How to go offshore sailing

Schooner Arcturus in Auckland, New Zealand (2006)

Incredibly, it seems, I'm getting more and more emails from people looking to me for advice on how to get out and go sailing. I was in the exact same position not very long ago, and it still confounds me as to why in the world people are asking me!? But it does feel pretty cool too.

I got a recent email from a young guy in Australia looking for advice, and I asked him if I could publish our email exchange here. He said yes. This is it:

"Good morning Andy,

Sorry for bombarding you, i understand the busy life of a sailor myself. My plans have recently changed so i thought i would give you an update before you replied to my original email.

The origional plan to buy a boat has gone out the window as i was relying on a second friend to help with the investment but my goal is still to see as much of the world as I can through sailing. The easiest was i can see to achieve this by crewing / signing up as a delivery hand or even chasing some professional qualifications. Obviously paid or subsidized work would help me stay at sea for longer as i plan to make this my priority and not do other work.

Do you have any advice on training i should target, whether formal qualification of just experience? Also any sources of information such as websites i could look at?

The main qualification I can see that leads to professional work is the Yachtmaster but from what i understand you either need alot of experience behind you already or alot of money to pay for a fast track program.

Thanks again, hope your enjoying your time out on the water.


...and my response, written this morning...

"Hey Blake!

Okay, no excuses from me for how long it's taken me to reply to you! I really appreciate the fact that you took the time to write me - part of the reason I think is that it doesn't feel like very long ago that I was in your same position, writing to guys like John Kretschmer and John & Amanda Neal asking for the same advice. In fact it feels downright ridiculous that anyone is asking me for advice, because frankly I'm not sure how I ended up here! But I'll do my best to help you out, and hopefully can inspire you along the way.

First things first - no matter what you decide to do with your life, sailing or not, NOBODY is going to hand you anything. There are no secrets to success in life - I kind of compare it to losing weight or getting fit - there are no special formulas, simply eat healthy and exercise. Applying that to your case, you gotta just go out and do it. You'll be amazed at how the universe lines up for you when you put your mind to something. And furthermore, never say 'no' to any opportunity that comes up, unless your gut tells you so (for example, don't get on a shitty boat and risk your life - I've left three boats at the dock so far in my delivery career, one in Bermuda, one in the Panama Canal, so don't be a hero. You're gut will tell you when to drop it). So there's my philosophical answer.

Practically, offshore sailing is one of the easier things to do in life (generally speaking - long distance, bluewater sailing involves a lot of responsibility for the boat and crew, but not too much actual work besides sail trimming and cooking), and one of the scariest things for most people, even sailors. Which is good for you if you decide you like it - there are not that many people doing it! 

I personally think the best way to get offshore is to volunteer as a crewmember with either a delivery (be careful, some delivery skippers are real jerks), or a family on an extended cruise (again be careful here - if they have kids, make sure you get along with them!). I personally like taking new people offshore on deliveries as a 3rd or 4th crewmember because I enjoy the training and I love sharing my passions with other people. And since they're the 3rd or 4th, I know that the mate and I (who is usually my dad or someone I pay with professional qualifications) can sail the boat 2-up if the new person is totally useless, there isn't much risk involved. Expect to pay airfare to and from the boat in such cases, but the captain/owner should pay for your food and living expenses onboard. 

There are two ways of doing this - sign up for online websites ( is probably the best and cheapest) or simply get out and meet people on the water. When I lived in Brisbane during a semester of uni, I'd take the train to the coast and go racing on Wednesday nights just to get out sailing and meet people - you never know where those opportunities might lead, who you might meet. The online stuff is pretty tough to do if you go in cold, meaning you have no connection to the boat or anything - it's hard for you to judge the boat and skipper, and it's hard for them to judge you without a reference. So sometimes dock walking works better, particularly in places like Bermuda out here where it's a way-station for people moving boats around. I will also always post crew opportunities that come my way on my Facebook page, so keep and eye out for that.

I'd avoid the professional route until you get some miles under your belt. I did the Yachtmaster and it's expensive, and you're right, you need lots of miles or lots of money for the fast track. You can earn the experience first by pursuing volunteer gigs, then go and get the license if you think you want to continue with it. 

The rally boats are the best way to crew because you know they are well fitted out - we require certain safety gear at a very high level. The skipper might be lame, but you can feel good knowing the boat and it's gear is in good shape.

Hope that helps!