Am I Ready for the Intermediate Bareboat Sailing Course?
- Episode 081 Your Pocket Sailing Instructor podcast
- Released: January 5, 2026
- Duration: 21 min 45 sec
“Before you step aboard for an intermediate course, make sure your skills, experience and expectations are ready too.” ~ Sailing According to Coach Penny
Wondering whether you are ready to move beyond basic sailing and take an intermediate live-aboard cruising course? I walk you through the experience, knowledge and preparation that will help you get the most from the course. I discuss prerequisites, prior sailing time, navigation skills, crew management, provisioning and the shift toward making real-time decisions aboard. The episode is less about checking boxes and more about honestly assessing whether you have enough foundation to take on greater responsibility. If an intermediate bareboat cruising course is on your horizon, this episode will help you identify what to practice before you arrive and what to expect once you are there.
WHAT YOU’LL LEARN
- Identify skills to practice before a live-aboard course
- Assess whether your sailing experience is sufficient for an intermediate course
- Understand the importance of practical navigation skills
- Prepare for greater responsibility in crew and boat management
The Intermediate Cruising course is where sailing starts to feel much more like real-world cruising. Rather than heading out for a day sail and returning to the same dock, you are living aboard the boat, travelling through unfamiliar waters and taking responsibility for the day-to-day decisions involved in getting yourself, your crew and your boat safely from one destination to the next. For many sailors, this is an important step toward being able to confidently charter a bareboat or cruise independently on their own boat.
A big part of that experience is learning how to plan where you’re going and where you’re going to spend the night. You may need to evaluate an anchorage based on the forecast, wind direction, depth, bottom conditions, protection and swinging room, then decide whether it is still a good choice when you actually arrive. Other nights might mean finding a marina, figuring out whether there is space available, approaching an unfamiliar dock and adapting your docking plan to the wind, current and configuration of the marina. You may also encounter mooring buoys or situations where you need to secure the boat using a combination of an anchor and lines ashore. These are exactly the kinds of situations you’ll encounter when bareboat cruising somewhere new.
You also begin learning what it really means to manage the boat while you’re away from home base. Fuel and water become resources you need to think about. Batteries need to be monitored. The head, holding tank, refrigeration, galley and electrical systems all need to keep working. You’ll perform routine engine checks and maintenance and learn some basic troubleshooting for problems such as an engine that won’t start, overheating or cooling water that isn’t flowing properly. You also need to think about provisioning, spare parts, tools, first-aid supplies and what you might reasonably need if something goes wrong when you’re several hours – or several days – away from your home marina.
Navigation and passage planning also become much more meaningful because you’re actually using them to get somewhere. You’ll work with charts, weather forecasts, aids to navigation, position fixing, courses, distances and estimated arrival times while making real passages. Instead of navigation being an exercise at a chart table, you’re using that information to answer practical questions: When should we leave? How long will this passage take? What will the weather be doing when we arrive? Where is our backup destination if conditions change? Do we have enough daylight?
This is also where you begin to experience what bareboat cruising is really about: putting all of your individual sailing skills together. Sailing the boat is only one part of being the skipper. You are also looking after your crew, monitoring weather, managing the boat’s systems, choosing safe destinations, making docking and anchoring decisions, preparing meals, conserving resources and changing the plan when circumstances require it. The goal isn’t simply to demonstrate individual maneuvers – it’s to become comfortable taking responsibility for the whole cruising experience.
That’s why I think Intermediate Cruising can be such an important step between knowing how to sail and genuinely feeling ready to take command of a boat for several days on your own. If bareboat chartering, multi-day coastal cruising or eventually owning and cruising your own boat is one of your goals, these are exactly the skills and experiences you’ll want to start developing.
Cheers!
If you enjoyed this episode, you’ll love these too!
- Episode 071: How to build experience between courses
- Episode 087: You’ve taken your course, now what?
- Episode 038: Why you still don’t feel confident sailing
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About Penny Caldwell
Penny Caldwell is a Canadian sailing educator, Sail Canada Instructor Evaluator, marine consultant, and host of the Your Pocket Sailing Instructor podcast. With nearly three decades of teaching experience, she is passionate about helping sailors of all skill levels build confidence, develop practical seamanship skills, and enjoy a lifetime on the water. Through her articles, podcast, instructor development programs, consulting, and sailing adventures, Penny shares real-world knowledge that makes sailing safer, more enjoyable, and more accessible for everyone.
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Sailing is a lifelong learning journey, and some of the best ideas come from fellow sailors. Have a question about this topic, or a tip you’d like to share? Leave a comment below—I read every one and enjoy hearing about your experiences on the water!
