Waikīkī has defined the Hawai‘i travel experience for generations, from before the days of ocean liners to beyond Boeing Dreamliners. And while reinventing itself every decade or so, Hawai‘i’s most popular destination also boasts a through-line of recognizing its deep Hawaiian roots. This fall is the perfect time to check out what makes Waikiki unique.
Celebrating a princess and Pride
Princess Ka‘iulani, the last heir apparent of the Kingdom of Hawai‘i, died at just 23 years old in 1899, but her memory remains cherished, especially by those in and around her former Waikīkī estate known as ‘Āinahau.
Its lush gardens exuded the fragrance of her signature flower, jasmine, and became home to strolling imported peacocks, which share their Hawaiian name with jasmine: pīkake. Although she left the estate as a young teenager for schooling in England, the princess returned as an advocate for Hawaiian sovereignty a couple years after the U.S.-backed overthrow of the monarchy in 1893. Princess Ka‘iulani died at ‘Āinahau, less than two months after becoming ill on a trip to Hawai‘i Island, reportedly prompting her beloved peacocks to shriek through the night, joining the human chorus of mourners.
In 1999, 100 years after her tragic passing, OUTRIGGER Resorts and Hotels erected a bronze sculpture of the princess on a tiny portion of her erstwhile home now known as Ka‘iulani Triangle Park, at the corner of Ka‘iulani and Kūhiō avenues. And every year since, the company has sponsored a celebration on her birthday.
This year’s commemoration takes place Friday, Oct. 16, from 5–9 p.m., beginning with a lei-draping of her statue by community groups and continuing with a celebration in the nearby OUTRIGGER Waikīkī Paradise Hotel lobby, which renowned florist Ocean Dreamer will have turned into a “paradise garden” worthy of the princess. Award-winning musicians Taimane and Ei Nei will perform along with island reggae artist Irie Love and former Hawai‘i poet laureate Kealoha, and shoppers can browse a curated marketplace and purchase food and drink.
Before and after the performances, Hawaiian Islands Stamp & Coin will offer a rare look at more than 75 items from Princess Ka‘iulani’s personal possessions or her life experiences, including one-of-a-kind artifacts such as 25 original photos (some personally autographed), her address book and handwritten letters, a favorite bracelet, a painting that she created, and her ‘ukulele.
“I grew up in Waikīkī and used to walk by her statue every day, and I used to surf where she used to surf,” notes Kiana Beimes, general manager of OUTRIGGER Waikīkī Paradise Hotel. “To honor the princess has been very meaningful to me. … I invite everyone to join us and honor her together.”
Honolulu Pride festival also returns to Waikīkī this year, kicking off with a Pau Hana party at International Market Place Oct. 14. Presented by the Hawaii LGBT Legacy Foundation, Pride features a concert headlined by Big Freedia at Hawai‘i Theater Oct. 15, the official opening party at Scarlet nightclub Oct. 16, and the Oct. 17 Pride parade along Kalākaua Avenue, which leads to a celebration at the Tom Moffat Waikiki Shell with four hours of live entertainment and 70 community booths. Other festivities in Waikīkī include an after-party, drag brunch, pool party and closing dance party; see the website for details.
Island-style indulgences
Whether you’re in the mood for a classic cocoa puff, a poi mochi doughnut or a liliko‘i malasada or a mac nut waffle, Liliha Bakery can hit the sweet spot — and offer plenty of savory options for breakfast, lunch and dinner, too, at its new Waikiki Beach Walk location, 226 Lewers St. The sixth and newest outpost in the locally owned chain, founded in 1950, is just a few blocks from another at Waikiki International Market Place. Both are open daily 7 a.m.–10 p.m.
Another local favorite, Side Street Inn, debuted a Waikiki Beach Walk branch in late September. The menu includes hearty dishes such as ‘alae salt edamame, pan-fried pork chops and garlic chicken popularized at the original hole-in-the-wall location in Ala Moana, a go-to since its opening in 1992. The new branch is open for dinner daily starting at 4 p.m., and from 11 a.m. on weekends; closing hours vary.
The Mediterranean also inspires island chefs — witness Botanico Waikiki, which has won several dining awards since its opening in October 2025 in Waikiki Shopping Plaza. Its four-course Terra e Mare (“Land and Sea”) menu highlights fresh local produce and seafood along with iconic Italian dishes such as tiramisu, pasta Bolognese and prosciutto with fruit; it’s $80, with an optional three-course wine pairing for $35.
Renovation rooted in history
Before Waikīkī’s contemporary era of bustling streets and beachgoers, the area was known for bubbling streams and springs — hence the meaning of its name, “spouting water.” Queen Emma (1836–1885) was among the ali‘i (chiefs and royalty) who had land and gardens here, including a residence she inherited from King Lunalilo after his death in 1874. In the early 20th century, Duke Kahanamoku and the Waikiki Beachboys helped put Waikīkī on the map as the birthplace of modern surf culture. In 1967, the OUTRIGGER Waikīkī Beach Resort opened on the site of the former Outrigger Canoe Club and in 1992 became home to Duke’s Waikiki, a restaurant inspired by the legendary waterman.
Now the resort has completed renovations of all 524 guest rooms and suites that pay tribute to that history, part of an ongoing $100 million metamorphosis of the first OUTRIGGER branded resort. Each room includes a custom mural of Queen Emma’s lily garden by Kamea Hadar, along with rugs reflecting the pattern of a retreating wave on sand and woven-basket screens that replaced walls to draw the eye to the ocean. In the corridors, graphic rivulets recall ʻĀpuakēhau Stream, which once flowed here, while room numbers feature surf images by renowned photographer Zak Noyle.
“Every choice in these rooms begins with what was here first — the stream, the garden, the sand,” said Dayna Lee, principal at PowerStrip Studio, part of the renovation design team. We wanted guests to sense the geography of this place before they ever reach the water.”
To celebrate the milestone, OUTRIGGER Waikīkī Beach Resort is offering the chance to win a package that includes a three-night stay in a Club Ocean View room, round-trip airfare for two, dinner for two at Duke’s Waikiki and a canoe surf session for two with Faith Surf School. To enter the Catch Waikiki’s Next Wave contest, submit a photo, video or story online sharing what you love about the resort by Nov. 16; the winner will be announced Nov. 17.