Hawaii is a very kid-friendly destination if you know the best places to go, have the right gear and enjoy the great outdoors. The whole reason to visit Hawaii is to experience beauty and a sense of peace. So if kids in tow makes you move a bit slower, let it happen. You may get to sit on the beach longer, enjoying a beautiful Hawaiian sunset while waiting on the kids to finish playing or enjoy a Maui Gold pineapple that you’ve picked up from a Safeway grocery store when you bear off the road for milk.
With ten days of travel time, splitting the trip with four days in Oahu and six in Maui is a great way to experience Hawaii’s top beaches, hiking trails, shopping and aquatic adventures. It also helps that there are direct flights from NYC to Oahu and the travel between Oahu and Maui is only 40 minutes. The flight to Oahu, Hawaii is about 11 hours. On the way home it can be as little as 8.5 and an overnight flight making the first longer flight a distant memory and well worth it after your Hawaiian adventure.
Staying at the Hilton Hawaiian Village as your base for an Oahu visit will make the family trip easy, enjoyable and convenient with its many child-friendly amenities, pools, activities and dining options. A short drive from the airport and a perfect Waikiki beachfront location make it a top choice for a multi-generational family trip. Nicknamed “the Gathering Place,” Oahu is home to the state capital, Honolulu and cultural gems like the US’s only royal palace.
The suites in the Ali’i Tower offer excellent space, amazing beachfront views, large bathrooms with bathtubs for kids, refrigerators to keep your own groceries and great views of the Friday night firework show that people from all over town line up at the beach to watch. From 1930 to present day, the Hilton’s Hawaiian Village has hosted many musical acts and housed many musicians including Michael Jackson and Quincy Jones. Each time Elvis Presley came to Hawaii from 1957 to 1972 he stayed at the Hilton Hawaiian Village. To keep the tradition alive and offer hours of fun and enjoyment for guests of all ages, their Friday night fireworks show which started in 1988, continues today. Grab a Mai Tai or Blue Hawaii and you can spend your evenings at the Waikiki Starlight Luau or watching nightly entertainment at the Tropics and Tapa Bar.
Start your first morning with breakfast at the Tropics Bar on the beach and enjoy a Hula Girl or Açaí Berry Bowl filled with blueberries, bananas and mangoes.
If you decide to venture into Waikiki, Bill’s is another great place to get a fresh Kona coffee, french toast with honey and berries, or eggs and fresh avocado toast. Then grab some beach chairs and towels and lounge around the pool or enjoy the Hilton’s massive lagoon which is the perfect place for paddle boarding.
When you are ready to venture out and explore you can head northeast to Makapu’u for a hike. This is an easy hike along the cliffs on the water with amazing views in all directions and good for children and adults of all ages. Many people with strollers take this trail as it’s paved the whole way and not strenuous. Next stop Kalapawai market in Kailua town for sandwiches and snacks to bring to the beach. Kailua Beach Park has plenty of parking and is one of the nicest beaches on Oahu with soft sand and plenty of space to run, swim and picnic. If you want to venture a little further you can park and follow the paved road into Lanikai and walk down a side street with beach access. This beach feels a bit more local and offers great views of the Twin Islands.
When you head back to Waikiki you can have a family dinner at one of the Hilton Hawaiian Villages’s many restaurants such as Benihana’s or venture out into the city to try Rocky Aoki’s son, Kevin Aoki’s restaurant, Duraku which offers an outstanding sake menu and sushi. Other great options include the new International Marketplace on the top floor of the high end shopping mall where you can get chinese food at Yauactcha, international style food at Herringbone or enjoy top notch martinis and steak at Strip Steak.
Your second morning, now that you know the lay of the land, try some of the Hilton’s ocean activities like kayaking or water bikes. The ice cream and coffee shop across from the Ali’i Tower has excellent iced or hot coffee options and breakfast treats you can bring over to the beach. After you’ve had some beach time head out to the famous north shore of Oahu. Only about an hour drive from Waikiki it’s well worth a visit with the family as it’s one of Oahu’s most notable destinations. Stop for lunch at Cafe Haleiwa where you can try fresh guava, banana bread and pancakes with fruit and honey. Explore the surf shops, art galleries and bikini boutiques before stopping at a food truck for shrimp or shaved ice to bring to the beach. All along the coast are amazing beaches with tons of places to explore and relax. End your day with a MaiTai at Turtle Bay Resort watching the surfers along the coast and don’t miss a chance to take the long way back and see the coast line of Hawaii and it’s magical views all the way home.
Day three you should explore Waikiki and it’s many shops. The Hilton Hawaiian Village has an endless amount of boutiques offering local designs and beachwear as well as bigger shops like Hermès and Louis Vuitton. You can also venture out to the Ala Moana shopping mall offering bigger store options like Nordstrom’s and Macy’s. Then take the kids to dinner at The SurfJack Hotel where you can get pizzas and pastas by the pool where they play movies and have live music.
Last Oahu morning at the beach you can get involved in a game of family beach volleyball or just take a stroll along the water jumping in and out of the waves. Heading to Maui is easy as the airport is small, the flight is short and you only need to arrive an hour before your flight.
