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Family Travel / Humor

“I’M GOING TO MAUI!”–When you win your dream vacation

“I’M GOING TO MAUI!”–When you win your dream vacation

A funny thing happened four years ago when I was selected as the grand prize winner of Microsoft Office’s nationwide contest to be their accredited blogger at the 2010 Vancouver Games: I started to think like a winner.

B.O. (Before Olympics), my contest batting average stunk. When I’d enter to win something, I’d just assume I wouldn’t win and I never did.

A.O. (Après Olympics) when I’d enter to win something, I’d assume I would win.

I’d like to call this a winning mentality but here’s the thing: I haven’t won anything since then so I have been more of a one-hit wonder, “I-think-I’m-a-winner-but-have-loser-tendencies-type person.”

Until last week.

Hawaii has been at the top of my bucket list for several years. So when I heard about a luncheon at the Oxford  Hotel hosted by the Maui Convention and Visitor’s Bureau, I resolved to finally start planning my family’s future vacation. A girl can dream, right?

Upon check-in, we dropped our business cards into a raffle drawing and then briefly met with various tourism reps in a speed dating format. I became convinced that Maui was the perfect island for my family with its combination of scenic natural wonders, Hawaiian culture and idyllic mountain and beach adventures.

As I prepared to leave, Kelii Brown, Director of Public Relations and Promotions at the Maui Visitors & Convention Bureau, announced he was going to do the drawing for the grand-prize giveaway: two round-trip airline tickets, six nights lodging (two nights each at the Kaanapali Beach Hotel, Hotel Moloka’i, and the Fairmont Kea Lani) and a rental car.

I loudly quipped “Just to warn you, I dropped 10 business cards into the bucket.”

Five seconds later, they announced my name. In an out-of-body moment, I panicked, retracted with “Just kidding, totally legit here!”

I instinctively jumped up like I was the next contestant on the Price is Right, but Kelii (who has zero resemblance to Bob Barker or Drew Carey) did not make any indication it was appropriate to maul him. So, in a Mary Katherine Gallagher “Superstar” moment, I lunged forward and shouted:


The organizers said it was their best reaction yet. I’m sure my fellow attendees who had not won thought otherwise.

On a funny sidenote: The only time I’ve ever been to Hawaii was when I was five and my dad won a trip from a raffle at work. It’s about time something ran in the family other than big feet and crappy eyesight.

My husband was, of course, thrilled at the news and we quickly decided to bring our kids along because they are dying to go to Hawaii. We figured even with that additional cost (the trip is only for two people) along with paying the taxes, food and activities, it will be so worth it. We also decided to tack on two extra nights at Napili Kai Beach Resort.

To surprise the kids, we concocted a treasure hunt with the final clue leading them to my son’s (messy) bedroom where I had set out his tropical swim suit and Hawaiian shirt. Their reaction at the news?

(Celebratory chokehold did not cause permanent damage)

Celebratory chokehold did not cause permanent damage

Note: It became slightly less enthusiastic when we announced most of our Christmas money would go toward paying for them to come on the trip but we all feel lucky and extremely blessed.

Now, excuse me while I go buy a lottery ticket.


What activities, beaches, hikes, hotels and food do you recommend on Maui and Molokai? On my bucket list: to take my first surfing lesson, go whale watching, take the kids snorkeling for the first time, drive the Hāna Highway, go to a luau, swim with the sea turtles, hike and swim in a waterfall, visit a pineapple plantation, climb to Haleakala National Park and of course, enjoy plenty of beach time. And stay tuned for details of our adventures after our February trip.


Amber Johnson
Author: Amber Johnson

Amber is the founder and editor of Mile High Mamas, travel writer and former columnist for The Denver Post. She is a passionate community builder and loves the outdoors. She has two awesome teens and is happily married to a man obsessed with growing The Great Pumpkin.

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Amber is the founder and editor of Mile High Mamas, travel writer and former columnist for The Denver Post. She is a passionate community builder and loves the outdoors. She has two awesome teens and is happily married to a man obsessed with growing The Great Pumpkin.


  1. Awesome! Enjoy your trip!

  2. Thanks so much. Can’t wait!

  3. SO COOL!

    Your list of “must-dos” is pretty long, so I also suggest napping on the beach, reading some books and eating at Mama’s Fish House. Not only does Mama’s have the BEST food ever, but they’ve got an amazing kids meal, with traditional Hawaiian and seafood fare. It’s spendy for adults, but the kids’ menu is quite reasonable! Don’t miss it!

    We’ve been to Maui three times — just like you — never on our own dime (I also have big feet, crappy eyesight and good luck!). Our absolute favorite adventure: hiking in the Bamboo forests at the lower reaches of Haleakala National Park. Here’s a link if you want to read more:

    Just be prepared. The road to Hana can make anyone car sick. And, don’t miss the shave ice!


  4. Congratulations! I will have to try that Jedi reverse-thinking mind-trick too :).

    I was lucky enough to go to Maui years ago with my then boyfriend. I would definitely check out the Seven Pools off the Hana Highway, and maybe take in some horseback riding, which we did at the Hana Resort. Be safe and have fun! Kathleen

  5. Kristen–We have a carsick-prone daughter but I told my husband we HAVE to go to Hana. So we’ll be investigating some meds that don’t make her sleepy.

