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A Billionaire Vacation in Hawaii Through the Eyes of a Seven Year Old Boy

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I was excited to experience another luxury, billionaire style adventure with my seven year old nephew Jake. Our last journey was a snowy glamping excursion in Montana, but this time we needed sun, surf and the best that Hawaii had to offer. Specifically the islands of Maui and Oahu, two very popular destinations for families.

Our journey began when our town car dropped us off at the American Airlines First Class departures in Los Angeles. We were whisked through security via the airlines exclusive Flagship Five Star service with a curbside greeter taking us around the public and long lines and directly to the lounge for breakfast.

After a very easy flight, we arrived in Maui, the second largest of the Hawaiian Islands. The tropical sun was shining down on us and the lack of trade-winds made the temperature soar as we departed the plane. We were greeted outside the door of the airplane and quickly taken to our waiting car with private driver and guide. We were lucky to be hosted by the best hotel on the island, the amazing Andaz Maui at Wailea Resort & Spa. Sparkling, fresh and luxurious, this resort gives the venerable Four Seasons Hotel a run for their money.

Located on Maui’s southwestern coastline along Mokapu Beach, the 15-acre beachfront resort features 300 guestrooms and suites, ten luxurious two-four bedroom residential villas, cascading infinity pools, an enormous 14,000 sf spa and two of the best restaurants on the island, including the famed Morimoto Maui.

Once we pulled up to the gorgeous outdoor entry of the resort we were met by a large group of staff, all bearing lei for Jake. His neck was loaded down with so many fragrant flowers and Kukui Nuts that his smile was from ear to ear. One of the concierges gifted Jake with a hand-carved wooden turtle necklace and offered up another lizard necklace for him to retrieve once he spots his first lizard on the property. With yummy fresh lavender lemonade in hand, our luxury week began.

We were taken to our decadent three bedroom, beachfront villa overlooking the spectacular Pacific ocean. The enormous 4,482 sf villa with four bathrooms and private plunge jacuzzi also featured a modern Miele designed kitchen, lava stone floors, sliding glass walls and advanced one button window screen closures as well as a huge outdoor lanai with Viking range barbecue grill.

Jake proceeded to jump up and down on his massive beachfront bed (sorry Andaz) with excitement of the activities to come, and for the massive amount of goodies that were displayed on the expansive dining room table. I am a big supporter of local, homegrown products and companies everywhere I travel, so I wanted to make sure to highlight the best products Maui had to offer including Holly Engelmann’s amazing Ala Lani Bath & Body, Maui Fruit Jewels Artisan candy, delicious Hot sauces from Adoboloco, Maui Grown Coffee and the very best sparkling wine from MauiWine at Ulupalakua Ranch.

We spent the afternoon at leisure by the swimming pool before having an early dinner prepared in our villa by the resorts Executive Chef Isaac Bancaco. While dinner was being prepared, Jake was surprised with a private ukulele lesson by the islands famous virtuoso Derick Sebastian. Derek took Jake to the sandy beach where he taught him the basics in ukulele and they performed “Somewhere Over the Rainbow” to the delight of guests walking nearby. What a special man Derick is, and his patience and enthusiasm for young children is infectious. Everyone needs to have this experience.

Following our musical sojourn, Jake was treated to a private hula dancing lesson by the beautiful Tehani Aina Melchor. After a lot of practice they were able to perform a traditional dance on the lawns fronting the villa. She presented him with a Maile King headband made of leaves as we joined the dinner party at the villa.

A multi-course dinner was prepared on our lanai with the waiter and chef, featuring all fresh local ingredients. Jake was enlisted to help Chef in the kitchen and quickly became an expert at creating a modern Luau feast. Jake hopped up and down behind the counter as Chef instructed him in the fine art of presentation and garnishing the delicious local food.

We watched the magnificent sunset while sitting on the large outdoor dining table on the villa’s lanai, and as the sky darkened we heard drums begin to play behind the bushes. Suddenly a fire dancer appeared and began to perform the most amazing private show just for Jake. Afterwards he presented Jake with his own custom made fire pole to take home with him. This became his favorite souvenir from the trip.

