Chasing Waves, Sunsets, and Perfect Mai Tais in Waikiki

Almost two decades had passed since I last set foot on any of the Hawaiian Islands—but last year, three unconnected trips took me back to Oahu, including two centered solely on Waikiki, where I developed an unexpected, albeit nostalgic, retro-hued appreciation for Honolulu’s most iconic neighborhood. Once the glamorous hub of postwar travel in the ’50s and ’60s, by the 1980s, Waikiki struggled with commercial excess. Today, that image has shifted, and a mindful revival is well underway—one that centers on Native Hawaiian culture, local stewardship, and a renewed sense of place. From surf and ukulele lessons to museum hopping and hiking Diamond Head, Waikiki and its environs offered plenty of ways to craft the perfect island weekend—and with Hawaiian Airlines now offering nonstop flights from cities including Boston, Austin, and Salt Lake, this iconic side of Oʻahu is more accessible than ever for travelers beyond the West Coast.

“The best way to show love and Aloha in Hawaii is to give someone a lei and let them know they’re special,” Aunty Macky shared during a workshop inside the Royal Hawaiian Center in downtown Waikiki. Seats for her class on Friday mornings fill up quickly with the meditative process – using a long needle to link vibrant pink orchids, fragrant white tuberose, and marigold flowers – trickier than it looks. She explained how each flower represents an element of life, with the garland’s increasing length symbolizing cherished moments. “Make sure you fill it with happiness,” she tells my group. One of several complimentary cultural experiences offered at the luxury retail and lifestyle hub, a private hula lesson led by Royal Hawaiian Cultural Director and master hula teacher Puake’ala Mann, who demonstrated basic hand gestures and footwork while sharing historical events honored by this storytelling dance, was another highlight.

A Fresh Perspective on an Iconic Destination

For a deeper dive into Hawaiian culture and history, I carved out time to visit ʻIolani Palace and the Bishop Museum. Stepping into the only official royal residence in the United States felt like being transported back in time, its meticulously restored interiors revealing a fascinating glimpse into the lives of Hawaii’s last reigning monarchs, King Kalākaua and his sister, Queen Liliʻuokalani. Founded in 1889 and home to the world’s most extensive collection of Hawaiian and Pacific artifacts, the Bishop Museum was impressive—drawn into stories of gods and ancient legends, I lingered longest on the first floor of its fabled Hawaiian Hall, although I was equally captivated to learn that the full-sized sperm whale model, suspended from the ceiling, has anchored the space for over a century.

Admission to both sites is complimentary at a handful of hotels across Honolulu, including Halepuna Waikiki by Halekulani, whose “For You, Everything” program also includes access to Doris Duke’s Shangri-La estate and Honolulu Museum of Art. There are myriad reasons to stay here. Secluded yet centrally located, it’s wonderfully tucked away, yet just steps from Kalākaua Avenue and Waikiki Beach. My room included a postcard-perfect Pacific Ocean view, and the eighth-floor infinity pool was a lovely place to unwind. Popping in next door for pastries (try the pabana croissant with lilikoi, mango, and banana crème) from Halekulani Bakery became a morning ritual. Dining at signature restaurant UMI by Vikram Garg was also exceptional.

Echoes of Old Hawai‘i and Waikīkī’s Gentle Revival

The true magic, however, might just lay in its connection to its sister property across the street: the legendary Halekulani Hotel, where catching the iconic sunset hula performance beneath its 135-year-old kiawe tree at House Without A Key and lingering over an after-dinner cocktail with live jazz at Lewers Lounge beautifully captured the spirit of old Hawai’i.

But no visit to Waikiki would be complete without time on the water. On its quiet southern side, I dusted off some rather rusty paddling and pop-up skills with a lesson at World Longboard Champion Kai Sallas’ Pro Surf School Hawaii, followed by brunch at beachfront restaurant Hau Tree inside the boutique Kaimana Hotel. Beyond the waves, and despite sharing the trail and summit with more people than I imagined at 7 in the morning (even with the non-Hawaiian resident reservation system), hiking Diamond Head was another quintessential “when in Waikiki” experience I didn’t regret–as much for the panoramic views of Honolulu and the coastline as chancing upon the vibrant KCC Farmers Market on my stroll back into town.

Another plus for staying at Halepuna Waikiki by Halekulani was its proximity to great shopping —namely inside the Royal Hawaiian Center, where I picked up an aloha shirt from Kahala (founded in Honolulu in 1936, it’s the oldest operating apparel company in Hawaii and regularly collaborates with local artists on special edition designs) and browsed Hawaii-made goods at House of Mana Up. Even the ever-present—and oversized—ABC Store on Lewers Street held charming finds. For a more contemporary take on Hawaiian culture, one afternoon I ventured just beyond Waikiki to SALT at Kaka’ako, an urban district imbued with the creative energy of modern Honolulu and home to indie boutiques, street art, and third-wave coffee shops.

When it came to cocktails, though—namely that quintessential Mai Tai—no place captured the spirit like the aptly titled Mai Tai Bar at The Royal Hawaiian. Set on the sand within the legendary “Pink Palace of the Pacific,” it was easy to picture travelers savoring the same views of Diamond Head that have enchanted visitors since the early 1900s.