In this feature, InStyle’s Senior Editor Diana Tsui (pictured below) documents what she packed and what she wore for her trip to Hawaii.

Having grown up in New York City, I’m lucky enough to have experienced the urban life. So when it comes to vacations, I go for the extreme opposite: Whether it’s snowboarding in Jackson Hole, Wyo., or hiking in upstate New York, I crave outdoor adventures. This time my husband and I headed to Oahu, Hawaii, with the intention of surfing, snorkeling, and indulging in all of the amazing local food.

Christopher Wu

When it comes to packing, I aim to squish the most amount of stuff into the tiniest bag possible and still leave room for snacks. I always bring back snacks from any locale. To maximize my tiny carry-on, the shoes go at the bottom. Then I roll up all my clothes and place them in by section—outdoorsy clothes go at the bottom and the lighter, more delicate pieces at the top.

Since we were headed to warmer climates, I brought three pairs of shoes: practical, if unattractive, hiking sneakers, my trusty Birkenstocks, and a pair of dressy (but low!) sandals for dinners out. Then I threw in some easy to wear silk dresses and separates—they pull double duty as coverups! A few bikinis, colorful sunglasses, and one rash guard later, I’m ready.

Click through the gallery to shop Diana’s stylish travel essentials!

—Diana Tsui; coordinated by InStyle’s Senior Market Editor/Digital Correspondent Dana Avidan-Cohn