Oahu Beyond Waikiki: 2-Week Family Adventure from Ko Olina

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Advisor - Kristen Heckel
Curated By

Kristen Heckel

  • Nature Escapes

  • Active Travel

  • Luxury Travel

  • Family Travel

  • Oahu

  • Island

Advisor - Oahu Beyond Waikiki: 2-Week Family Adventure from Ko Olina
Curator’s statement

A two-week family escape to Oahu, Hawai'i — anchored at Disney’s Aulani Resort in tranquil Ko Olina — is more than just a vacation. It’s a journey of reconnection. Surrounded by the island’s lush landscapes, vibrant wildlife and the gentle rhythm of the Pacific, first-time visitors are often struck by the life-changing beauty and spirit of aloha that defines Hawai'i. Days are perfectly balanced between the peaceful, sun-soaked shores of Ko Olina and thrilling island adventures — from waterfall hikes to snorkeling with sea turtles. This itinerary invites families to disconnect from the noise of everyday life and rediscover themselves through nature, wonder and shared experiences.

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Day 1: Honolulu arrival

Arrive in Honolulu and pick up your rental car to ensure freedom to explore throughout your time on Oahu. Anywhere you go on the island is within approximately an hour drive.

Drive straight to your hotel to grab some dinner and relax after what was inevitably a long flight. Get comfy, check out your amazing room with decor honoring Polynesian history and go say hello to the Pacific ocean!

Head to Ama Ama for a locally-inspired, open-air dinner with a beautiful view of your first Hawaiian sunset over the Ko Olina lagoon.

Day 2: Snorkel and shopping

Spend a day getting to know the resort and town that will be your home for the next two weeks. Go visit the kids club to get your children signed up for some activities and explore the pools and lagoon right out front of the hotel. Try out some snorkeling right at your doorstep on the Aulani man-made lagoon if you’re nervous to try it for the first time. Or head straight to the ocean to check out the beautiful fish right at your doorstep.

Walk across the street to the little shopping center to check out the food and shopping options available right in your neighborhood. Stop into the Island Country Mart for any essentials you need throughout your stay and some quick and budget-friendly eats.

Day 3: Drinks and local fare

Drive into Honolulu to explore Ala Moana Shopping Mall and grab dinner at a local gem of a restaurant, Merriman’s. Experience award-winning, farm-to-table, local cuisine. Be sure to try the Meeriman’s Mai-Tai for the most delicious local drink on the island.

Day 4: Island exploration

Spend your next day touring the island with a local to quickly, but thoroughly hit some of the biggest highlights and get a feel for anything you might want to revisit or explore more deeply later in your visit. With any luck, your guide will take you to a local shrimp farm for lunch to indulge in the best buttery, garlic shrimp of your life. Nothing quite like eating fresh shrimp, smothered in garlicky butter in the fresh air with a local singer serenading you with classic island music.

You’ll see everything from beautiful lookouts, to the Buddhist Byodo-In Temple. Sample local food and spot native wildlife (cross your fingers for sea turtles!) Enjoy a stop in Waimea Valley for a refreshing dip in the waterfall. Stop at the historic Dole Plantation, all while your local guide talks story about the island’s history.

Day 5: Activities and pool

Spend another day enjoying the fabulous Aulani resort and Ko Olina area. Check out the daily activity schedule or just relax by the pool with a pina colada in hand. Be sure to grab some Shave Ice or the iconic Pineapple Whip from the stand on the resort, the only treats on the island you’ll find with Mickey ears ;)

End your resort day with a Luau to experience the traditional Hawaiian dance, culture and food.

Day 6: Kailua Beach

Take a drive to Kailua Beach for the day. Park in the main beach parking lot and walk over to the Lanikai Pillbox Trail entrance. Hiking up to the first pillbox is totally accessible for even young children (my youngest was five at the time) and will reward you with some incredible, panoramic views.

After walking back from your hike, grab a quick lunch at The Sunrise Shack or Kalapawai Market before picking up your kayaks at Kailua Beach Adventures.

Ocean kayaking is not for the faint at heart, but is totally doable with your kiddos in tow in a double kayak. Head out to Popoai Island and hop out to walk around and explore the island sanctuary full of crabs and birds.

Reward yourselves with some swim time back at the beach before returning back to Ko Olina for some dinner.

