Roberta Oaks, Photo by Jennifer Brotchie

Fashion designer Roberta Oaks grew up in Missouri but has called Honolulu home for the last 13 years. Credited with modernizing the Aloha shirt, Oaks sells her designs at her namesake boutique in the heart of Chinatown. When she’s not presiding over her lifestyle brand, you’ll find her at one for these Oahu spots.

Hiking trail

“Kuliouou Ridge Trail [just outside Honolulu] has 360-degree views of the whole island. It’s perfect for families because it’s challenging, but not dangerous. It takes a non-hiker four hours round-trip, but, if you’re skilled, it’s half that time. It’s a great workout that has the benefit of amazing views.”

Happy hour

“No matter where you go in Honolulu, there seems to be a happy hour somewhere. I love the one at Mahina & Sun’s inside the Surfjack, a retro-style boutique hotel. It has a pizza-and-two-local-beer happy hour for $20. It’s a hidden gem in Waikiki that’s a total locals’ hangout.”

Chinatown gems

“Architecturally, Chinatown is unique, and it’s the only neighbourhood on the island where all the businesses are locally owned and operated. Jewelry designer Ginger13 is well-curated, and Barrio Vintage has vintage Hawaiian clothing. Owens & Co. is a good place for gifts. Encore Saloon is a taco bar, and they have a slushy machine that makes margaritas with in-season fruit.”

Day trip

“Waimea Bay on the North Shore is hard to beat. In summer it’s as flat as a lake, crystal-clear and you can see turtles.”

Coffee shop

The Manifest is a coffee shop by day, cocktail bar by night. I’m a die-hard mocha fan, and the Avocado Toast at their Toast Bar is always yummy, too.”

Live music

The Republik is a great venue for shows from the mainland. Anything cool that’s happening is there. It’s a small venue, but it has an indie rock show vibe. Then there’s Downbeat Lounge, a small punk bar, which is also a good spot to catch local bands.”

Getting there: WestJet flies to Honolulu twice a day from Vancouver.