Since day one, we’ve filled this website with hundreds of tips and videos to help you build your skills. We ran the Think Like A Blockhead Contest to see what kind of advice you would give to other Blockheads.

Here’s what you had to say…

My coach always says “Anticipate,” so I think that predicting the shifts and the fleet is the best way to do well in dinghy sailing. I also think that using your time on the water wisely is really important. – Andrew Chisholm



Low-Density Starts — Have a clean start on the clean end of the line so you can do what you want. Something my dad taught me! – Cadance Oswald



Always arrive early for practices and regattas. Why? Because it gives me plenty of time to rig, make lunch, visualize the racing day, and help my teammates. – Cal King



Always clean and wax your boat. A clean boat is a fast boat. – Caleb Kinnear



Two pieces of advice: 1. Fix it RIGHT the FIRST time, so you don’t have to fix it again. 2. McLube it or lose it! – Grayson Rosenberg



Just send it! – Natasha Macklin



My coaches taught me to always take care of my boat. If I know how to maintain and fix my boat then if something bad happens on the water I can fix it and keep racing! – Quinn ODell



2 eyes. 2 ears. 1 mouth. (If you open your eyes close your mouth and listen you’ll learn a lot more.) – Sam Rosenbaum



At Cambridge Yacht Club Jr. Sailing School over the summer, my instructor always told me to look around, not just at my boat. – Sean Welker



It’s not about winning individual races. It’s about being consistent over the long run. – Will Burkhart


We randomly selected a winner out of all of the entries, and Cal King won the fabulous prize package! Congratulations, Cal!



March Trivia Contest

The deadline to enter is April 30, 2024. With the correct answer, you could be the one lucky


First Blockhead to the Island 2023

Calling all Blockheads! The Chicago Yacht Club Race to Mackinac® is a legendary race — 289.4 nautical miles


First Blockhead to the Island

Megan Geith is the ‘First Blockhead To The Island’ in the 2022 Chicago Yacht Club Race to Mackinac®!


Will You Be the First Blockhead to the Island?

Calling all Blockheads! The Chicago Yacht Club Race to Mackinac is a legendary race — 289.4 nautical miles

What exactly is a Blockhead? If you are totally obsessed with how to rig and sail your boat, you might already be one! Join the community of Blockheads to learn more about the sport, engage with others and share sailing experiences. This site serves as the hub for Blockheads globally, where you can discover how to join, media, tips and tricks, contests, and events. This program is all about YOU and we want to hear from everyone! Not seeing something? Your feedback is crucial, feel free to shoot us a comment or message.