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72 Hours in Waikiki: Jay Kitashima’s Local Guide

waikiki surfing

Looking to experience Waikiki like a local? Jay Kitashima, Halepuna Waikiki’s Director of Operations, shares his top spots and ways to embrace the island spirit over a perfect weekend.

 

Friday Evening – Sunset & Jazz

Check in at Halepuna, snap your first lanai photo, then head to House Without A Key for sunset cocktails, live Hawaiian music, and hula performances. Cap the night at Lewers Lounge with jazz-inspired cocktails and live music—charge it all to your room for ultimate ease.

Pro Tip: Stock up on local snacks at Foodland for your room.

 

Saturday Morning – Pastries & Surf

Fuel up at Halekulani Bakery with pastries like the classic Pabana Croissant and Lilikoi Meringue Tart or brand-new Mango Bread. Then hit the waves with a complimentary Art of Surfing demo or a private lesson with Gone Surfing Hawaii.

 

Saturday Afternoon – Culture & Coastline

Explore Hawaii’s art and history with Halepuna Access to the Honolulu Museum of Art or Bishop Museum. Take a scenic drive along Oahu’s coastline, stopping for lunch at Rainbow Drive-In or Side Street Inn, and don’t miss Waiola Shave Ice for a sweet treat. Relax back at Halepuna’s Vitality Pool and Sun Deck before sunset.

 

Saturday Evening – Sunset Sail & Dinner

Set sail with Sail Honu Hawaii for a breathtaking Waikiki sunset, then enjoy dinner at UMI by Vikram Garg in the Halepuna lobby, where island flavors meet global culinary inspiration.

 

Sunday – Yoga, Brunch & Shopping

Start with Mauka Yoga, then savor Sparkling Sunday Brunch at Orchids with ocean views, a carving station, seafood bar, and more. After checkout, explore Royal Hawaiian Center for local and luxury shopping, and grab an acai bowl from Island Vintage Coffee or a sweet from Penny’s Malasadas before heading home.

 

Experience Waikiki like a local with Halepuna as your home base—where every moment from sunrise to sunset is curated for discovery, relaxation, and island inspiration.

Halepuna Pool
Halepuna sunset
Honolulu Museum of Art
UMI by Vikram Garg mai tai pancake
aerial waikiki