Planning for your Waikiki vacation
A family friendly 5-day itinerary for Honolulu and Waikiki
Waikiki is where island adventure meets easygoing beach days and rich Hawaiian culture. Families come for calm turquoise water, iconic landmarks and warm hospitality, and leave with the kind of memories that replay for years. This five-day itinerary brings the best of Waikiki together in a way that feels simple, relaxed and full of discovery, all while staying close to the comfort of your OUTRIGGER resort.
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Breakfast with a view at Voyager 47 Club Lounge
There is no better way to arrive in Waikiki than by stepping onto an oceanfront terrace with a plate full of tropical fruit and pastries. If you’re staying in a club room or suite at OUTRIGGER Waikiki Beach Resort or OUTRIGGER Reef Waikiki Beach Resort, start your day at the Voyager 47 Club Lounge. The lounge sits above the beach, so you can sip fresh Kona coffee and enjoy a variety of breakfast offerings while watching early morning surfers glide across gentle waves. It’s peaceful, scenic and instantly sets the tone for your vacation.
Settle into Waikiki Beach
Waikiki Beach is world famous for a reason. The sand is soft and warm, the water is clear and calm and the shoreline stretches for miles. Families can spread out under umbrellas, build sandcastles or float in the shallow water where small waves roll in like a friendly greeting. It’s the easiest way to shift into island time.
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Learn to surf with Faith Surf School or Gone Surfing
Waikiki is one of the safest places on Earth to learn to surf thanks to long, rolling waves that break gently and predictably. Faith Surf School and Gone Surfing teach right on the beach, so you’ll start with a quick lesson on the sand before paddling out to try your first ride. For many families, this becomes the highlight of the entire trip as everyone cheers each other on.
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Treat the family to Hula Pie at Duke’s Waikiki
After a big morning on the beach, head to Duke’s Waikiki. The restaurant sits right along the sand with open air seating and that unmistakable Waikiki energy. Order the famous Hula Pie, a towering slice of macadamia nut ice cream dessert that has been a tradition for generations of visitors. Adults can sip something cold while kids retell the story of their first wave.
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Live music nightly at The Home of Hawaiian Music
When the sun begins to set, follow the sound of slack key guitars to Kani Ka Pila Grille at OUTRIGGER Reef Waikiki Beach Resort. Every night, award-winning Hawaiian artists perform here in an intimate setting where families can relax together over dinner. The warm glow of string lights and the smooth rhythm of island music set the perfect tone for your first night.
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ダイヤモンドヘッドクレーターのハイキング
Wake early for a family-friendly hike up Diamond Head, one of Oahu’s most iconic landmarks. The trail is well maintained and takes you up an ancient crater rim. Along the way, enjoy the view of Waikiki from above as the morning light softens over the ocean. At the summit, the view stretches for miles in every direction.
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Snorkel at Hanauma Bay
After the hike, head to Hanauma Bay, a protected marine sanctuary where the water is calm and filled with fish of every color. Kids can wade into shallow areas and watch schools of reef fish dart through coral, while adults snorkel farther out to explore deeper sections. It’s one of the easiest places for families to safely see Hawaii’s underwater world.
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Sail along Waikiki on a catamaran
A catamaran sail off Waikiki is windy, refreshing and often full of surprises. You may spot dolphins, turtles or flying fish as the boat glides over turquoise water. The skyline views are stunning, and the whole experience feels carefree and joyful.
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Duke’s on Sunday with Henry Kapono
If your trip falls on a Sunday, you’re in luck. Duke’s Waikiki hosts legendary musician Henry Kapono for a sunset performance that brings visitors and locals together. Families gather near the beach, toes in the sand, as the music floats over the shoreline. It’s a moment that feels timeless.
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Outrigger canoe surfing or sunrise yoga
For a burst of adventure, try outrigger canoe surfing, a thrilling ride on the same style of canoe ancient Hawaiians used. You paddle as a team and catch waves together.
Or, if you’d rather ease into the day, join sunrise yoga at OUTRIGGER Waikiki Beachcomber Hotel for a calm, refreshing start.
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Pearl Harbor or beach relaxation
History lovers can visit Pearl Harbor for exhibits and memorials that bring the events of 1941 into clear perspective. If your family prefers something slower, lounge by the resort pool, book a cabana or enjoy a relaxed lunch at Sunrise Shack with tropical bowls and bold bullet coffee.
