5 Ways to Get Offshore Sailing Experience as Crew

how to get offshore sailing experience“How do I get experience sailing offshore?”

Many Sail Mentor readers are planning to do ambitious things in their sailboats, including crossing Oceans (or at least Seas).  Jumping off into the great blue yonder at the helm of your own boat is a romantic and achievable dream, but few people want this to be their first time in blue water.  So how do you get some experience so you’ll know what to expect?

Once you’ve learned to sail and spent some time learning seamanship in your own sailboat, the next big step is to go do a big, multi-day trip out of sight of land.  But how do you do that?  Here are 5 methods, listed in ascending order of risk factor.

I’ve personally done numbers 1,2, and 3.  After taking my Offshore Certification course, I sailed south on a 32′ classic double-ender with tan-bark sails.  The next year, I sailed north in a 60′ state of the art ocean racing machine.  The mainsail on the second boat was worth more than the entire first boat!  The two experiences were very different, but I wouldn’t want to have missed out on either one.

1: Take an Offshore Skipper Certification Course

There are many offshore certification courses you can take.  I did the Sailing Canada Offshore Skipper course about 7 years ago.  The American Sailing Association ASA 108 course is similar. The Royal Yachting Association has a Yachtmaster Ocean certification which is set up a bit differently.  You need a certain amount of experience and then challenge the practical exam.  There are many RYA schools that provide training to prepare you for the test, though, and this certification is respected all over the world.

I did my course on the West coast of Vancouver Island.  We ventured out for a few days where we stood watches and fixed our position using the sun, a sextant, and a watch (celestial navigation is a required element).  It was a great experience and I’m glad I did it.


  • You know exactly what you’ll learn and that the skills and methods are approved by a national sailing association.
  • You know the skipper is a skilled professional who’s done this many times before and the boat will be equipped and maintained to a higher standard.
  • Simple to find and book a trip.
  • You get a snazzy certificate which might help you when looking to crew on other trips in the future.


  • Expensive (mine cost close to $2000 for a week).
  • You will need to complete many prerequisite courses.  This is only a “con” if you’ve been self-teaching yourself or gaining experience through mentorship.  You may be able to do the course anyways and just not receive the certificate at the end.
  • You don’t get to choose who the rest of the crew is that you’re doing the trip with.

2: Pay for an “Offshore Experience” Trip

There are many people who either take on paying crew for passages or run blue water charter trips with their boats.  The purpose is to give people the experience and teach them skills, but the syllabus will be created by the people running the trip, so will vary widely.  It’s more important to do your homework for these types of trips.

Two organizations that are well known and have a good reputation are Mahina Expeditions and John Kretschmer Sailing.  These are just examples, though, and there are many others.

I purchased one of 4 crew positions on a run from Bermuda to Lunenburg on an Open 60 racing sailboat with one of my personal sailing heroes, Derek Hatfield, on his rocket ship, the Spirit of Canada.  It was an intense and amazing 725 nm trip in 4 days.  We hit 27 knots one night while surfing under only a quadruple reefed main.  It was an experience of a lifetime and well worth the $3000 price tag!


  • If you do your research, you’ll end up with a very experienced skipper and well equipped boat.
  • It’s simple to find and book a trip.
  • There’s a wide selection of exotic locations and boats to suit your taste if you dig to find them (did I mention 27 knots?).


  • Expensive
  • You don’t get to choose who the rest of the crew is that you’re doing the trip with.

3:  Join a Boat That’s Part of an Organized Cruising Rally

There are “cruising rallies” all around the world.  These are organized groups of boats who do a crossing or cruise an area at the same time.  They stay in contact and are sometimes run as an informal race.  There are always good parties at the end.  New cruisers often use a rally to give them a feeling of safety and camaraderie.  New cruisers also often want to take crew along to make it easier to run watches and handle the inevitable things that go wrong during a long crossing.

You can either contact the organizers of the rally, or just show up in the weeks before the departure and walk the docks and hang out in the local pubs looking for a crew position.

Some of the larger rallies are the ARC (Atlantic Rally for Cruisers) which crosses from Europe to the Caribbean every November, the Baja Ha-Ha that goes from San Diego to Cabo San Lucas around the end of October, and the Pacific Puddle Jump which is more informal and leaves from Pacific Mexico and Panama for French Polynesia between February and March.


  • Most rallies have minimum requirements for their members’vessels as well as training, professional weather forecasting, and tracking.  This gives you some added assurance that your skipper won’t get into too much trouble.
  • Rallies do big crossings to interesting places.
  • There will be a lot of different boats leaving from the same place at the same time, so you may be lucky enough to meet different skippers and find a boat that will be a good fit.
  • Your passage will usually be free (though you’ll need to pay for airfare on both sides).


  • Many skippers will be relatively inexperienced.
  • These are often long trips, so you’ll need more time off work (don’t forget to leave a buffer in case winds are light and it takes you a while to get there!).

4:  Find a Friend or Acquaintance who Needs Help on a Crossing

It’s very common for people to need a hand on a large trip, especially for their first big offshore trip or to move a boat they’ve just purchased.  Once you’re a little bit plugged into the sailing scene from owning your own boat or racing, you’ll start to hear of opportunities to take a week or two off work and give somebody a hand.

One common need is racing boats that need to get to the start line or home from the finish.  Put the word out among your racing friends that you’re available for deliveries.

