Resources For Vagabonds. Sailing.

Welcome to my sailing resources page.

Five years ago I decided to learn to sail as a mechanism to work and travel. A quick Google of ‘learn to sail’ lead me to my local sailing club. There I found people happy to share their interest for free, that were forgiving when I capsized their dinghies repeatedly, and that somehow managed to keep a straight face when I told them I’d quit the day job with an aim to sail for a living. When I wavered, they didn’t say I couldn’t, so I did. 

The internet has always been a catalyst to adventures on and off the water. This resources page is a compilation of the people that have helped me on the way in sailing, professional yachting, and also inspired me. It’s a mix of practical and anecdotal that I hope readers might find useful.


Always have an escape plan from the rat race.

Fuelling the dream…

I am a self-confessed dreamer. Fortunately, sailing is full of them, so it’s easy to get away with it. Further down the page you’ll find some hard nosed pragmatism that’s essential if you want to work on boats for a living. But for now, because travel has always been my focus, I’ll stick to the raw possibility of sailing and some inspiration.

  • I met Tom and Susie in Las Palmas in the lead up to the Atlantic Rally For Cruisers, a big sailing rally from Las Palmas to St Lucia. They had both recently left their jobs with a plan to circumnavigate on their yacht Adina. Over the past three years their blog has grown into a fantastic account of their trip. One of the best on the subject and an illustration of what’s possible.

  • Guillaume Danis leads two lives, one as banker working for CreditSuisse/husband/father, the other as an expedition sailor in his Boreal yacht. I interviewed him recently for an article I was writing for Sailing Today on high-latitude sailing. Not only does Guillaume do all his adventure sailing using his annual leave from work, he also takes many of his colleagues with him as crew. Proof you don’t have to quit the day job to have big adventures on a sailing yacht.

  • Roger Taylor is the doyen of his own unique cruising style. His book Voyages Of A Simple Sailor is a cathartic read for the big boat yachtsman and an introduction to all that’s wonderful about going to sea for the beginner. Taylor goes a very long way in a very small boat. It’s almost meditative. Wonderfully written.

  • Nick Jaffe was living in Europe and decided to sail home. To Australia. He didn’t know how to sail, didn’t have a boat; yet still managed it. The film about his trip Big Oceans is well worth downloading. Tiny boat, enormous dream.

  • A new addition to the list. SailingLaVagabond is the YouTube channel of a young couple sailing their 40ft yacht and what they get up to. They now make money from their YouTube channel which gives a great, realistic, picture of the cruising lifestyle and the big adventures they have.

Start small 

Drawing conclusions too soon on what getting into sailing entails financially risks ruling you out of the equation before you’ve even started. Start small.

Two years ago I ran a beautiful Oyster cruising yacht in the Mediterranean for a really great family. At home in the UK they kept a small dinghy, which they raced at weekends. When the inevitable happened and complex equipment on board the Oyster (worth a million or so) went wrong, the owner would always say with seasoned acceptance of a yachtsman ‘that never happens on the Wayfarer.’ Therein lies a lesson, in sailing, simple can be just what you need.

I’d highly recommend starting sailing on something small and building the fundamental wind awareness that helps you sail anything well. Immerse yourself in dinghy sailing, wind surfing, or something similar- an appreciation for where the wind is coming from will be absorbed naturally.

Think carefully about what sort of sailor you think you might be. Learning to race is useful as it helps hone the fundamentals, but there are lots of other types of small boat sailing you might enjoy more.

The Dinghy Cruising Association has seen a big increase in membership recently. What’s possible with a small boat continues to amaze me. Fundamentally, dinghies aren’t just for racing; they can take you places as well.

Sailing clubs have different focusses, some just racing, some cruising, some yachts, some dinghies- take the time to find one that’s a good match.

Learning the big ropes

Leaning to sail in the English Channel. Cold, very wet, and a steep learning curve.

The English Channel, in December, living the dream.

You never stop learning to sail. I didn’t start until I was 22.

After taking a Competent Crew course and doing a bit (and I mean a bit) of dinghy sailing at my local club, I enrolled on Hamble School Of Yachting’s Professional Sail Training course. Courses like this one are sometimes dubbed, rather scathingly, ‘zero to hero’ by the bearded old guard of sailing- but everyone’s got to start somewhere. If you haven’t done much sailing before and want to drop yourself in at the deep end, so to speak, the PST is a comprehensive grounding that you can build upon. 

If you are from the UK, or anywhere in the world for that matter, the Royal Yachting Association training scheme is seen as one of the best ways of learning to sail dinghies and yachts in a structured way. I think it’s a great scheme, but it is not the be all and end all- you don’t have to have qualifications to get into sailing…


Jimmy Cornell’s ‘World Cruising Destinations’ is an encyclopaedia of sailing possibilities.

Sailing as a mechanism to travel has been at the core of this site since I started it. I am as excited as I ever was at the perspective a yacht brings on a place and the unparalleled arrivals it offers. With the basics under your belt, there is endless adventures to be had all over the world…


A moment on my first yacht delivery that confirmed sailing would deliver the interesting work and travel I was craving.

Getting ready to sail across the Atlantic for the second time. Height on a sailing yacht can be both a curse and a blessing.

A rig check before leaving Las Palmas for St Lucia.

Casting off the lines

My friend Richard Rowe runs Sailing Jollies. His events visit Europe and the Caribbean, providing an informal introduction to sailing in sunnier parts of the world. There’s tuition, but the focus is upon having a great time. 

