The Top Four Obstacles to Sailors Wanting to Go Offshore, and How to Overcome Them

Many coastal sailors, whether experienced or novice, have a desire to try offshore sailing. If you share that dream, but haven’t made it a reality, it may be that you don’t know where to start, or have found obstacles in your way.

You shouldn’t let that stop you. There are ways to fulfill your dream, and join the others who have left the shores to sail the world’s oceans.

After talking to hundreds of offshore sailors – men, women, couples, families, groups of friends – about the obstacles they had to overcome, four things came up over and over again.

 Top Four Obstacles11

  • Time
  • Money
  • Experience
  • Suitable Boat

This might seem obvious, but remember: every sailor we talked to had to overcome one or more of these.

And so can you.

You just have to decide that you want it badly enough, and make your dream a priority.

There are lots of examples of people who have done this.

In Beer in the Bilges, we describe how actor Hal Holbrook overcame the problem of a lack of offshore experience. He asks co-author “Hollywood” Bob Rossiter, a veteran offshore sailor, to accompany him aboard Yankee Tar on his first offshore voyage from California to Hawaii.

That experience gave Hal the confidence to fulfill his dream of competing in the 1980 Transpac Single-Handed Race from San Francisco to Hawaii, and later to sail with Bob all the way across the Pacific to New Zealand.

Co-authors Alan Boreham and Peter Jinks both tell how to overcome the lack of a boat by sailing other people’s boats as crew for offshore voyages.

We also include a chapter about Gary Green, a New Zealand farmer whose first offshore experience almost cost him his life. After surviving a shipwreck and nine days in a life raft with the ill-equipped yacht’s owner and two other crew, he carries on to build his own super-tough yacht, Heartbeat, and become a lifelong ocean sailor.

So how did all these sailors we talked to overcome the obstacles to their dreams?

  • Time

    • Reset priorities
    • Do a short trip, or do a longer trip in legs
    • Postpone until you have more free time (e.g. retirement, between jobs/contracts)
    • Home-school children
  • Money

    • Reset priorities
    • Manage expectations
    • Work while traveling (officially or unofficially)
    • Lease or charter a boat instead of buying
    • Crew on someone else’s boat, or take paying crew on your boat
    • Become a boat delivery skipper or crew
    • Film your adventure
    • Crowd-source your dream
    • Use a social media page to seek sponsorship for your voyage
  • Experience

    • Take training courses
    • Crew on other peoples’ boats, including offshore
    • Sail on your own boat
    • Hire an offshore skipper, crew

Part of your education comes from reading about offshore sailing.

Peter, Bob and Alan have put together a list of must-read books for you here.

In summary:

A place for  contemplation

A place for contemplation

  • Make your dream a priority.
  • Learn as much as you can before you go.
  • Be sure that the boat you’re going to be on is up to the task.
  • Benefit from others’ experience. (you don’t have time to make all the mistakes yourself!)
  • Make your life what you want it to be.

If you do this, you can make your dream a reality.


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