The next morning Chef Ben Marquez enlisted Jake to prepare us a lavish breakfast in our villa before our SUV transported us to a thrilling private experience at the Maui Zipline Adventure. Jake had three guides dedicated to him privately as he soared on 900 foot lines over swaying palms and overlooking the spectacular Haleakala volcano. This experience is great for young adventurers unlike many zip line companies that are primarily for adults. The guides are so kind and will even fly tandem with kids if they are scared. They were so much fun and made the adventure a true delight. Andaz also provides special gourmet box lunches for their guests to take on this excursion

Our afternoon was spent in blissful leisure as Jake enjoyed his own decadent spa treatment in the villa. His massage table and therapist were waiting when we arrived. While his mother was having an adjacent longer traditional lomilomi massage, Jake was quietly escorted out to the villa’s lanai to create a custom milk bath and scrub for his mom. The resorts delightful Apothecary consultant Teresa taught Jake about the unique healing properties and benefits of each oil and serum as well as letting him pick out his favorite fragrances and essential oils to create the custom blend.

The best was yet to come when Jake’s custom Mixologist Travis showed up later to teach him how to make delicious fruit juice concoctions and mocktails. To enliven the experience he provided mustache straws and Travis surprised Jake with several gifts, an autographed professional baseball and a super cool parachute toy that they used on the lawns after the mixing class. Travis is the most amazing guy with kids of all ages and you must seek him out when you visit Maui. His crazy handlebar mustache alone will have you grinning ear to ear.

That night Jake had his own table reserved in the kitchen surrounded by the culinary team and Chef de Cuisine Ritchard Cariaga at the Ka’Ana private Chefs table. The interactive experience is so fun while watching them prepare your meals in the open concept kitchen. Jake quickly became a natural at adding the final touches to our meals.

We were up early the next day for a custom and very private outrigger and snorkel adventure with the Andaz Beach Crew. Andaz also launched a new partnership with GoPro, allowing guests complimentary access to GoPro Hero 4 cameras during their stay with full access to the GoPro Lab and official editing software. GoPro provided Jake with a special package prior to his trip including the Hero 4 and the Hero Session and tons of equipment to use along. I'm excited about GoPro's new Karma Drone coming out in 2016 that will revolutionize the experience.

The Andaz Beach Crew enlisted our guide for the day, the amazing local Kekoa Cramer. Handsome, charming and so lovely with young visitors. Kekoa took us out on a private Outrigger journey departing from the resorts Mokapu beach. We paddled along the coast until we arrived at Kekoa’s favorite snorkeling spot. The Beach Crew provided everything from fins to goggles and we jumped in.

Kekoa knows what excites young visitors and he dove to the bottom of the coral reef and pulled up amazing sea creatures for Jake to hold and learn about. First was a Slate-Pencil Sea urchin in vibrant red and then a playful octopus which held on leaving tentacle suction marks on Jake's hand... much to his delight. It was however the large Green sea turtles that truly made the day special. Swimming all around Jake inquisitively while popping their massive heads up and staring at you, they are a beautiful addition to the Hawaiian waters and well protected.

Kekoa spent the day with us and took us on another adventure on the road to Hana, this time to the magnificent bamboo forest, Na'ili'ili Haele Stream & Waterfalls. Hiking with Kekoa was a breeze and he made sure we were safe the entire time. He even let Jake ride on his back as they swam up to and under the large beautiful waterfall after jumping into the chilly pools. We stopped at a locals only beach, (Kekoa is well known in these parts) and we ate a picnic lunch provided by the resort while watching the surfers and hanging out with the giant sea turtles on the beach.

It was our last evening in this amazing resort and we wanted to spend it with the staff we had come to love. We had a very early morning flight to Oahu and it was so hard to say goodbye to everyone. We could have moved in permanently having such luxury treatment. As we prepared for bed we noticed presents were waiting for us, including a local Hawaiian designer Tori Richard shirt hanging in Jake’s room. The thought that goes into every VIP experience at the Andaz, the compassion and warmth of the staff and the spectacular surroundings are what make the Andaz Maui my favorite resort on the island.

The next day we took a flight to Oahu for the second half of our adventure. We traveled to the North Shore of the island just in time for the Hawaiian Pro Surfing Event and we joined in the festivities along with some of the world’s best surfers while admiring the famed Banzai pipeline. We then checked into the nearby iconic Turtle Bay Resort, the only luxury resort on the North Shore and an easy 50 minute drive from Honolulu.

The resort offers five miles of spectacular ocean front royal blue waters. We checked into our lovely, upgraded beachfront cottage. There are 42 of them arranged in clusters of 6 at the water’s edge, all contained within a very private paradise away from the hotel towers. The cottage features 15-foot ceilings, Brazilian walnut floors, a Kalista deep-soaking tub and custom modern Hawaiian design.

