20 Things I wish I knew Before Cruising on a Sailboat

You can watch every YouTube video and read every forum, but some of the most important sailing lessons are the ones nobody talks about—the ones you learn the hard way.

In this video, I'm sharing 20 things I truly wish someone had told me before I started cruising on a sailboat. This isn't textbook theory; this is the real-world, practical advice that can save you time, money, and a whole lot of stress out on the water.

From the surprising truth about sailing licenses and the importance of a good solar setup, to why your anchor is your most critical piece of gear and the simple fact that you'll motor more than you think, these are the lessons that make the difference between struggling and thriving.

00:00 - Intro
00:52 - Learn to reef early and often
01:43 - Dinghies should be easy to deploy
02:36 - Sailing licenses don’t actually teach you how to sail
03:33 - The best sailors are calm and adaptable
04:29 - Good solar and battery systems bring freedom
05:24 - Prioritize fixing functional systems before aesthetics
06:26 - Waves and wind are not the same thing
07:27 - No one cares what your boat looks like
08:28 - Your anchor is your most important piece of gear
09:28 - A windlass isn’t a luxury—it’s a necessity
10:14 - Things always break—bring spares and tools
11:15 - The dinghy is your car
12:18 - Inboard diesel engines are worth their weight in gold
13:18 - Don’t only prepare for heavy weather
14:19 - Start small and go now
15:20 - Osmosis won’t sink your boat
16:24 - Where can I anchor?
17:28 - Running rigging can be washed in a washing machine
18:28 - Docking and anchoring well is more important than sailing well
19:36 - You’ll motor a lot more than you expect
20:38 - Ending

If you're dreaming of casting off the lines, this is the honest, no-nonsense guide you need to hear.

What's the one thing YOU wish you knew before you started sailing? Share your hard-earned lesson in the comments below!

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