New Sailor Sailing Gear – Do I REALLY Need That?!

“Do not build your sailing kit all at once. Start with what you already own, get on the water, and let your actual sailing tell you what is worth upgrading.” ~ Sailing According to Coach Penny

When you first get into sailing, it is very easy to believe you need an entire closet of specialized gear before you can even step onto a boat. Sailing stores are full of wonderful things, and I love good gear as much as the next sailor, but most beginners really do not need to buy everything at once. My advice is to start with the basics, get some time on the water, and let your own sailing tell you what you actually need.

What You’ll Learn

  • What gear you actually need to start sailing
  • Which items can wait until you have more experience
  • How to choose practical clothing, footwear and a PFD

For most new sailors, I would focus first on practical clothing and footwear. You want non-marking shoes with decent grip, clothing you can move comfortably in, sun protection, and layers that make sense for your local weather. A pair of gloves can be useful if you are handling lines regularly, but even those are not necessarily essential for your first outing. If you are taking a course, ask the school what safety equipment is supplied before buying your own.

One of the biggest mistakes I see is people buying expensive technical equipment before they know what kind of sailing they enjoy. Day sailing on a warm inland lake has very different gear requirements from offshore sailing on the West Coast. The same goes for things such as foul weather gear, inflatable PFDs, sailing boots, knives, watches and navigation gadgets. They may eventually be excellent investments, but they do not all need to be day-one purchases.

I also encourage new sailors to borrow, rent and try gear whenever possible. Pay attention to what experienced sailors around you use and, more importantly, why they use it. After a few days on the water you will quickly discover which items make you more comfortable, safer or more efficient—and which ones simply take up space in your sailing bag.

Sailing does not have to be an expensive sport to enter. Start simple, spend your money thoughtfully and build your kit as your skills and adventures grow. The best piece of sailing equipment you can invest in at the beginning is still knowledge and time on the water.

Cheers!

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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—and nine seasons spent building and running the successful sailing school Sail Nelson—she has dedicated much of her career to helping people become safer, more capable, and more confident sailors.

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 practical, 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!

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