A 3-Day Stay at Halepuna Waikiki
In 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.”
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
Today is all about settling into the hotel and going big for your first night on island.
Check into Halepuna Waikiki by Halekulani
Halepuna Waikiki. Photo by Brandon Barre.
Since its complete renovation in 2019, Halepuna has redefined boutique luxury in Waikīkī. All 288 guest rooms and public spaces were transformed entirely, allowing the hotel to reopen as Waikīkī’s first luxury boutique hotel. Lush interiors, impeccable service and a sense of calm elegance make it a favorite for travelers looking for a more intimate island stay.
Pro tip: Make a stop at Foodland Farms, a one-stop shop for everything, and perfect for stocking your hotel mini-fridge with snacks! Be sure to try their variety of poke, musubi, and other local favorites.
Sunset Dinner at House Without A Key
House Without a Key. Photo by Brandon Barre.
After checking in at Halepuna and capturing your first photo from the lanai, head across the street to House Without A Key for sunset cocktails. This iconic oceanfront restaurant at Halekulani sets the scene with live Hawaiian music, hula performances and stunning Diamond Head views. Walk-ins are welcome for the hula show, but reservations are highly recommended for dinner. Try the Ahi Tataki and the Tutu Ma Asian Braised Short Rib – a nostalgic nod to chef de cuisine Jarrin Otake’s childhood in Waialua.
- Address
- 2199 Kālia Rd #1936, Honolulu, HI 96815
Live Jazz and cocktails at Lewers Lounge
Lewers Lounge. Photo by Sarah Burchard.
Cap off your evening at Lewers Lounge listening to live sets from renowned jazz artists, while sipping on classic cocktails like Old Fashioneds and Negronis.
Day 2: Outdoor Adventures and Cultural History
Start the morning with world-class pastries and a surf lesson. Then dive into Hawaiʻi culture with a visit to Bishop Museum. Eat like a local for lunch and finish the day back on the water.
Halekulani Bakery
Pastries from Halekulani Bakery. Photo by Sarah Burchard.
Start the day with a stop at Halekulani Bakery, known for its wide selection of decadent 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.
Surf Lesson
Waikīkī Beach.
After breakfast, channel your inner surfer with a complimentary demo through Halekulani's 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.
Bishop Museum and Plate Lunch
Bishop Museum. Photo by Ben Ono / Hawaiʻi Tourism Authority.
Learn Hawaiʻi’s history and culture with a visit to Bishop Museum. Refuel with a stop at Rainbow Drive-In for a classic plate lunch. For a sweet treat, Waiola Shave Ice offers the perfect taste of a local Hawaiʻi tradition. Use a rideshare to get around or take TheBus.
Sunset Sail & Dinner
Waikīkī at sunset.
Wind down the day with a sunset cocktail sail. 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 Shopping
Before getting on that plane, treat yourself to a free yoga class at the hotel, Halekulani's famous Orchid's brunch and and afternoon of shopping.
Yoga and Brunch
Orchids. Photo by Brandon Barre.
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.
Shopping and a Snack at Royal Hawaiian Center
Acai Bowl. Photo by Sarah Burchard.
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. It's a fun stop for fashion lovers, especially with cult favorites like Stüssy, KITH and Yumi Kim in the mix. Before heading home, grab an acai bowl from Island Vintage Coffee.
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