Whether inspired by the new Lilo & Stitch remake or simply seeking a destination that feels far-flung yet close to home, Hawaii offers travelers the perfect escape with no passport required. For those wanting to experience Waikiki 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. From hidden gems to classic Hawaiian experiences, here is his curated guide to the perfect weekend along Oahu’s South Shore.
Friday Evening – Sunset Sips, Fresh Island Flavors and Live Jazz 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 welcome for the hula show, reservations recommended for dinner.) Some of my go-to dishes from Chef de Cuisine Jarrin Otake include the Ahi Tataki and the brand-new Tutu Ma Asian Braised Short Rib, a nostalgic nod to his childhood in Waialua. Later, slip into the intimate setting of Lewers Lounge, where guests can find jazz-inspired cocktails like ‘That Was My Heart’ (Ella Fitzgerald), a tropical take on the classic Negroni, served alongside live sets from renowned jazz artists. It’s the perfect way for guests to end their first night in Waikiki, with the convenience of charging everything back to their room.
Pro tip: Make a stop at Foodland, a one-stop shop for everything and perfect for stocking the mini-fridge with snacks! Be sure to try their variety of poke, musubis, and other local favorites.
Saturday Morning – Pastries First, Paddle Later Start the day with a stop at Halekulani Bakery, known for its in-house baked pastries, freshly brewed Kona coffee, and island-inspired treats. My personal favorites include 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. As a special Saturday treat, guests can enjoy 10% off at the bakery by simply showing their room key, part of Halepuna’s Sunshine Perks program running now through August 31. After breakfast, guests can channel their inner surfer with a complimentary beach demo through the Art of Surfing, learning the basics of paddling and wave etiquette against the stunning backdrop of Waikiki Beach. For a more personalized experience, the concierge can arrange a private lesson with partner Gone Surfing Hawaii, where seasoned instructors guide guests through everything from their first pop-up to mastering the perfect ride, making it a truly unforgettable way to connect with the ocean.
Saturday Afternoon – Discover the Arts and Island Culture Enjoy a dose of Hawaii history and culture with Halepuna Access, a program offering complimentary admission to the Honolulu Museum of Art or Bishop Museum. Looking to venture further? Rent a Tesla and cruise along Oahu’s stunning coastline. Just ask the guest relations team for the best routes and scenic stops along the way. For a satisfying lunch, a stop at Rainbow Drive-In (mixed plate is my favorite) or Side Street Inn is a must. For a sweet afternoon treat, Waiola Shave Ice is the perfect choice. After the adventure, unwind at the Vitality Pool and Sun Deck, where the afternoon sun awaits and sunscreen, cocktails are always within reach.
Saturday Evening – Sunset Sail and Dinner at UMI by Vikram Garg Begin the evening with a group catamaran sail from Gray’s Beach or a private cruise with local small business Sail Honu Hawaii and enjoy a breathtaking Waikiki sunset from the water. 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 that celebrate Hawaii’s freshest ingredients and showcase his distinctive culinary vision.
Sunday Morning – Stretch and Savor Start the final day with a Mauka Yoga class in The Garden, Sunday’s Sunshine Perk. Afterward, recharge with Sparkling Sunday Brunch at Orchids, where stunning ocean views and an impressive lineup of offerings like the carving station, seafood bar and ice cream sundae bar to set the stage for a perfect farewell to Waikiki. (For more brunch inspiration, check out the latest Halekulani blog post: A Guide to Hawaii’s Best Brunch).
Sunday Afternoon – Explore Royal Hawaiian Center After checking out, store your suitcase with Halepuna and walk over to Royal Hawaiian Center, Waikiki’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. With Hawai‘i’s relatively low General Excise Tax (GET) on luxury goods (4–4.5%) and region-specific pricing, the Center is a savvy destination for luxury shoppers. Royal Hawaiian Center also hosts cult-favorite brands such as the Honolulu flagship Stussy, KITH, and Yumi Kim, appealing to fashion-forward visitors. For a light snack before heading home, grab a famous acai bowl from Island Vintage Coffee or a sweet treat from Penny’s Malasadas.