My first long offshore passage was from Victoria to San Francisco with two other guys on a Westsail 32. Terry, the skipper, needed to move his boat South and had never been offshore before.  His girlfriend had little sailing experience, and they made the wise decision to not have her along on this potentially nasty stretch of water, so he needed a couple friends to give him a hand.

It took us 8 days to cover the 800 miles.  We sailed South along a line about 100 miles off the coast to avoid the lee shore and confused seas closer to the coast.  We entangled the prop with a spinnaker line on day 2, so we were truly a sailboat until a week later when we sailed onto anchor under a starlit sky in Drake’s Bay just North of San Francisco.  It was a magical moment as we entered the big, empty bay under sail, just like Sir Francis Drake did 400 years ago.


  • You know the skipper and the boat and can decide if you will be a good fit on the trip.
  • Your passage will usually be free and you might even get your friend to help with airfare.
  • This is a true independent adventure.  There’s no external sailing school or expert looking over you.  You and your skipper are doing this for real.


  • Your skipper might be inexperienced and the boat may not be up to the task.  You need to take responsibility for making sure that you will be safe by asking the right questions.  You might want to consult a trusted mentor to be sure.
  • You need to be lucky enough to stumble across an opportunity.  The longer you’re involved in the sailing community and the more trips you do, the easier it will be to find opportunities.

5:  Find a Crew Position on the Internet

This is my last choice, but is often the first thing that people think of to get blue water sailing experience.

There are a number of websites and forums that allow skippers to post looking for crew and vice versa.  I’ve never used any of them myself, but I can recommend two based on recommendations of people who have:

Cruisers Forum:  I’m a long-time member of Cruisers Forum and it’s a great community.  However, I don’t recommend that you pop on there and post that you are looking for a crew position right away.  Instead, spend some time posting and getting to know the folks on the forum (and letting them get to know you).

Over time, you’ll get to know the people there and when an opportunity comes up, you’ll know which skippers you’d be comfortable going offshore with (and they’ll know a bit about you and whether you’ll be a good fit on their boat).

Sail OPO:  This is a paid service that matches crew with boats.  Hank Schmitt runs the site and by all accounts puts real effort into screening skippers and crew and finding good matches.

There are also just some amazing random things that come up from time to time.  Here’s an opportunity that came up last year for a crew position through the Northwest Passage!  How’s that for a once in a lifetime opportunity.


  • Lots of opportunities are available if you dig around.
  • Many crew positions will be free. Crew positions that pay for your airfare or even a stipend will come up from time to time, but will usually be tough to get unless you already have a lot of experience.


  • It’s tough to know what you’re going to get.  You might show up to find a poorly equipped boat or nut-case skipper.  Even if you’ve just spent a lot of money to fly in, insist on going for a short “get to know you” sail first and then feel free to just leave if it’s not a good fit.  Don’t put yourself at risk.  You obviously need to take special care if you’re a single woman.

Whichever way you choose to get out and get your first experience, it will get easier and easier to find crewing opportunities as you gain experience and expand your network of blue water skippers.

Have you been crew on an offshore sailing trip?  How did you find the opportunity?  How did it work out for you?  Tell us about it in the comments below.

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5 thoughts on “5 Ways to Get Offshore Sailing Experience as Crew

  1. Operating the boat on my own was quite an experience today. I kept aknsig myself: What did Frank say to do?I got into trouble pretty fast. After being reminded on almost every lesson not to go near the rocks guess what I ended up over near the rocks. The wind was very light while I was going North out of the marina. There was traffic coming toward me so I decided to get to the right.The boat was moving real slow so I decide to tell my buddy to raise the jib. I made a big mistake and told him to pull the jib sheet on the wrong side. The boat immediately turned right toward the rocks. That’s when panic sets in and you try to remember everything you have been taught. I had my buddy let the jib out and he tried to drop the main sail as fast as possible. In the mean time I got the motor started but it wouldn’t go in forward gear. The boat had spun around and the stern was towards the rocks and the wind was coming over the bow. I had the motor rev’d all the way but the boat wasn’t moving. I was able to get the boat repositioned by paddeling away with the tiller/rudder. Once I cleared the rocks by a safe distance I was able to calm down, put the main sail back up and sail back to the dock. The dock hand confirmed the motor wasn’t working in forward gear which made me feel a little better.It’s amazing how everything comes back to you when your adrenalin is pumping. I’m sure my gaurdian angel was just messing with me that day.I wasn’t deterred though. We got another boat and went right back out again. I made sure the motor not only started but worked in forward gear. The rest of the day went fine and we made it back to the dock with a great My first solo story .

    1. Well, that is one heck of an outing. Good on you for getting out there and trying again! That took courage. At the end of the day, though, you were in a safe situation where the worst case scenario was denting a rental boat on the rocks. Just getting stuck in and figuring things out seemed to work out!

      Just remember: When the poop hits the fan and you decide to start the engine, always take 30 seconds to check the water for ropes. That’s usually the time somebody has let a line go overboard and you wrap the prop!

  2. In addition it requires competent crewmembers to understand ‘taking a turn’ around a cleat and to be able to make cleated lines secure. Lines and halyards need to be coiled neatly for stowage and reuse. Dock lines need to be thrown and handled safely and correctly when coming alongside, up to a buoy, and when anchoring, as well as when casting off and getting under way.

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