If you’re perhaps interested in getting stuck into some serious adventure straight away Rachel Sprot’s Rubicon3 explores Morocco, Greenland, and even further afield with accredited training included. The approach on Rubicon3 is heavily focussed on adventure, with time spent exploring ashore as well as sailing.

Professionalising the dream

If you’re being paid for it, it’s work. It is fundamental to understand this. Whilst this website bridges the professional and personal without apology, I have built my references like any other job by delivering on what I have promised. It can be hard work. Without references, in yachting, you go nowhere. It’s simple, build a reputation, and the world is your Oyster…or Swan…or….nevermind…

Think very carefully about what you want. To sail for the summer and ski for the winter? To just sail for the summer and take the winter off? To bank the cash and retire early? Yachting is a sector where, once you get going, there is good potential for earning a very comfortable salary- but there’s a reason for it.

Think about your role on a boat. What do you want to do? Be a deckhand? Be a stewardess? Work your way through the career ladder to be a Captain on a superyacht? All of these are professional positions, not really gap year options due to the investment involved in the basic certificates you need to get on board, and all being very competitive to get into.

Think about what sort of boat you want to work on. Motor yachts and sailing yachts are quite different, as are classic yachts and newly built boats. Whilst many seeking their first job will take anything they can get, you should focus hard on what you want in yachting, otherwise the reward will only be financial. Though, of course that’s fine, if that’s what you are interested in. In which case, this probably isn’t the site for you.

I wanted to travel, liked the idea of the boat being powered by the wind, and so decided sailing would probably be the direction I would go in from the beginning. However, I also looked into becoming a deckhand on a big motor yacht. The two main draws were better pay and the opportunity to work as part of a big team. Neither were particularly important to me, though sailing yachts have at times been a lonely game to play.

…or travelling by sailing yacht for fun…


Think about what you bring on board. Personality is important.

People have travelled using sailing boats for thousands of years and it remains a dream to people today. What many say they would do if they won the lottery. But do you need to win the lottery? I’d argue you don’t need much money to sail around the world on someone else’s boat.

Alistair Humphrey’s, who cycled round the world and wrote a book about it, did it for under £7000. It’s more than possible to hitch around the world on yachts for the same amount. Some useful resources include:

Whilst sailing across the Atlantic sounds fantastic, and it is, you should be aware that most yacht owners do not need extra crew. You will always be expected to ‘work’ the passage, and generally won’t be accepted without at least some experience. Sailing a yacht can be very hard work for all involved and once you set off, you don’t stop. Many trying to hitch a ride at the annual Atlantic Rally For Cruisers don’t do their research into the realities of sailing. I’ve seen multi-millionaire sailing yacht owners perfectly content getting stuck in fixing things in the engine room, don’t kid yourself you won’t be asked to do the same!

…or buying one…

By far the most honest and well written account of re-mortgaging the house, throwing caution to the wind, and going sailing as a family that I have read is Guy Grieve’s Sealegs. Having spent some time in the Caribbean,  his picture of these misunderstood islands and their frustrations as a sailor really struck a cord with me. More than anything, Sealegs is a great case for buying the boat, despite it’s economic insanity, and embarking on such an adventure without hesitation.

If you are at the right stage in your life, it could be the right thing to do. But consider the following before you do:

  • Annual maintenance will cost you an average of 10-15% annually of purchase value, if you do it properly. To not properly maintain the fundamentals is extremely foolhardy, though that’s not to say plenty go to sea with boats in a very poor state.
  • Think about the yacht you buy extremely carefully. I’ve seen plenty of boats meant for sailing between Greek islands covering thousands of offshore miles. Something has to give. If in doubt, buy something smaller, stronger, and proven to look after you at sea. It probably won’t be fashionable, but you’ll feel wonderfully smug when you go through that first unexpected gale. Read a copy of Peter Bruce’s legendary Heavy Weather Sailing so you know how different types of yacht handle foul weather.
  • Do deep research into the boat you are about to buy, certainly pay for a survey, and get to know others that have the same model- people in sailing help each other.

Here’s to adventures on the water. Good luck and fair winds.

Email this to someonePin on PinterestShare on FacebookTweet about this on TwitterShare on LinkedInShare on Tumblr

Related Content

Coffee at Mach 2 ‘How do you like your coffee, Captain, - cream and sugar?’ We are at Thirsty West, the half-way point between the European and North American continents, and the stewardess in charge of the forward galley is looking after her aircrew during a pause in serving the passengers meals. Mach 2. On autopilot, 11 miles high, moving at 23 miles a minu...
Arthur Beale, London Arthur Beale is a place not many sailors know about. Incongruously located on Shaftesbury Avenue, in the heart of London's theatre land, for the past 400 years or so, is quite possibly the world's best chandlery. Behind the desk is invariably a man sporting a beard, espousing rigging screw wisdom to sailors and tourists alike. Upstairs you will ...
Vinegar and single malt in Dominica Leaning sideways over the sink, a funnel from the yacht’s well stocked galley protruding out of my ear, with a concoction of vinegar and the owner's single malt (Talisker) being poured into it- I am the first to admit the comedy of the picture that fills the mirror in front of me. However, I am in agony, so like this time last year, when I was abou...
Yachting Monthly Article I have a short article published in next months Yachting Monthly magazine on a trip I crewed on to Sweden. A title that's been printed since 1906, it's a real privilege to be featured on its pages.      

Leave a Reply

Your email address will not be published. Required fields are marked *