Make A Living Sailing

Can You Really Make a Living Sailing Boats?

By: Learn To Sail

It’s a question many of us ask ourselves when we are out having an amazing day on the water. Can I earn a living out here rather than that carpet-lined cubicle that has sucked at my very soul like a demon leech? Well, you probably can, but it will take a little bit of doin’. Here are some thoughts that might shed some light on the prospect of sailing as a livelihood.

Make A Living Sailing - Education


Of course we have to say this but it’s true – ASA certification and training is where it all begins. Find a local school that teaches sailing through the ASA method and start checking off the certifications. Once you accumulate the hours and the certs, you’ll begin to know if the reality lines up with the fantasy. Learn more about why ASA Certification is important ⟩⟩

Make A Living Sailing - ASA Certified Instructor

Certified ASA Instructor

Once you have some solid knowledge, start hitting up the local schools and see if they need a 101 instructor. It’s quite common for schools to need a people-loving, sailing-loving person to show newbies the ropes… or “lines” as the case may be. Teaching at a small school is a great way to keep your hands on the stick and sailing everyday. Building on-water hours is key. Become An ASA Certified Instructor ⟩⟩

Make A Living Sailing - Delivery Crew

Delivery Crew

One thing about sailboats is they often need to be moved around and most owners don’t have the time to make that happen themselves, so delivery captains and crews are a necessity. Keep a look out for long-distance races and find out if anyone needs a hand bringing the boat back. Also folks who buy boats far away need people to bring the boat home. If you’re certified and have a good amount of hours under your belt, you’ll get a spot. It’s pretty cool – delivery crews get to see some exotic places and sometimes get to ride on some pretty nice boats. Granted, it’s very often an upwind beat with the iron genny chugging away, but it is a far cry from the aforementioned cubicle with ringing phones and stacked up email.

Make A Living Sailing - Captain

Obtaining a Captain’s License

To open up your horizons to the fullest, getting a captain’s license is a must. It’s not easy, but once achieved there will be far greater opportunity and more money. Of course that money and opportunity comes with the price of infinitely more responsibility, but if you’re cool with that, you’ll have some choices. Depending on the level of captain’s license you end up with, you can do anything from running a little charter cat in the BVIs to skippering Larry Ellison’s private 150-foot ketch and all points in between.

Make A Living Sailing - Racing


This one is tough to be sure, but there are definitely some people that are out there making a living racing sailboats. These days, rich owners who want wins will pay to increase their odds. Gone are the days when top sailors like Gary Jobson would sail with the Ted Turners of the world for sandwiches and hotel rooms. Today, paid racers with proven track records are bouncing around, going boat to boat, trying to help the cause. Perhaps the crossover of boat manager/afterguard is more common, but just being a sailboat racer isn’t out of the question for the very talented.

Make A Living Sailing - Business

Own a Business

Starting your own business might be one of the best ways to make a living sailing. Many a former instructor has taken the plunge and started up that sailing school biz and lived happily ever after. True, there is payroll, boat maintenance, scheduling and all of the tedious things that go along with owning any business, but you will be outside and you will definitely do some sailing. It takes a plan, commitment and guts to begin an enterprise, but that all comes a little easier when the prospect is built around a passion – we say, go for it!