Sponsor Content: KEEN

The Trailfit Guide to Oahu

Hawaiian native athlete, model, and writer Chelsea Yamase's favorite picks on everything from waterfall hikes and snorkeling spots to poke bowls and shave ice

Chelsea Yamase
Chelsea Yamase

Chelsea Yamase is one of those go-getters who has crafted her own dream job. As a full-time social media influencer, model, and writer, the 28-year-old Hawaii native travels the world for brands in search of magical places, great stories, and stunning sites. Although she has been everywhere from Alaska to Uganda on assignment, she always loves coming home. Born in Kauai, Chelsea landed in Oahu while going to school at the University of Hawaii, where she doubled-majored in journalism and international studies. She says she could literally talk about her love for the islands forever. “It’s this amazing place in the middle of the Pacific where you can be hiking waterfalls in the morning and then going up a volcano with snow in the afternoon.” Here are a few of her favorite sites near Honolulu, on Oahu.

Hikes and Sites

“An awesome beach, beautiful waterfall, and steep ridgeline are the trifecta of the Hawaii experience,” says Chelsea. If starting early, she recommends the Lanikai Pillbox hike (1) for sunrise. About 30 minutes northwest of the city, the 25-minute hike offers “postcard views” of Hawaii. “You see the super-blue water with the finest white-grain sand—all from a ridge overlooking coconut trees. It’s also an easy hike for the whole family.” 

For waterfalls, two of the easiest to reach are Manoa Falls (2), which is by the University of Hawaii at Manoa, and Maunawili Falls (3), which is about 20 minutes away from the city. The latter is a three-mile out-and-back, and good footwear, like Keen’s Terradora boot, is required. “Almost all waterfall hikes in Hawaii will involve some level of mud, slippery rocks, or slippery surfaces, so you need to wear good shoes and be safe.”

For something a bit more adventurous, Chelsea likes the Koko Head Crater (4), near Hawaii Kai on the eastern side of the island and only about 35 minutes from the city. “It’s one of those hikes that you can attack with a friend, but you may be gasping for air on the way up,” she says. It’s only about 1.8 miles round-trip, but the route goes straight up the side of an old volcanic crater. “At the top, there are panoramic views of the ocean and town below.”


Growing up, Chelsea’s dad was a commercial fisherman, so when she says the best poke (fish salad) is at Ahi Assassins (5), right in Honolulu on South Beretania Street, you can bet it’s going to be as fresh as it gets. For a quick post-hike stop, Chelsea likes Andy’s Sandwiches and Smoothies (6), a small spot she discovered while at the University of Hawaii. “It’s full of healthy smoothies and simple sandwiches with few ingredients,” she says. “Leahi Health (7), located on the base of Koko Head about ten minutes away from the main town, also has great smoothies as well as a selection of acai bowls and healthier fare, including homemade kombucha.”

For a memorable dinner, Chelsea suggests a stop in Chinatown, an area that has become popular for foodies in Hawaii. “I love The Pig and the Lady (8), a Vietnamese restaurant specializing in small plates. Afterward you can walk around Chinatown, which is full of great shops and arts and crafts stores.” Chelsea says another great pick is Mud Hen Water (9), a farm-to-table spot with a “limited but amazing dinner menu.” For the quintessential Hawaiian treat, shave ice is a must. “Waiola Shave Ice (10) is the most OG of shave spots,” says Chelsea. “They have all the toppings and tons of bright flavors—it’s what you think of when you think of shave ice. My favorite is coconut with cream topping—a must—and macadamia nut ice cream on bottom.”

On the North Shore—roughly 45 minutes from Honolulu—Chelsea always stops at a few of her favorite food trucks, like Elephant Truck (11) in Haleiwa, which serves Thai food using ingredients sourced from farms within a ten-mile radius. There’s also a slew of food trucks across from Shark’s Cove, a few minutes up the road from the famous Waimea Bay, where you can get everything from ahi sandwiches to acai bowls and healthy salads. Lastly, the Waialua Bakery (12) is the North Shore’s version of Andy’s sandwiches. “They make their own breads, source their vegetables, make their own ice creams, are family owned and operated, and make great food. It’s always busy, but the line moves fast.”


If you want to shop, grab a coffee or a flat white, or just take great pictures, Chelsea has a few favorites. Arvo (13) (Aussie slang for “afternoon”) in the Kakaako neighborhood, an up-and-coming area for art and food, is where Chelsea says to go when you want to Instagram your breakfast. (Since the @ChelseaKauai sensation has more than 330K followers on Instagram, she should know.) The Australian-inspired café is big on “avo” toast and also serves Vegemite, as well as her favorite: matcha pudding with chia, strawberries, and whipped cream.

Across from Arvo, you can head to Paiko (14)—a botanical boutique and coffee bar with a curated selection of plants, flowers, home goods, and onsite workshops—where Chelsea’s also done several photo shoots. Another favorite of Chelsea’s is Malie Organics (15), purveyors of spa and beauty products. It started in Kauai, but there are now a few locations in Hawaii, including Ala Moana and Waikiki. Chelsea also loves Owens & Company (16), which has everything from handmade soaps and sarongs to simple dresses—all locally made. For more unique and vintage wares, she heads to Hound and Quail (17), a funky Chinatown shop and gallery near The Pig and Lady restaurant. “The owners also have fantastic stories,” she says.


If you can only hit three beaches in Hawaii, Chelsea suggests Kailua Beach Park, Hanauma Bay, and Waikiki Beach. The Kailua Beach Park (18), about 25 minutes outside of Honolulu in the town of Kailua, offers “picturesque white sand for about a half-mile, sparking blue water, the finest grain of sand you can see, and beautiful islands off the coast in the distance.” The guys at Kailua Beach Adventures (19) can hook you up with just about anything you need to enjoy it, from kayaks to boogie boards to snorkeling gear. Hanauma Bay (20) is another must-see and must-snorkel. It can be crowded, says Chelsea, but it’s still worth going because it’s a marine protected area and has some of the best snorkeling on the eastern shore. Lastly, Waikiki Beach (21), which also can be very crowded, is also still worth checking out. “It has a great city-by-the-sea vibe, with easy-to-learn-on beginner waves for surfing, gorgeous green-grass parks with palm trees for picnicking or slacklining, and tons of places to rent paddleboards and surfboards, as well as great places for food. If you are going to learn to surf, this is where you go.”

What is TrailFit? 

KEEN's TrailFit is a movement. It's about staying fit and finding your fit. It's about getting out, pushing yourself, and reaching new heights. It's about earning a better view, whether it be of the world or of yourself. TrailFit's best match yet? The new Terradora: a boot designed for those days you can't pick between walking in the city or hitting the trail. Cue the mid-city workout, the post-work hike, or a weekend of playing tourist on your home turf. 

Filed to: