Are you dreaming of learning how to sail? Sailing is an AMAZING platform for adventure, discovery and exploration!
Perhaps you’ve been watching sailing video blogs of couples and families sailing around the world and wonder if this could be you?
If you are reading this, you’re probably thinking something along the lines of:
“I would love to learn to sail… but how do I even start?“
“Is it too late for me to learn to sail?“
“Can I actually become competent and captain a sailboat?“
YES, YOU CAN LEARN TO SAIL AND EMBARK ON SAILING ADVENTURES OF YOUR OWN!
This guide will give you a roadmap of how to confidently embark on your own sailing journey and covers:
Here’s the uncomfortable truth:
Sailing is not hard, but becoming independently capable is a journey.
You can take a course, pass your certifications and log a few days on the water and still not be ready to charter a boat or buy your own boat and cast off the dock lines.
This gap is where most beginners get stuck. The first step is to clearly define your goals, have realistic expectations and know the roadmap you need to take.

Over the years, we’ve found that most folks fall into one of three categories.
This is the LOWEST COMMITMENT and LOWEST SKILL REQUIREMENT TO LEARN TO SAIL
Requires real, applied skill, knowledge, certifications and experience
Requires layered competence over time, in a variety of vessels, locations and conditions
If your goal is #2 or #3, you need to approach your sailing training differently. Your journey from newbie to confident sailor will require more time on the water, more training and a more in depth roadmap to meet your goals. Most beginners underestimate this.

Sailing isn’t one skill. It’s a complex web of knowledge and skills. The first step is to gain the knowledge, skills and certifications that will give you a license to learn to sail. Once you have your license, you can then dive into opportunities to deepen all you know.
To become competent you first need knowledge and working ability in:
Most courses will teach you pieces of this, but few go through in an in depth, systematic fashion! Very few courses will insure you have a solid foundation when you learn to sail.

There are three main ways to learn to sail. Each has it’s trade offs.
LOCAL/DAY SAILING SCHOOL | LIVEABOARD COURSES | DIY LEARNING (BUY A BOAT AND GO) | |
| FORMAT | – Day at a time on the water, typically on weekends – Can go home each night | – 7 days living on a – boat sailing in international waters – Full immersion – Small groups | – Learn by doing – Informal Mentorship |
| PROS | – Lower cost – Convenient – Good, basic introduction and exposure to sailing and boats | – Continuous learning (not just class hours) – Real world conditions – Rapid skill development – Decision making exposure | – Flexible – Real World exposure |
| CONS | – Limited immersion – Minimal deep experience as you are typically in sheltered, coastal waters – Can take 6 months to a year to get through basic certifications – Typically not enough for competence | – Higher up front cost – Intense learning curve – Requires time to prepare for the course (studying materials) | – High risk of knowledge gaps – Slower progress – Potentially expensive mistakes |
If you are planning to learn to sail and charter boats internationally or your goal is to become a world cruiser on your own boat, you will need formal sailing certifications. All the major charter companies now require that you have sailing certifications, which confirm you have gone through a rigorous, structured training program and have the necessary skills and experience to meet insurance requirements to learn to sail and charter vessels.
In the same way, to obtain insurance for a private vessel, more and more insurance companies want to see formal sailing certifications or they may require that you have a paid, professional captain onboard your vessel.
Many countries have their own formal sailing certification entity. In the United States, it’s American Sailing and US Sailing, in Canada it’s the Canadian Yachting Association (CYA) and in England it’s the Royal Yachting Association (RYA)
Two of the most respected entities globally for most charter companies and insurance providers are American Sailing and the RYA.

| AMERICAN SAILING | ROYAL YACHTING ASSOCIATION (RYA) |
| Modular: Basic Keelboat Sailing – ASA 101, Basic Coastal Cruising ASA 103, Bareboat Charter ASA 104 and Cruising Catamaran ASA 114). These four certifications for the basis for doing international charters | More hierarchical: Competent Crew, Day Skipper, Coastal Skipper, Yachtmaster Coastal, Yachtmaster Offshore and Yachtmaster Ocean |
| Common in US and Caribbean | Strong international learn to sail reputation |
| Focused more on recreational sailors | More formal and rigorous training |
| Can be completed in a 7 day live aboard learn to sail course | Industry standard for professional mariners |
| Courses to charter can take 6-8 months to complete |
Which certification is right for you? It depends entirely on your personal goals! If you are a recreational sailor wanting to do charters or plan on buying your own boat, the American Sailing courses are a great foundation and the fastest path to start chartering. However, if you are desiring a much more rigorous program and may want to work commercially in sailing, then the RYA certifications may be more appropriate.
If your goal is competence, your training should include:
If your courses doesn’t include all these you may be getting EXPOSURE and not SKILL BUILDING OPPORTUNITIES!
Here’s the honest answer:
| BASIC FAMILIARITY | 2-5 Days |
| FUNCTIONAL COMPETENCE | 5-10 Days |
| TRUE COMPETENCE | 6 Months – 2 Years |
THE FASTEST PATH MOST ADULTS TAKE: An intensive week long live aboard course followed by independent experience on flotillas, offshore trips and charters.

The school and course you choose will depend on your personal sailing goals! There is no once size fits all approach.
Some of the key things to look at when choosing a sailing school:

Learning to sail can be an amazing experience and open up some incredible opportunities! However, you need to be clear about your own goals, and then craft a path that will help you achieve those dreams. Do you want exposure or competence? Do you want to sail occasionally or be able to charter and captain your own vessel? You can go from newbie to confident captain if you choose immersive training and learn to sail with hands-on responsibility in real-world conditions, and then follow up with opportunities to practice on your own.









With Nautilus, your liveaboard course is just the beginning of your sailing journey!
We're here to offer next step opportunities to deepen your sailing knowledge, skills and experience.
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