A row of colorful surfboards are standing upright in front of palm trees, with a hotel building visible in the background.

Wayfinder's Guide to O'ahu

A tropical beach with golden sand, turquoise water, rocky outcrops, and green hills in the background, under a partly cloudy sky.

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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  • A weathered sign for “LANI North Shore Shop” with a shark mascot and a rooster, advertising food, gas, and shops along a highway.

    One Day O'ahu Itinerary

    Morning: Malasadas + The Drive North

    Start your day with warm malasadas from Leonard's Bakery. Eat them fresh, then drive from Waikīkī to Haleʻiwa via H1 and H2.

    Around 10:30 AM, stop at Ray's Kiawe Broiled Chicken for their famous kiawe grilled huli huli chicken. Order the half chicken plate and grab extra sauce.

    Midday: Pipeline Beach

    Head to Banzai Pipeline, one of the world’s most famous surf spots. Enjoy lunch on the beach and watch the waves. If conditions are calm, take a swim.

    Afternoon Options:

    Sunset Beach + Pie
    Stop at Ted's Bakery for a slice of chocolate haupia pie, then relax at Sunset Beach.
    - or -
    Kahuku Shrimp + Coastal Drive
    Continue to Giovanni's Shrimp Truck for their famous shrimp scampi plate. Then drive Oʻahu’s east coast through Laʻie and Kaʻaʻawa before stopping at Makapuʻu Beach.

    Evening: Sweet Finish in Honolulu

    Before returning to Wayfinder Waikiki, stop at Ululani's Hawaiian Shave Ice for one of the island’s best shave ice treats.
    End the day back at Wayfinder with a sunset swim or poolside cocktail.

  • A lush, rugged mountainside with a sharp peak, green cliffs, and a valley below dotted with fields and distant hills, under a cloudy sky.

    Five Day O'ahu Itinerary

    Day 1: Arrival + Wayfinder Vibes

    Check in at Wayfinder Waikiki and settle into island time.

    Head straight to the pool for a quick travel recovery swim and relax under the palms.

    Evening: Sunset Swim + Dinner
    Use your welcome drink tokens during Wayfinder’s Sunset Swim.

    Grab dinner and cocktails at Redfish for coastal flavors and a relaxed first night in Waikīkī.

    Day 2: Waikīkī Surf + Beach Day

    Morning: Breakfast + Farmers Market
    Start the morning with breakfast at Redfish.

    Then head to the KCC Farmers Market for fresh fruit, local snacks, and island favorites.

    Lunch: Market Bites
    Grab lunch from one of the market vendors before heading back toward Waikīkī.

    Afternoon: Surf + Explore Waikīkī
    Take a surf lesson with Moniz Family Surf at Waikīkī Beach.

    Rent a MOKE and explore the neighborhood.

    Stop by International Market Place and Royal Hawaiian Center for shopping, restaurants, and local brands.

    Visit Tori Richard for classic aloha attire before your night out.

    Evening: Dinner in Kaimuki
    Return to Wayfinder for a quick jacuzzi session.

    Head to Kaimuki for dinner at Pig and The Lady, MIRO, or Mud Hen Water.

    Finish the evening with cocktails at Vintage Books speakeasy.

    Day 3: Downtown Arts + Kakaʻako

    Morning: Coffee + Culture
    Grab coffee and breakfast to go from B-Side Coffee Bar.

    Visit Bishop Museum to explore Hawaiian history and culture. Wayfinder guests receive complimentary access with their room key.

    Lunch: Chinatown Exploration
    Head to Chinatown for dim sum at Legend Seafood Restaurant. Arrive before noon to avoid the wait.

    Spend time wandering the neighborhood’s art galleries, vintage clothing stores, and eclectic local shops.

    Afternoon: Kakaʻako Arts District
    Continue to Kakaʻako to see the neighborhood’s colorful murals and street art.

    Browse local boutiques and design shops like Hound and Quail and Single Double.

    Stop by SALT at Our Kakaʻako for shopping, snacks, and local bites.

    Late Afternoon: Drinks + Dinner
    Grab a beer or wine at Off the Wall.

    Walk to Merriman’s for dinner or try Japanese BBQ at Han no Daidokoro.

    Evening: Back to Wayfinder
    Return to Wayfinder Waikiki for cocktails and poolside time at Lost + Found.

    Day 4: Craft Tours + Windward Coast

    Morning: Coffee + Chocolate Tour
    Start the day with coffee at B-Side Coffee Bar.

    Take a tour of Manoa Chocolate Factory for bean-to-bar tastings and a look into Hawaiian cacao production.

    Lunch: Kailua Town
    Drive to Kailua for lunch and explore the town’s relaxed beachside vibe.

    Afternoon: Rum + Hawaiian Agriculture
    Visit Kō Hana Distillers for an agricultural rum tour and tasting that highlights Hawaiian sugarcane traditions.

    Late Afternoon: Pool Time
    Return to Wayfinder Waikiki and enjoy one final long pool session.

    Evening: Sunset Drinks
    Head to the Mai Tai Bar at The Royal Hawaiian for sunset cocktails and classic island bar food.

    Day 5: Wellness + Last Strolls

    Morning: Coffee + Stretch
    Start the day with one last coffee from B-Side Coffee Bar.

    Join the Punawai Breathing & Stretching session poolside at Wayfinder Waikiki.

    Late Morning: Final Pool Dip
    Take one last quick swim before packing up.

    Stop by Honolulu Cookie Company for gifts and treats to bring home.

    Departure
    Check out at the front desk and start planning your next stay at Wayfinder Waikiki.