you can live with. Safety is paramount, so make sure you have the right gear to suit your sailing adventure, but don’t overbuy. Do you really need all the latest gadgets? Do you really want to spend every single night in a marina? Do you really need to spend $2K per month? The more frugal you are, the sooner you’ll set off. If you’re wondering how much money you need to spend each month and keep in the bank once you set off, we talk about it in this blog post.


Set a deadline

The only reason why Ryan and I are out here, living this life, is because we set a deadline. Once we made the decision and figured out how to make money from the boat, we set a firm deadline for our departure. I honestly believe that if we didn’t set the deadline, we’d still be in our offices in Manchester.

Setting a date means you can work backwards from that day and establish every single thing you need to accomplish before it. When we started getting ready, we had a massive spreadsheet with tasks, estimated time of completion, and dates on it. Having mini deadlines for everything meant we felt motivated even on those nights and weekends where all we wanted to do was relax. Preparing for leaving while working full-time wasn’t easy, but it was all worth it, as it allowed us to leave sooner and save up more.

Lizzie G Portugal

So what are you waiting for? Turn your dreams into reality and get going. There is no better time than now. Good luck, and fair winds.

  • Elizabeth

    I would love to learn how to sail, but it seems so complicated and I genuinely have no idea where to start so I still don’t know. What a wonderful thing to be able to do though, to just go anywhere….

    1. Sailing Kittiwake

      Hey Elizabeth, we all started from exactly where you are. All the best sailors did.
      We didn’t know much about sailing at all when we bought our boat, but you learn by reading and doing 🙂 Don’t let that put you off. The incredible rewards are worth the effort. Start off by going on a sailing weekend trip, either with the RYA, or through personal connections. You’ll get a feel for what’s involved. Then you can build it up from there if you like it 🙂 Some people prefer to take courses, some prefer to learn on their own. Find your own way.

  • Ellen @ The Cynical Sailor

    Our first boat was 26′ and we made it work. It’s amazing what you can do without and how you adapt to the amount of space you have. I’m glad we went with something smaller and cheaper so that we could get out there earlier rather than waiting for the perfect boat.

    1. Sailing Kittiwake

      Yes! Go small, go simple, go now! 🙂

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