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Discover a new experience with the concierge
Stop by the concierge desk at your OUTRIGGER resort. Hosts can help plan unique experiences like guided snorkel tours, waterfall hikes or local food adventures. Or head back to your room for downtime and tune in to OUTRIGGER Journey TV for stories about Hawaiian culture, art and ocean life.
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Celebrate your trip with a family dinner
Choose from crowd favorites like Appetito Craft Pizza & Wine Bar for Neapolitan style pies, Tanaka of Tokyo for an entertaining teppanyaki experience or Hawaiian Aroma Caffé for coffee and dessert in Waikiki’s most photographed café.
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Complimentary cultural activities at OUTRIGGER
Start your second day by learning about the land you’re visiting. Each OUTRIGGER resort and hotel in Waikiki offers its own selection of complimentary cultural activities led by local hosts who share traditions passed down through generations. Depending on where you stay, you may learn to weave a bracelet, string fresh flowers into a lei or play simple chords on a ukulele. Kids love the hands-on fun, and adults appreciate the deeper connection to Hawaii. Be sure to check with the front desk for the current schedule of activities at your property.
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Visit Iolani Palace
Leave the beach behind for a moment and step into Hawaii’s royal history. Iolani Palace is the only royal palace in the United States and once served as the home of the Hawaiian monarchs. Touring its halls gives families a chance to understand Hawaii’s heritage in a vivid, memorable way. The building itself is stunning with grand staircases, ornate woodwork and beautifully preserved rooms and artifacts.
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Explore the Waikiki Aquarium
Just steps from the shoreline sits the Waikiki Aquarium, a family-friendly spot filled with colorful coral displays, tropical fish and Hawaiian monk seals. It’s the perfect low effort, high reward activity after a big morning out. Kids can get up close to reef creatures they may later see while snorkeling.
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Dinner with a view at Monkeypod Kitchen
As the sun sets behind Diamond Head, take a seat at Monkeypod Kitchen, Waikiki’s hottest new restaurant. The restaurant is known for farm fresh dishes and a signature mai tai crowned with a lilikoi foam that tastes just as bright as it looks. The open-air setting lets you watch the last light fade over the water as the family unwinds from the day.
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Coral Kids Club and resort time
Located at the OUTRIGGER Reef Waikiki Beach Resort but open to the public, sign your keiki up for the Coral Kids Club. Trained hosts lead educational activities about the ocean, marine life and Hawaiian culture. While the kids play, parents can enjoy a cup of coffee downstairs at Monkeypod Kitchen or a peaceful walk along the beach.
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Explore Waikiki Beach Walk
Wander through Waikiki Beach Walk, a lively area filled with local boutiques, bakeries and restaurants. It’s a fun place to browse for souvenirs or pick up a treat to fuel you through the rest of the day.
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Art walk at OUTRIGGER properties
All of OUTRIGGER’s resorts and hotels in Waikiki feature curated art collections celebrating Hawaii’s creative community. Stroll through the property corridors and discover everything from modern island landscapes to traditional motifs reimagined by local artists. Be sure to stroll through the OUTRIGGER Waikiki Beachcomber Hotel, Hawaii’s first craft hotel, and see and experience the artwork from some of Hawaii’s premier artists.
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Dinner, music and a show
Choose your evening vibe:
- Hula Grill Waikiki for open air dining with ocean views (they also have the Hula Pie!)
- Blue Note Hawaii for a family friendly show featuring jazz, comedy or island talent
- Maui Brewing Co. for locally crafted beers, hearty dishes and live music at the largest bar in Waikiki
Each option offers a relaxed, lively setting perfect for families.
If you want a wow moment, end one of your nights at 'Auana, Cirque du Soleil’s resident show in Waikiki. This must-see performance blends Hawaiian music, breathtaking choreography and gravity defying acrobatics into a story that feels both deeply local and visually spectacular. Dancers move like ocean currents, chants and original Hawaiian language songs fill the theater, and world class performers take to the air in ways that leave the entire audience speechless. It is an unforgettable evening that captures the spirit of Hawaii in a way no other show can, and it is the perfect way to end a night in Waikiki.