I indulged at the 11,000sf Nalu Kinetic Spa for a tranquil massage treatment, set in a private outdoor cabana at the edge of the crashing surf. This was such a beautiful and relaxing setting. At the same time Jake had a private experience at the resorts adorable stables. The resort offers a hands-on activity for younger guests where they get to groom and saddle the horses and ponies before heading out for an hour long ride along the Kawela side of Turtle Bay. A perfect opportunity for guests interested in the hands on experience of horse lifestyle.

The cottages come with their own concierge service who brought flowered and candy leis for Jake as well as a lovely gift basket filled with local products before we headed off to a private Chef’s dinner on the lanai of the resorts Pa’akai restaurant. Overlooking the ocean, we were serenaded by one of the finest singers anywhere, Hawaiian born Kuhio Travis. Kuhio joined us at our table after his show. A stunning voice and such a rich soul.

Chef de Cuisine John Armstrong came to our table and escorted Jake down a large freight elevator into the resorts massive subterranean kitchen and Bake shop in order to prepare our custom made desserts. The public is never allowed in this area and it was such a special treat. Chef took Jake into the gigantic freezers to pick out the fresh ingredients and then led him through a course in dessert preparation for extravagant over the top banana splits. Jake was able to design the craziest concoctions, much to the joy of our fellow diners who enjoyed the procession from the kitchen to our table. Jake was in heaven.

The following morning Jake was surprised with a custom surfing lesson with resident expert and pro surfer Rocky Canon who took Jake on the board with his two famed surfing dogs Hina and Kahuna. This was Jake’s first time ever on a surf board and Rocky calmly paddled with him out to the breakers and surfed back to the beach while the excited dogs were eager for more. Locally born and raised, Rocky is an amazing guy and wonderful with all ages as he guides them comfortably into the waves. The excursion is part of the North Shore Guides Club at the resort, Canon's range of gentler standup tours to more advanced surf outings can be booked by guests of the property during a stay.

One of the benefits of staying at the Turtle Bay resort is that Paradise Helicopters operates from their property. They are the best in Oahu and also a locally owned and operated company. They can fly you to some of the most private and remote locations in Hawaii, and land! They offer the best landing spots because of their local connections that no other company can replicate. Try taking their custom MD-500 Magnum P.I. replica, complete with a special landing on top of Kualoa Ridge or experience the “Magnum” tour with stunning views of the North Shore, Pearl Harbor, Diamond Head and the sacred Kaliuwa‘a Falls.

Our final destination for our adventure is really a kid’s dream and we checked into the enormous Aulani, A Disney Resort & Spa. Not really a luxury offering, but certainly blissful for kids from around the world. 

Aulani is located on the beautiful beaches of Ko Olina on the coast of Oahu. The Resort sits on 21 oceanfront acres, at the base of lush green mountains and dark blue ocean waters. The location is about 40 minutes from the bustling tourist area of Honolulu and Waikiki Beach. With 351 rooms including 16 suites and 19 Grand Villas, the prime attraction here are the water options including the massively popular Waikohole Valley lazy river and thrilling waterslides.

We were greeted by a Disney ambassador who put more Kukui nut shell leis on Jake (he had quite a collection of these by now). We stayed in an intimate and lovely 1 bedroom suite overlooking the entire resort and the ocean beyond. The better option for families and VIPS would be in one of the three bedroom Grand Villas with 2,174 sf of space.

Our first foray the following morning was the traditional Disney Characters breakfast at Makahiki. This was an extravagant buffet filled with energy that most kids love. The local resident Aunty performs along with a few Disney characters while you eat. Jake couldn’t wait to get out of there after devouring his Disney themed pancakes to jump into the lazy river and the surrounding giant waterslides. We were hard pressed in getting him to experience much more at the resort on our second day. This really is the ultimate attraction at Aulani and the kids have an amazing waterlogged time.

We ended the vacation the following morning with an early spa treatment at the large Laniwai spa. This was a special package offered to families where they can all be together side by side and experience a Hawaiian massage that has been passed down through generations.

This ultimately was an amazing and unique experience for Jake that while often costly and above most budget travel, can be appreciated by many travelers with so many variations and packages at the various resorts. There are many custom options for every luxury traveler including those with billionaire tastes. This was a once in a lifetime experience for Jake made even more special by the amazing staff we encountered at the Andaz Maui and some special memories he will have for a lifetime.

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