    Checking out the link now…great recommendation!

  6. You should definitely go biking down the Haleakala crater! And also do a helicopter tour of the island. Shopping in Whaler’s Village. Get some Hula Pie at Leilani’s on the Beach.

  7. Kathleen–Wonderful suggestions, thank you!

  8. Jennifer–You had me at Hula Pie.

  9. That is awesome! Go to Merriman’s in Kapalua – to die for restaurant!


    Apparently the other place, Kimos, also has great Hula Pie. It’s a yummy, towering, Maui dessert!

  11. Yummy, towering Maui dessert. LOVE local food recommendations. So often I get to a destination and have thoroughly researched our activities but not restaurants.

  12. Anna–bookmarking Merriman’s in Kapalua right now!

  13. I got married in Maui! I highly recommend staying for a night on the Hana side of the island if at all possible. The road frankly isn’t any worse than some of our mountain roads but it can be slow going and there are so many awesome waterfalls right off the highway that you want have time to explore. Plus the red sand beach on that side of the island has awesome snorkeling and since it requires a bit of a hike, isn’t very crowded. The is also a state park on that side of e island with black sand and lava tubes. I am a bit of a foodie and I was underwhelmed by Merrimans. It was fine but for the price I expected spectacular. We tend to eat at a lot of local casual places but for a splurge meal, Mama’s Fish house gets my vote! Great views too. Have fun! We love Maui!,

  14. Pineapple and sugarcane fields!

  15. When are you going?? We are going in January. Haleakala the volcano. We did a zip line. You can bike ride to the bottom if you are adventurous. Go during whale season!! It is a must must see. the road to hana is great. I love maui!! Congrats

  16. There pretty much aren’t any sugarcane fields anymore. You have drive the road to Hana, see the sun rise from top of Haleakala, splurge at Mama’s fish house, and snorkel or dive as much as possible. And get this guide book

  17. Go to the pineapple plantation & eat the pineapple ice cream. (I still dream about that, 12 years later) go to the top of the volcano – bring a sweatshirt. You might enjoy biking it. Snorkeling is fun. There is a fabulous restaraunt right on the beach that is amazing (starts with a k). Go see the monolith. Skip the hospital. It is not fun, the rooms are shared & they kick visitors out at 8… Although the stories from the old man about the attack on Pearl Harbor were pretty cool. Have fun!

  18. So happy for you, Amber! You’ll have so much fun! Agree with Steven – the road to Hana is gorgeous and will take you all day. Stop at all the waterfalls & fruit stands along the way to the 7 sacred pools! Top of the volcano is near too. But, yeah, don’t take the kids!

  19. Enjoy. Never been to Maui. We love The Big Island. Food is very expensive. Checkout for tips and advice.

  20. K. Now I want to go to Hawaii. I have never been. We plan on taking the whole family in June. BTW did I tell u I got a job working for JetBlue? So we can fly anywhere for very little on standby.

  21. Michelle–I’ve started looking at properties on the Hana side. It sounds wonderful. And I’m more a fan of smaller, local restaurants with amazing food!

  22. Vikki–We hope to go in February. THinking that will still be whale season?

  23. Steve–Ordered the book. Great recommendation! I do a lot of research online these days but it’s always nice to have a guide book you can easily access.

  24. Kassie–As a kid, I still remember the pineapple plantation we visited. The thought of pineapple ice cream will lure me there. 🙂

  25. Chris–Waterfalls, fruit stands. Doesn’t get better than that!

  26. Such awesome memories! Here’s a column I wrote when I tried to be a travel writer after visiting Maui:…/Maui–Paradise-found.html…

  27. You must must bike down Haleakala. You will love.

  28. For Hana, consider going with a helicopter company. They drive you over and fly you back. If Jamie is the driver, he will especially appreciate the suggestion. There are so many places to stop on the way. These guys know which stops are great and which are for Maui Wowie.

    Shaka Pizza in Kihea!

    A Zodiac is much more intimate than bigger snorkel boats out to Molokini. I think your kids are old enough. But ask about that, too.

    Oh, and Costco by the airport. Stop there first for beverages, snacks, and even sushi! Most prices are same as we pay here, not island prices.

  29. Like Tami said, we were able to get the Kama’aina card at the regular grocery store, so our groceries were no different than Denver prices. (We’re not costco members, so that’s an option, too.) A clerk asked us if we had one. We were honest and said no. She said she’d just put our info in the system and we gave our 303-area code phone number, and it took it! BONUS.

  30. Oh, and one of the best guide books for the islands is “The Blue Book.” It has great tips. I bet you know some other people that might be able to steer you in a direction, too.

  31. Jody–hilarious and that is exactly the way I write, too. Top 5 things to do lists are quick and easy but not entertaining/good writing. THAT is a great piece of journalism.

  32. Tami and Kara–fantastic suggestions. Would’ve have ever thought of Costco but simply brilliant. We have a collapsible cooler I’ll have to bring.

  33. JoAnn-wondering how to get said Kama’aina card?

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