With many great memories of Oahu, next stop Maui and the Grand Wailea Hotel at Wailea beach. The closest airport is Kahului (OGG) and the suggested one when staying in Wailea about 35 minutes away. A lush mix of hills and valleys, Maui offers jaw-dropping views at nearly every turn. See migrating whales, play golf on scenic courses and tour the legendary Road to Hana.
This Grand Wailea is a playground for people of all ages and if you never wanted to leave there would be enough to do on the property for everyone all week. Each tower has their own valet so you can park close to your room as the hotel is very big making it a long walk with kids from the main lobby to other towers. You are a five minute walk from the Shops at Wailea so if you need any souvenirs or want to do some shopping you don’t even have to drive. The hotel also has many cafes, restaurants, boutiques and art galleries offering hours of enjoyment when you want a break from the beach. A must try for dinner after a day of traveling is the famous Humu Humu with choices like mahi mahi, pink snapper and tiger prawns. They offer mocktails for the kids and a great tropical cocktail menu for the adults. The restaurant gives kids an adorable stuffed animal after the meal keeping them entertained as everyone finds their way back to their rooms after a long day.
The Grand Wailea is a gigantic property filled with numerous pools, water slides, a Grotto swim up bar, a lazy river, an adults only pool, a jacuzzi inside a cave, and even a Tarzan swing. You can spend the whole day just floating through the pools, climbing up and down the maze of slides and playing volleyball in the pool. After a few days of exploring Oahu a full day at the pools just relaxing and swimming in Maui is exactly what everyone will enjoy. You can have dinner at the hotel at Bistro Molikini overlooking the beach at sunset.
Day six and it’s time to explore Maui. First fill your belly at the breakfast buffet offering everything from sweetbread french toast to a mango granola parfait or build your own omelette and try a fresh cup of pineapple or orange juice. Head out on a whale watching adventure if you are lucky enough to be there in season from December to April. Kai Kanani offers boat trips just ten minutes away out of the harbor. The boat is a 65 foot catamaran that only holds up to fifty people. They offer snacks, sweets, drinks and a great friendly staff. Just make sure you wear clothes that can get wet or bring a towel as you have to climb in the water to board. Seeing the whales is an adventure and definitely a bucket list experience the kids will love. The boat also offers an indoor galley so that you can take a break from the sun or sit inside and enjoy a drink. It’s worth a stop after at Makena Beach, less than five minutes up the road, to jump in the ocean and see one of Maui’s most beautiful stretches of beach.
When back at the hotel head over to the Hawaiian luau on the lawn and the amazing hula dancers and music will entertain you for hours under the stars. First take some pictures with their professional photographer on the beach at sunset and you may even see some whale tales out in the water right off the beach as they swim about. These are a great souvenir to take home.
Day seven you can grab a snorkel and swim right out off the beach. Underwater Maui is amazing and offers endless types of tropical fish, coral and sea turtles. Right off the beach is where many of the snorkel boats stop after Molokini and since you are lucky enough to be staying right on Wailea beach, just jump in the water with your mask and flippers and explore. You can rent equipment right at the hotel. Most days the water is calm and clear allowing for great visibility and relaxed snorkeling for kids. At night you can venture into Kihei town to try the family-friendly restaurants like Paia fish market or Thai Bistro.
Day eight try a light breakfast at Cafe Kula offering coffee, yogurts, pastries and egg sandwiches. Let the kids go visit The Rock which has tons of games and toys for kids to play with, movies to watch and more while you enjoy some well deserved me time at the spa. A Hawaiian favorite is the Lomi Lomi massage. Before your treatment you can enjoy the various hot tubs, steam room, sauna, salt pools, waterfall shower and Japanese shower. As you head up to your treatment they will give you a honey mango body scrub and cleanse your whole body with water. The relaxation room overlooks the pool and fountains so allow time to sit and soak it all in. If you have time to hit the gym before it has a basketball court, racquetball court, three rooms of machines, yoga classes and a weight room. For the afternoon take a trip to Paia town on the north coast. This town has lots of surf shops and boutiques and in the winter some of the best surfing on the island at the beach. Make a reservation way in advance and have dinner at Mama’s Fish House. A Hawaiian favorite and well worth the 40 minute drive from Wailea.
On the last day before you leave spend it at the hotel and lounge around in all of the pools, exploring the waterslides and outdoor cafe for lunch. The kids can enjoy chicken fingers, burgers and light bites while you enjoy a burger and Mudslide topped off with an Oreo cookie. The property also has beautiful ponds filled with koi fish and flowers making a walk around the property a relaxing way to enjoy time too. Along the beach is a beautiful path that you can follow down for a few miles exploring the coast line. Little coves and different paths offering beach access make it an interesting way to wander and spend the afternoon as you reflect on your stay in Hawaii knowing that soon you’ll be back to reality. Head to Gannon’s about five minutes up the road on the Wailea Golf Course for dinner where you can sit outside and enjoy the evening under the stars.
As you head back to the airport to catch your flight stop for some souvenirs in Kihei at the market in town or at ABC stores for some 100% Kona coffee to bring back for friends. The flight to Oahu is short and allows you time to break for lunch before boarding your plane back to the mainland.
With fond Hawaiian memories, Mahalo until next time…
- Hawaii Tourism: http://luxegetaways.info/hawaii-tourism
- Hawaiian Airlines: http://luxegetaways.info/hawaiian-airlines
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