Day 7: Explore the North Shore

Drive up to the North Shore to check out Haleiwa shopping. Grab shaved ice at the famous Matsumoto Shave Ice, and some more amazing garlic shrimp at Giovanni’s Shrimp Truck. While the North Shore is home to big waves in the winter, Waimea Bay turns into the perfect swimming and snorkeling spot in the summer. Spend some time in the sand and waves before heading back to Ko Olina.

Be sure to check out the Patagonia store in Haleiwa for exclusive styles you’ll only find in Hawaii!

Day 8: Sailing and canoe

Start a day back at the resort with a Sailing Canoe adventure. Schedule a private tour and your guide will anchor and give you time to snorkel! This is an excellent opportunity to see wildlife (I’m talking sea turtles and urchins along with the expected tropical fish) and hear from a local about keeping Hawaiian culture alive through building the classic sailing canoes and sharing their history and meaning with visitors.

Head back for another day full of whatever version of relaxation or adventure you want at your fabulous resort. End the day with a family-friendly and festive dinner at Aulani’s Makahiki

Day 9: Tours and parasail

Today, you’re going to start your day driving into Waikiki to explore the underwater world of the Pacific Ocean with Atlantis Submarine Tour. This amazing organization uses funds from their tours to care for the reef. It ensures a healthy environment for marine life to thrive, giving you a fabulous experience and taking care of the precious ocean.

Next stop is a Hawaiian Parasail experience. Ages five and up are welcome to get strapped in and ascend into the skies for a unique view of the Oahu coastline.

You have one more adventure in Honolulu to round out the day, a banana boat ride at Koko Marina! Grab some food and a cold beer at the Kona Brewing Hawaii Kai. This restaurant is right next to your banana boat office to round out your adventurous day in Honolulu.

Day 10: On the water

Today, you’re staying in Ko Olina, but still getting some time off the resort. Start your day with a Catamaran sail from Ko Olina Marina, including a light lunch and snorkel stop. If you’re lucky, you’ll see dolphins dancing in the boats wake, sea turtles floating up for a quick breath of air, and a variety of tropical fish.

Return back to the resort for a relaxing afternoon. End your day with a dinner at Monkeypod by Merrimans across the street, a sister restaurant to the Merrimans’ in Honolulu. Along with another amazing Mai Tai, be sure to order one of their incredible cream pies for dessert. The Chocolate and Coconut were our favorites!

Day 11: Spa and relax

Time to settle into your resort for the day. Make sure the kids are signed up for some time at the kids club and hit the Aulani spa, Laniwai. Purchase of any full-service spa treatment will get you access to Kula Wai. This is the outdoor hydrotherapy garden with a variety of soaking pools and showers to continue your relaxation after your treatment. Be sure to schedule enough time in the kid’s club for you to enjoy this part of your spa visit!.

End the day walking next door to visit the Four Season’s upscale, outdoor Mina’s Fish House. Time your dinner just right to have a beautiful sunset view over the lagoon while you dine.

Day 12: Paradise Cove

Today, you’re staying in Ko Olina again, but venturing out to a different lagoon. The Ko Olina lagoons are lovely and calm for swimming all day. Just up the coast, you’ll find Paradise Cove. This is a natural lagoon that is home to sea turtles, sea cucumbers and all kinds of fish you won’t see in your resort-front lagoon. For the extra adventurous, walk down the beach, take a right and keep on walking. You’ll end up climbing over some rocks and picking your way through rugged areas to reach Paradise Cove Beach. If you’re not up for that, just head out of the resort and take the sidewalk to the Paradise Cove parking lot to access the lagoon. Don’t forget your snorkeling gear!

Day 13: Kualoa Ranch

Take one more day trip up to Kualoa Ranch for a tour, including lunch, that will take you to a secluded beach for the day. Tour includes sand activities and sports equipment, water equipment for use, a canoe ride out to the sandbar, and a glass bottom boat ride. This gives you a chance to see another side of the island.

Make it back to your resort for the classic sunset view over the Ko Olina lagoon. Grab takeout and sit in the grassy lagoon area to watch the brilliant colors transform as the sun makes its descent beneath the horizon.

Day 14: Farewell

Spend your final full day in the beauty and peace of Ko Olina and your resort. Grab food from your favorite Ko Olina spots, don’t forget one final Shave Ice, and maybe an extra cream pie or Mai Tai from Merriman’s!

Be sure to catch your final sunset over the Ko Olina lagoons.

Need to know

Be sure to rent a car so you can freely explore all the island has to offer!

Advisor - Kristen Heckel

Travel Advisor

Kristen Heckel

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