A Windbag Warmup – Waialeʻe to Haleʻiwa

Story by Terry Shimabukuro

Photos and video as credited

July 19, 2026

Half of the kayakers on this paddle had survived a “hairy” journey around Kahuku Point in Small Craft Advisory wind and swell the previous week. As we gathered at Waialeʻe we watched close to SCA level whipping up white caps just offshore. Leader Stan D., one of the Kahuku Point survivors, was more cautious than normal in his pre-launch briefing and had us all buddy up. But, unlike the previous week where more than half the paddle was either into a strong headwind or starboard-side wind we knew that we’d have a tailwind the entire run so we were confident that this would be a much more enjoyable paddle…and what a joy it was!

Sunset Beach from about half a mile offshore — No surf so Sunset Beach was quiet – *photo by Terry*

The four of us that brought sails for this journey were treated to perfect conditions for a Windbag warmup. I flew down the coast with my Wind Paddle pop-up sail. According to my tracker I hit a max speed of 8 mph with an average over 5 mph. My heart raced when I’d catch a trade swell and throw rooster tails off both sides of my hull. Most fun that I’ve ever had kayak sailing!

Stan loaned his Wind Paddle to Debi and she became an instant sailing enthusiast. Stan coached Debi and Sandy in the finer points of handling a pop-up sail as he paddled hard to keep up with them.

Looking through the viewport of a red kayak pop-up sail — The view through Sandy’s sail – *photo by Sandy*

Kayaker with a yellow sail crossing in front of the Waimea Bay beach — Sailor Steve cruising across Waimea Bay – *photo by Terry*

With no north swell we coasted easily onto the beach at Waimea Bay for a short lunch break. Daring youngsters entertained us with their rock diving. Their exuberant energy spurred Steve and Stan to take Debi spelunking into the caverns under the rock and at the end of the beach.

Eight kayaks on the beach at Waimea Bay — Kayaks parked for our lunch break – photo by Debi

A big splash from a jumper off of the Waimea Bay jumping rock with lots of people on standing on the top of the rock — The famous jumping rock – photo by Sandy

Man and woman in the water in the cavern under the jumping rock — Steve and Debi spelunking – *photo by Sandy*

Man crawling into a sand filled cavern with a very low ceiling — Steve puts his best side forward – *photo by Sandy*

Woman looking into a sand filled cavern from the open end of the cavern — Howzit Debi! – *photo by Sandy*

The wind had calmed down a bit after lunch, but it was still strong enough for us to continue sailing all the way back to Haleʻiwa. Smooth sailing, no drama, just FUN!

Three kayakers paddling with Kaʻena Point on the horizon — Stan, Doug and Bill leave Waimea for Haleʻiwa – *photo by Terry*

Video by Terry and Sandy