Start Sailing with Zero Experience

Learn the practical steps to begin sailing from scratch—with a few real-world examples from our own journey.

When we first decided to “sell it all and sail away,” we had no experience. No boat. No plan. No idea what we were doing. Our only time on the water had been in canoes, kayaks, and the occasional fishing trip. Sailing full-time sounded like a cool way to explore the world with our home, and dogs, in tow—but we had to figure it out from the ground up.

If you’re in a similar place, good news: you don’t need a boat, a background in sailing, or a huge budget to get started. Here’s a practical, beginner-friendly guide to getting into sailing—with a few examples of what worked (and didn’t work) for us along the way.

Understand What Sailing Really Involves

Sailing isn’t just one thing. It’s many things—day sailing, cruising, racing, living aboard—and not everyone shares the same dream. Some sailors never leave their bay. Others race competitively but never anchor overnight. Many live on boats full-time without ever crossing oceans.

Day sailing the first boat

We tried as many styles as possible to figure out what suited us best:

• Day Sailing: This is how we started—short outings in our local waters - the Straight of Georgia. At first, we didn’t even have the confidence to anchor overnight, so we’d sail close to the marina and come back before sunset. Over time, those sails got longer and eventually became weekend - then weeklong - trips.

• Racing: We joined local race crews. This fast-paced environment was a crash course in sail trim, teamwork, and boat handling. It’s also a great way to gain experience without owning a boat.

• Living Aboard: Before we ever “cruised,” we moved aboard to get used to life in a small space. This helped us get comfortable with maintenance, storage, and systems before adding the complexity of travel.

• Cruising: Our long-term goal was to live aboard full-time and travel slowly. Today, we typically stay weeks or months in each anchorage and only cover about 3,000 nautical miles per year.

  
  

In short, try different types of sailing to find what appeals to you before committing to a particular boat or lifestyle.

Learn the Basics

We originally planned to take formal sailing lessons, but pandemic restrictions had other ideas. Instead, we found a local couple offering lessons through Craigslist. Some might raise an eyebrow—but it turned out to be the perfect, low-pressure way to get our feet wet.

Later, we took a certified CANsail course. It covered many of the same practical skills, but added essential theory like navigation, right-of-way rules, and emergency procedures. Plus, it gave us confidence—and documentation.

Affordable, even free, learning options for beginners:

• Certified sailing courses (ASA, Sail Canada, RYA)

• Weekend or evening classes through community centers

• Online resources and books, like The Voyager’s Handbook

• YouTube channels, such as Sailing Virgins for mooring and anchoring tips

Some handy books to have onboard

You can build a solid foundation even before stepping onto a boat.

Hands On—The Best Way to Learn

Hands-on experience is key. We learned the most by simply sailing our boat. But if you didn’t happen to buy that Craigslist boat, get on as many boats, in different conditions, with more experienced sailors for that hands-on experience.

Crewing on race boats has been some of the most fun we’ve had sailing

Get hands-on, onboard

• Crew on race boats: Yacht clubs often welcome new crew members—especially in shoulder seasons when fewer people want to sail. That’s how we gained experience trimming sails and reacting quickly under pressure.

• Volunteer at yacht clubs or sailing schools: Great for networking and finding people who need crew for day sails or short passages.

• Join sailing associations: Organizations like the Bluewater Cruising Association are a great platform for networking with aspiring cruisers and experienced sailors.

• Online platforms: Sites like CrewSeekers or FindACrew, and Facebook groups dedicated to sailing or crewing, can match you with boat owners looking for help.

Build Land-Based Skills That Pay Off Afloat

While you’re building sea time, there’s a lot you can do from land to prepare:

• Navigation: Learn to read nautical charts, use GPS/chartplotters, and understand weather forecasts. These are crucial skills that we use almost daily.

• Knots: Get to know basic knots. Gooogling “how to tie a bowline” each time you need to tie something is not only embarrassing, it can be dangerous in an emergency.

• Boating safety and etiquette: Understanding “rules of the road” (COLREGs) and proper onboard behavior helps avoid mistakes—especially when crewing on someone else’s boat.

• Maintenance skills: Mark took every course he could find in relation to maintaining a boat - engineer repairs, VHF, radar and electrical to name a few.  On our cruising boat, that knowledge has saved us both time and money.

You don’t have to be an expert—just start learning the basics. It adds up quickly.

Reading charts is a skill

Do You Need a License or Certification?

Depending on where you’re sailing, a license might not be required—but it’s still worth having.

In Canada, a Pleasure Craft Operator Card is mandatory. It’s a simple test but includes useful knowledge about safety and regulations.

When we tried to check out of Mexico, the authorities wanted to see proof that we knew how to sail. Thankfully, we had our CANsail certifications and operator cards. Others weren’t so lucky—they had to get “creative.”

Certification can also help with chartering boats as well as obtaining insurance.

We’re glad we took the time to get certified—even if it wasn’t strictly required everywhere we went.

Knowing how to fix your own things - invaluable

Budget-Friendly Ways to Start Sailing

You don’t need a yacht to start sailing. In fact, you don’t need much at all.

• Join a sailing club: Many offer affordable memberships with access to boats and lessons.

• Crew for free: Some skippers will take on beginners, especially for races or casual day sails.

• Borrow or rent gear: Invest in a good life jacket (because, you know, it might save your life) but don’t invest in expensive foul-weather gear right away. You can find what you need in your closet, second hand store, swap meet or even local sports store. You don’t really need that Gull or Helly Hansen jacket right away.

Nothing fancy needed - except the lifejacket. Don’t skimp here.

The barrier to entry is often lower than people think. Start small and build over time.

Common Mistakes to Avoid

We made plenty of mistakes early on—but here are a few we’d recommend avoiding:

• Buying a boat too soon: Our first sailboat was inexpensive and a great learning tool—but we didn’t buy our full-time cruising boat until after gaining real experience. In hindsight, we might have even looked at different boat styles had we known more about sailing (but we certainly don’t regret our boat).

• Trying to learn everything before starting: You’ll never know it all. Learn the basics, then build experience over time. Remember: sailing isn’t hard - sailing well is.

• Overpacking: Pack light and bring soft bags. Boats are small and often have limited space.

• Ignoring etiquette: Don’t board someone else’s boat without asking. Respect the captain’s authority. These little things go a long way.

Mistakes are part of learning—but avoiding the common ones will make your journey smoother.

You Don’t Need to Be a Sailor to Start Sailing

We started with zero experience—and now we live full-time on our sailboat, exploring coastlines and calling the sea home. What we’ve learned is that sailing isn’t reserved for the wealthy or the born-and-raised-by-the-water crowd. It’s for anyone curious, adaptable, and willing to learn.

Start small. Get on boats. Learn from others. Whether your dream is a weekend on the bay or sailing around the world, the first step is simply deciding to begin.