Aloha, my wander-loving, step-collecting tribe! Today we’re swapping cobblestones and city skylines for palm trees and mai tais. Waikiki is calling, and she’s wearing her best shade of turquoise just for us. Lace up (or strap on those walking sandals — arch support matters), put on that gorgeous sunhat, and let’s get moving.
☕ Kai Coffee — Your Hawaiian Jumpstart
Before we even think about selfies, we caffeinate. Kai Coffee has multiple Waikiki locations, so you’re never more than a block or two away from your liquid sunshine. Kai means ocean in Hawaiian, and that’s exactly the vibe you get with every sip. Founded in 2014 by Sam and Natalie Suiter, coffee pros who cut their teeth at Honolulu Coffee Company, Kai serves “aloha in every cup.” Baristas go through weeks of training, beans are roasted on-site, and the macadamia-nut-kissed Kai Latte is basically a warm hug from Waikiki itself. Now, let's go!
🏄 Duke Kahanamoku — The Bronze Surfing King
Head to the Duke Kahanamoku statue on the main drag, Kalākaua Avenue. Born in Honolulu in 1890, this Olympic gold medalist and “Father of Modern Surfing” put Hawaii on the world map for wave riding. Duke’s statue is almost always draped in leis, a sweet local tradition of welcome. Snap your “I was here” pic, throw a shaka, and pretend you surf (I won’t tell). Then head towards the water for a gorgeous beach stroll and perhaps a dip in that warm and wonderful sea.
🌋 Left: Diamond Head / Right: The Pink Palace
When you reach the water, you should see Diamond Head to the left — she’s a 300,000-year-old volcanic crater with views worth the hike (but that’s another day’s 10K). To the right? The OUTRIGGER Waikiki Beach Resort, AKA “The Pink Palace of the Pacific.” Pink, proud, and ready for her close-up, that’s our destination but first — shoes off, toes in that ridiculously blue water. Don’t fight it. Ahh, so worth it!
🍹 Duke’s Waikiki — Mai Tai Me, Please
When you reach the lovely pink Outrigger hotel, come inside and say hello to Duke’s Restaurant. You’ve seen the statue, now let’s enjoy the history and hospitality. Great pictures on the walls tell a surf legend story. This place hums with live music, ocean air, and the clink of mai tais being set on tables. Order one — this is "the" Waikiki mai tai. Fruity, potent, and just dangerous enough to make you consider buying a ukulele you don’t know how to play. Highly recommend – you’ll be floating happily on your journey. Once you have sipped and savored [great nibbles and plate lunch to enjoy], head through the hotel back to Kalākaua Avenue.
🍍 Honolulu Cookie Company — Bite-Sized Aloha
Turn right and follow the scent of butter and sugar to Honolulu Cookie Company. Yes, there are several locations, but don’t let that put you off. Born in Honolulu in 1998, Honolulu Cookie Company set out to bake the ultimate giftable treat — buttery shortbread, baked fresh daily, and cut into their now-iconic pineapple shape (Hawaii’s symbol of hospitality). They dip, drizzle, and infuse it with island flavors like macadamia nut, coconut, and mango. Sample the different flavors before you buy. So yummy. My favorite, the pineapple flavored shortbreads dipped in chocolate — so perfectly crisp and sweet. When you’ve finished this tasty task cross the street.
🛍 International Marketplace — From Banyan Trees to Boutiques
Across the street lies the International Marketplace, a Waikiki landmark since 1956. Once a bohemian maze of tiki huts, food stalls, and live music all tucked under a massive banyan tree where Don Ho crooned and locals shopped for treasures, it got a glossy makeover in 2016 — now it’s a mix of high-end boutiques, cool eateries, and still that legendary banyan tree holding court in the center because Waikiki knows better than to mess with a classic. Head to the back right and you’ll find CocoNene, a delightful store named after Hawaii’s state bird, the nēnē goose.
Here you can create custom picture frames to showcase your trip — the ultimate DIY souvenir. They are so unique and delightful that you may have to make more than one. Once you have finished shopping here, cross back over Kalākaua Avenue and continue with Diamond Head to your back. Turn left into the Royal Hawaiian Center.
🌴 Royal Hawaiian Center — Shady Shopping
Opened in 1979, the Royal Hawaiian Center is built on land once owned by Hawaiian royalty. Now you can enjoy three shaded blocks of air-conditioned shopping packed with luxury brands, local boutiques, and cultural events. So, window shop or go full “charge it.” It’s perfect for escaping the midday sun. You’ll end up near a three-story Tiffany’s and a two-story P.F. Chang’s — it's go big or go home here. Turn left and enjoy this quaint shopping street for some more wandering fun.
🍙 Musubi Café Iyasume — Spam Never Tasted So Good
If you are feeling peckish, a ways down on the left is Musubi Café. Musubi is Hawaii’s no-fuss snack: a slab of rice, a slice of Spam (or egg, or chicken katsu), all wrapped in seaweed. It’s portable, cheap, and somehow tastes better when eaten while people-watching. This is a gorgeous little hole in the wall with great service and yumminess combined. I really like mine with avocado!
👕 KaiAloha Supply — Chickens, Shirts & Charm
Across the street, a favorite shop spot of mine is KaiAloha Supply. It delivers all the Hawaiian shirt energy you need. My personal score? A shirt with a chicken playing a guitar. You don't know about Hawaii’s free-range chickens? They're total survivors. Polynesian voyagers brought their ancestors centuries ago, and when Hurricane Iniki tore through in 1992, coops flew open and the birds never looked back. With no natural predators and plenty of snacks, they’ve taken over beaches, sidewalks, and are ready to strike a pose like they own the islands (because, honestly, they kind of do). When you've shopped enough and are ready for something more substantial, turn right at the end of the street.
🌊 Monkeypod Kitchen — Splash Zone Dining
A little ways down Kalia Road on the left, you'll find Monkeypod Kitchen at the Outrigger Reef. Oceanfront tables + modern Mai Tai + Friday night fireworks? Yes, please. If a rogue wave splashes you mid-sip, just call it “interactive dining.” They have a great happy hour here and excellent service. Plus, you can make a reservation on Open Table to ensure you get the time you want. What a treat and right on the water, so you don’t miss a moment of turquoise waves and ocean breezes.
🌳 The Jungle Path to Hilton Hawaiian Village
Still have steps to burn? Continue down Kalia and meander through the shady park toward Hilton Hawaiian Village, cutting through the Hale Koa Hotel’s tropical grounds. You’ll pass banana trees (with actual bananas — so cool) and enough greenery to make you forget you’re in the middle of Waikiki’s shopping district. It’s a wonderful shady wander that gives great jungle vibes.
🍦 Lappert’s Ice Cream — Ending on a Sugar High
While we are now done with this wander [though there are more shops to check out in the Hilton Hawaiian Village if you are so inclined], you'll want to get back to your hotel with some time to dip in the pool and fully relax knowing you just had the best Waikiki 10K step experience.
🏖 Where I Stayed — The Modern Honolulu
With much love and aloha: Move well. Eat well. Wander well.
Lyn, WanderLynTravel
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