Planning a trip to Hawaiʻi comes with endless possibilities.
That’s where we come in.
Our team is made up of locals who know the island well, from neighborhood coffee spots and surf breaks to hidden food trucks and sunset viewpoints.
Think of this as your inside guide to Oʻahu. These curated itineraries highlight some of our favorite ways to spend a day, from surfing Waikīkī and exploring Honolulu’s art districts to ending the night back at Wayfinder Waikiki for poolside cocktails and a sunset swim.
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ONE DAY ON O'AHU
Curated by Jim, General Manager
Originally from California, Jim spends his ideal island day doing three things: body surfing, eating well, and spending time in the laid-back corners of Oʻahu that made Hawaiʻi feel like home. If you’re short on time but want to experience some of the island’s most iconic stops in a single day, this is Jim’s perfect lineup.
MORNING | Malasadas + The North Shore Drive
Start early with warm malasadas from Leonard’s Bakery. Eat them fresh, preferably still too hot to hold properly, before making the drive from Waikīkī toward the North Shore via H1 and H2.
Around late morning, stop at Ray’s Kiawe Broiled Chicken for their legendary kiawe grilled huli huli chicken. Jim’s order: the half chicken plate with extra sauce. No debate.
MIDDAY | Pipeline Views & Beach Time
From there, head to Banzai Pipeline, one of the world’s most famous surf breaks. Spend some time on the sand watching the waves roll through and, if conditions are calm, cool off with a swim.
This stretch of coastline is classic Oʻahu — surf culture, roadside food stops, and the kind of scenery that never really gets old.
AFTERNOON | Choose Your Route
Sunset Beach + Pie
Keep things slow with a stop at Ted’s Bakery for a slice of their famous chocolate haupia pie before settling in at Sunset Beach for a laid-back afternoon by the water.
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Shrimp Trucks + Scenic Coastlines
Continue on to Giovanni’s Shrimp Truck for a shrimp scampi plate worth the detour, then drive along Oʻahu’s east coast through Lāʻie and Kaʻaʻawa before stopping at Makapuʻu Beach for sweeping coastal views.
EVENING | One Last Sweet Stop
Before heading back to Waikīkī, make one final stop at Ululani’s Hawaiian Shave Ice for one of the island’s best sweet treats.
Back at Wayfinder Waikiki, end the night with a sunset swim, poolside cocktail, or both.
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THREE DAYS ON O'AHU
Curated by Katy, Director of Brand Experience
A global traveler always chasing warm weather, Katy has a way of finding the spots that make a place feel personal. Hawaiʻi has long become her home away from home, and her ideal days on Oʻahu blend scenic hikes, beach afternoons, local food stops, and slow moments that let the island set the pace.
DAY 1 | Ease Into Island Time
Start the morning slow with a smoothie, toast, or banana bread from Alo Café before heading east for one of Oʻahu’s most rewarding hikes. The Lanikai Pillbox trail delivers panoramic views that make the early wake-up worth it.
After the hike, settle into brunch at Over Easy before spending the afternoon at Waimānalo Beach. Soft sand, turquoise water, and fewer crowds make this one of Katy’s favorite beach escapes on the island.
On the way back, cool off with something sweet from Sunrise Shack in Kailua, then take the scenic route through the lush landscapes of Hoʻomaluhia Botanical Gardens.
Wrap up the day with a casual dinner at Paia Fish Market in Waikiki.
DAY 2 | Neighborhood Favorites & Waikīkī Classics
Start your morning with coffee from B-Side before heading out on one of Katy’s favorite loops through Waikīkī. Walk or run along the Ala Wai, past the Honolulu Zoo and Kapiʻolani Park, around Diamond Head, then back along the shoreline to Wayfinder. It’s roughly three miles with plenty of views along the way.
Head to Redfish afterward for breakfast, then spend the afternoon poolside soaking up the slower side of Waikīkī.
For a true local experience, book an afternoon surf lesson with the legendary Moniz Family Surf School before ending the day with sunset dinner and drinks at Hau Tree’s right on the beach.
DAY 3 | Culture, Classics & Sunset Picnics
Grab coffee and incredible pastries to-go from Kona Coffee before heading to Bishop Museum, one of the best places on Oʻahu to connect with Hawaiian history, culture, and storytelling. Wander the grounds and don’t miss the immersive Wayfinding show inside the Planetarium.
For lunch, stop by Helena’s Hawaiian Food for traditional local dishes that have become an island institution. (Be sure to check the hours before you go.)
Afterward, cool down with a treat from Asato Family Shop before heading back to Wayfinder to relax and reset for the evening.
