Sails – Finding a Sailmaker
- Episode 061 Your Pocket Sailing Instructor podcast
- Series: Sails Series
- Released: November 2, 2023
- Duration: 26 min 0 sec
“Because the “best” sail isn’t necessarily the most expensive one — it’s the one that’s right for your boat and the way you sail.” ~ Sailing According to Coach Penny
Buying new sails is a significant investment, and choosing the right sailmaker can make an enormous difference in the final result.
In Part 3 of my Sails Series, I talk about my own experience researching and selecting a sailmaker, including the process I went through when ordering new sails for Spindrift. We’ll look at why price shouldn’t be your only consideration and why a good sailmaker should spend some time understanding you, your boat and the type of sailing you actually plan to do.
WHAT YOU’LL LEARN
- Why choosing the right sailmaker matters
- What to consider before requesting sail quotes
- Questions to ask a prospective sailmaker
- Why your sailing goals should influence your sail choice
- How to compare sail quotes more effectively
- Why the cheapest quote isn’t necessarily the best value
- The importance of communication throughout the process
- What I learned while researching sails for Spindrift
Buying a new sail isn’t something most recreational sailors do very often. That’s part of what makes the process difficult. You may be spending thousands of dollars on something you haven’t purchased before — and you’re suddenly faced with terminology, materials, construction methods and options that can make comparing quotes surprisingly complicated.
When I went through the process of ordering a new headsail for Spindrift in 2018, I did a lot of research. Later, when it was time for a new mainsail in 2021, I had the benefit of that previous experience. One of the biggest lessons was that choosing a sailmaker is about much more than simply sending out a few requests and choosing the lowest number.
A good sailmaker should want to know how you use your boat. Are you racing? Day sailing? Coastal cruising? Planning longer passages? Are you looking for maximum performance, or is durability and easy handling more important? There isn’t one perfect sail specification for every sailor, which is why those conversations matter.
It’s also important to make sure you’re comparing apples to apples when you receive quotes. Fabric, weight, construction, hardware, reef points, UV protection and other details can all affect the final price. A cheaper sail may simply be a very different sail. Ask questions until you understand exactly what you’re being quoted.
Finding the right sailmaker should feel a little like building a relationship. You’re relying on their expertise to translate your boat, budget and sailing goals into a sail that works for you. Take your time, do your homework and don’t be afraid to ask lots of questions before handing over your deposit.
Cheers!

If you enjoyed this episode, you’ll love these too!
- Episode 059: Sails – Damage Prevention & Basic Maintenance
- Episode 060: Sails – DIY Repairs
- Episode 072: Standing Rigging 101: What to Check Before It Fails
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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!
