Halepuna Waikiki’s Jay Kitashima Shares His Ideal Three-Day Itinerary
At the heart of Waikīkī, you’ll find Halepuna Waikiki by Halekulani – a serene escape designed for travelers seeking luxury and award-winning hospitality. Behind its smooth operations and standout service is Jay Kitashima, the hotel’s Director of Operations, an O‘ahu local who brings a lifetime of local perspective to every guest’s experience.
Kitashima’s love for the land, culture, and community of Oʻahu is woven into his personal and professional life. After spending several years living in Las Vegas and Utah, he returned home with a renewed appreciation for Hawai‘i’s unique way of life. “Growing up, our family loved going to the beach and enjoying the surf around the island,” Kitashima said. “Back then, I didn’t know Hawai‘i was home to some of the most beautiful beaches and the best surf in the world. Today, I don’t take that for granted. I now surf with my kids as often as possible.”
That reverence for home and the joy of sharing it with others is central to Kitashima’s role at Halepuna. He believes that what truly sets the experience apart is the intentionality of the people behind the scenes. For him, sharing Hawai‘i’s magic with guests is more than a job. It’s a way to give back to the place that raised him.“Hawai‘i’s year-round perfect weather makes it a top destination,” he said. “You can surf in the summer and winter and golf any day of the week. Above all, though, Hawaiʻi’s people and culture truly are the reasons why this place is loved by so many.”
Three Relaxing Days in Waikīkī with Halepuna Waikiki as Your Hub
For travelers wanting to experience Waikīkī like a local, Jay Kitashima, Director of Operations at Halepuna Waikiki, shares his top must-visit spots and favorite ways to embrace the island spirit while maintaining some much-needed rest and relaxation. From Hawaiian cultural history to sunset sailing, here is his curated guide to the perfect escape along Oahu’s South Shore.
Day-by-Day Itinerary
Day 1: Dinner and Drinks
Check into Halepuna Waikiki by Halekulani
Evening: Sunset Sips, Fresh Island Flavors, and Live Jazz
Day 2: Outdoor Adventures and Cultural History
Morning: Pastries First, Paddle Later
- Start the day with a stop at Halekulani Bakery, known for its wide selection of sweet and savory pastries, freshly brewed Kona coffee, and island-inspired treats. Travelers recommend the Pabana Croissant, Big Island Macadamia Nut Chocolate Croissant, and Lilikoi Meringue Tart, all crafted by pastry chef Michelle Baldomero, who has been with Halekulani for 26 years.
- After breakfast, channel your inner surfer with a complimentary demo through the Art of Surfing, learning the basics of paddling and wave etiquette against the stunning backdrop of Waikīkī Beach. For a more personalized experience, get a beginners surf lesson, where seasoned instructors guide guests through everything from their first pop-up to mastering the perfect ride.
Afternoon: Arts and Island Culture
- Enjoy Hawaiʻi’s history and culture with Halepuna Access, a hotel program offering complimentary admission to the Honolulu Museum of Art or Bishop Museum. If you want to venture further, rent a car, cruise along Oʻahu’s stunning coastline, and ask the Halepuna guest relations team for the best routes and scenic stops.
- Refuel with a stop at either Rainbow Drive-In for a classic plate lunch or Side Street Inn for family-size portions of local comfort food. For a sweet, nostalgic treat, Waiola Shave Ice offers the perfect taste of a local Hawaiʻi tradition.
- After your adventure, return to Halepuna to unwind at the Vitality Pool and Sun Deck, where sunshine and cocktails await.
Evening: Sunset Sail and Fine Dining
Enjoy a breathtaking sunset from the sea with local small business Sail Honu Hawaii. Travelers rave about the hospitable and knowledgeable staff and the gorgeous views.
Afterwards, savor a refined dinner at UMI by Vikram Garg, conveniently located in the Halepuna lobby. Chef Garg masterfully blends island flavors with global influences, creating dishes celebrating Hawaiʻi’s freshest ingredients.
Day 3: Brunch and Browsing
Morning: Stretch and Savor
Start the final day with a complimentary yoga class in The Garden, on Halepuna’s 8th floor. Afterward, recharge with Halepuna’s Sparkling Sunday Brunch at Orchids, where stunning ocean views and an impressive lineup of offerings such as the seafood bar, carving station, and ice cream sundae bar set the stage for a perfect farewell.
Afternoon: Royal Hawaiian Center & Departure
After checking out, store your suitcase with Halepuna and walk to Royal Hawaiian Center, Waikīkī’s premier retail, culinary, and cultural destination. Explore over 90 shops, where guests can find everything from classic Aloha shirts by Kahala to luxury goods at flagship stores like Hermès, Fendi, and Saint Laurent. Thanks to low local taxes and regional pricing, it’s a smart stop for fashion lovers, especially with cult favorites like Stüssy, KITH, and Yumi Kim in the mix.
Finally, before heading home, grab an acai bowl from Island Vintage Coffee or a famous treat from Penny’s Malasadas for the road – a delicious way to savor the island one last time.
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