For your final sunset, pick up poke and picnic essentials from Waikiki Market and head to Ala Moana Beach Park. End the night with cocktails at Green Lady.
And one final tip from Katy: if there’s a Wayfinder Waikiki Field Trip happening during your stay, book it. No question.
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FIVE DAYS ON O'AHU
Curated by Scott, Director of Sales & Marketing
Part foodie, part surfer, and always chasing the perfect pau hana, Scott’s version of Oʻahu blends neighborhood favorites, local flavors, vintage finds, and plenty of time in the water. As a longtime kamaʻāina, this itinerary leans into the island spots he keeps going back to.
DAY 1 | Arrival + Wayfinder Rhythm
Check into Wayfinder Waikiki and ease into island time with a quick dip in the pool beneath the palms. No packed schedule yet, just enough time to settle in and let the travel day fade away.
As the sun starts to dip, head down for Sunset Swim at Wayfinder. Use your welcome drink tokens, linger poolside, and ease into your first night in Waikīkī.
Dinner at Redfish keeps things easy with fresh coastal flavors, cold drinks, and the kind of relaxed energy that defines the neighborhood.
DAY 2 | Surf, Side Streets & Pau Hana
Start the morning with breakfast at Redfish before heading out for a surf lesson with the legendary Moniz Family Surf School at Waikīkī Beach. Scott will tell you there’s no better way to understand Hawaiʻi than getting in the water.
After surfing, grab lunch from Pit Stop, one of Hawaiʻi’s favorite local food trucks.
Spend the afternoon cruising Waikīkī by MOKE, stopping at iconic spots like the Duke Kahanamoku Statue, the Banyan Tree, and Diamond Head viewpoints along the way.
Wander through International Market Place and Royal Hawaiian Center for local shops and brands, then stop into Tori Richard for timeless aloha wear and vintage island style inspiration.
Before dinner, head back to Wayfinder for a quick soak in the jacuzzi and a reset before the evening.
For dinner, venture into Kaimukī, one of Scott’s favorite neighborhoods for food. Whether it’s Pig and the Lady, Mud Hen Water, or MIRO, you really can’t go wrong.
End the night tucked away at Vintage Books, a hidden speakeasy perfect for a late-night cocktail and a slower close to the evening.
DAY 3 | Art, Vintage Finds & Downtown Honolulu
Grab coffee and breakfast to-go from B-Side before heading to Bishop Museum. Spend the morning exploring Hawaiian history, culture, and storytelling across the museum grounds and exhibits. Wayfinder guests receive complimentary admission with their room key.
From there, make your way into Chinatown for dim sum at Legend Seafood Restaurant. Go before noon if you can, the wait builds quickly.
Spend the afternoon wandering through Chinatown’s mix of galleries, vintage shops, record stores, and tucked-away local businesses before continuing into the Kakaʻako Arts District.
Scott recommends taking your time here. Explore colorful murals, browse design-forward shops like Hound and Quail and Single Double, and stop through SALT at Our Kakaʻako for snacks, shopping, and people-watching.
For pau hana, grab a beer or glass of wine at Off the Wall before dinner nearby at Merriman’s or Han no Daidokoro for Japanese BBQ.
Head back to Wayfinder Waikiki afterward for cocktails and a final poolside wind-down at Lost + Found.
DAY 4 | Windward Side Wandering
Start the morning with coffee before heading to Mānoa Chocolate Factory for a bean-to-bar tasting experience that offers a deeper look into locally grown Hawaiian cacao.
From there, drive over to Kailua for lunch and a slower afternoon exploring one of Oʻahu’s most laid-back beach towns.
Later in the day, visit Kō Hana Distillers for an agricultural rum tasting rooted in Hawaiian sugarcane traditions and local farming history. It’s one of Scott’s favorite ways to connect visitors to a different side of the islands beyond the beach.
Back at Wayfinder, carve out time for one last long pool session before getting ready for the evening.
End the day with sunset cocktails at the Mai Tai Bar at The Royal Hawaiian. Classic drinks, ocean views, and old Waikīkī energy make it a fitting final night out.
DAY 5 | Slow Mornings & One Last Lap Around Waikīkī
Ease into the final morning with Wayfinder’s Punawai Breathing & Stretching session poolside before heading out for coffee and breakfast nearby. Scott’s picks include Arlo Café, Cream Pot, or Barefoot Beach Café depending on your mood.
Take one last swim, squeeze in a final walk through the neighborhood, and stop by Honolulu Cookie Company for gifts and treats to bring home.
Then it’s checkout time, though Scott would probably tell you this is about the point where most people start looking at extending or booking their next trip.
