Blog

Insights and updates from Tradewinds School

Flipping the Script: AI That Asks Questions Instead of Giving Answers

By Andy Szybalski • February 10, 2026

Most people think AI in education means AI that answers questions. What if we flipped the script? At Tradewinds, we're building AI that makes students think harder, not smarter.

Watch: Our Admissions Info Session with Head of School Carl Sabatino

By Andy Szybalski • February 9, 2026

Head of School Carl Sabatino walks through Tradewinds School's educational philosophy, curriculum framework, and admissions process in this 53-minute recorded presentation.

A Successful Info Session and an Invitation to Join Us This Sunday

By Andy Szybalski • January 22, 2026

Yesterday's Admissions Info Session was a success, with great conversations about gifted education in Hawaiʻi. If you missed it, the recording will be sent out soon. Meanwhile, join us this Sunday at the Hawaii K-12 Parent & School Expo at Bishop Museum.

Financial Aid Applications Now Open for Fall 2026

By Andy Szybalski • January 20, 2026

We're excited to share that financial aid applications are now open for families applying to Tradewinds School. Applications are open for grades K–5 and reviewed on a rolling basis.

Campus Transformation Underway: A Sneak Peek at Our New Learning Spaces

By Andy Szybalski • January 18, 2026

Demolition started yesterday at our new 1041 10th Avenue campus. What was once a traditional classroom building is now on its way to becoming something entirely different: a learning environment designed from the ground up to support deep, student-driven work.

We've Secured Our Campus in Kaimukī

By Andy Szybalski • January 16, 2026

I've been waiting for weeks for the moment when I could share this news: we've secured our campus! Tradewinds School will be located at 1041 10th Avenue in Kaimukī.

Future City Design Class + January Info Session Details

By Andy Szybalski • January 9, 2026

Last-chance learning opportunity: Future City Design from Cresconova Global Courses, plus a reminder about our January 21 Admissions Info Session at Treehouse Coworking in Kahala.

Now Accepting Kindergarten Applications + Online Assessment Booking

By • January 8, 2026

Two updates for families considering Tradewinds for Fall 2026: we are now accepting kindergarten applications, and online booking for cognitive assessments is available.

Cognitive Assessment: What Families Need to Know

By Andy Szybalski • January 1, 2026

A cognitive assessment is a required part of the Tradewinds admissions process. Here's what families need to know about the WISC-V, how to find a provider, and why these assessments matter for understanding your child's learning profile.

January Admissions Info Session: Understanding Gifted Education

By Andy Szybalski • December 19, 2025

Join us January 21 for a conversation with Head of School Carl Sabatino about what gifted education actually looks like. We'll explore the difference between 'schoolhouse gifted' and gifted, and whether Tradewinds might be the right fit for your family.