If I Won the $4,500 Sweepstakes Prize, I’d Return to My All-Time Favorite Destination With the Kids

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Jasmin:   Have you checked out our biggest-ever travel sweepstakes yet?  We’re giving away a dream trip valued at up to $4,500 to a lucky reader!  Just head over to our travel sweepstakes page and complete the steps to enter by May 31, 2018.

While none of us on the Million Mile Secrets team are eligible for the prize, we’ve been imagining all the cool places we’d go if we won $4,500 to travel.  The kids and I have a ton of adventurous, off-the-beaten-path spots on our bucket list, so picking just one is tricky.

But I’ll be honest, right now nothing sounds better than relaxing in the tropics with a Mai Tai in one hand and a good book in the other.  If we could get away, we’d return to a destination that holds a special place in my heart:   Hawaii.

Travel Sweepstakes Id Escape To My Favorite Destination
Mommy Needs a Mai Tai – This One From the Hilton Hawaiian Village in Honolulu Was on Point!

If you’re the winner of our travel sweepstakes, maybe you’ll consider Hawaii, too.  But if not, there are plenty of ways to get there cheaply with credit card miles and points!

What I’d Do With the Travel Sweepstakes $4,500 Prize

Link:   Million Mile Secrets Travel Sweepstakes

I get sentimental when I think of Hawaii, because it was the favorite vacation spot for my family when I was growing up.  And since my first visit at age 4, I’ve been lucky to visit the Aloha State over a dozen times either on airline employee passes or using miles and points.

I’d go back in a heartbeat and never get bored – there are so many awesome things to see and do.  Between the vibe, the culture, the incredible food, and the amazing views, it’s truly a magical spot.  When you get off the plane, even the air smells different.

Travel Sweepstakes Id Escape To My Favorite Destination
Wayback Playback – That’s Me in the 1970s Paddling Around in Honolulu (I Believe This Is at the Former Kahala Hilton)

My last trip was to Kauai for a friend’s wedding – without the kids.  Before that, we visited when my daughters were 2 and 3 years old and I was pregnant with my son.  He’s still a little miffed that he hasn’t “officially” gone, although the girls tease him about actually having been there as a fetus.  🙂

A trip to Hawaii with a toddler and preschooler is far different from the kind of vacation we’d plan now.  My son would love to take surfing lessons and check out Pearl Harbor for the submarine tour and aviation museum.  The girls, meanwhile, are all about the beach, snorkeling, and shopping.

Travel Sweepstakes Id Escape To My Favorite Destination
We’d Definitely Return to Hanauma Bay for the Incredible Snorkeling and Calm Water

On our next visit, I’d like to take the kids to Maui or Kauai as well.  They’d love watching the sunrise from the Haleakala volcano (or maybe taking a bike ride down?) or hopping on a catamaran for a cruise along the Na Pali coast.

How to Fly to Hawaii for Cheap

Link:   Best Airline Credit Cards

Getting to Hawaii on paid tickets can actually be reasonable when there’s a fare sale.  Recently, we’ve seen prices in the mid-$300 range from the mainland US, and these promotions seem to come around fairly often.  There’s also a lot of excitement about Southwest starting flights to Hawaii in late 2018 or early 2019.

So if you win our $4,500 travel sweepstakes, airfare won’t necessarily make a huge dent in your prize money!

When fares are this low, it could actually make the most sense to redeem flexible points for paid tickets, like through the Chase Ultimate Rewards travel portal.  Depending on the card you have, you could spend fewer points than you would on an award ticket.  And when you book this way, there are no blackout dates.

For example, folks with the Chase Sapphire Reserve get a value of 1.5 cents per point when they book travel through the portal.  So a $350 ticket would cost just ~23,333 Chase Ultimate Rewards points, plus you’d earn airline miles for the flight.  That’s probably the angle I’ll take when we go, if I can find a cheap deal.

Travel Sweepstakes Id Escape To My Favorite Destination
Consider Redeeming Flexible Points for Paid Tickets When Airfare to Hawaii Is Cheap – You Could Save Points!

Otherwise, there are plenty of options to redeem miles and points for award flights to Hawaii, and there are especially good deals for folks on the West Coast.  Here are some of the cheapest round-trip flights from the Mainland US in coach:

Remember, you can transfer flexible points if you don’t have enough airline miles in your account.  Here’s a handy chart showing which points transfer to which airlines.

Splurge on Activities and Food, Not a Hotel

Link:   Best Hotel Credit Cards

Hotels in Hawaii can be very pricey, especially at fancy beachfront resorts.  In peak season, you’re looking at hundreds of dollars a night.  Some folks consider Airbnbs to save money on accommodations and food.

I’d much rather redeem points for award nights (which can be a tremendous value here) and save my pennies for fun meals and activities like luaus and sunset cruises!  Hawaii’s also home to some of the most amazing sushi I’ve ever had (highly recommend Sansei – kid you not, I still dream of their Panko Crusted Fresh Ahi Sashimi – so good).

For example, on my most recent visit, I used Hyatt points to stay at the Grand Hyatt Kauai.  What a gorgeous resort!  My only regret is that the kids weren’t along for the trip (there’s even a lazy river pool and waterslide), so that just means we’ll have to go back.

Travel Sweepstakes Id Escape To My Favorite Destination
It’s Really as Spectacular as It Looks. I Can’t Wait to Take the Kids to the Grand Hyatt Kauai

Rates for standard rooms here are often over $700 per night including taxes.  But you’ll only redeem 25,000 Hyatt points per night and won’t pay resort fees!

If you earned the 40,000 Hyatt point sign-up bonus from The Hyatt Credit card, plus factored in points from meeting minimum spending and adding an authorized user, you’d have nearly enough for 2 free nights at the Grand Hyatt Kauai.  I’ve kept this card for many years because of the complimentary free night at a category 1 to 4 Hyatt each card anniversary and automatic elite status.

And you could boost your Hyatt point balance even further by transferring Chase Ultimate Rewards points to Hyatt from cards like the Chase Sapphire Reserve, Chase Sapphire Preferred Card, or Chase Ink Business Preferred Credit Card.

If you’re looking to book award nights in Hawaii, I’d suggest first checking Hotel Hustle to find locations you can book with points in areas you’re interested in.  Then, when you have a hotel chain in mind, check out our post on the best hotel credit cards to figure out the easiest way to earn points for your trip.

Of course, if you win the travel sweepstakes, you could treat yourself to any hotel you like!

Bottom Line

I admit I’ll be a little envious of the lucky reader who wins our $4,500 travel sweepstakes.  But it’s been fun to fantasize about where I’d take the kids if we were eligible to win.

Although we’ve been before, I’d love to go back to Hawaii for an epic getaway using miles and points.  Now that they’re older, they’ll much better appreciate all the wonderful things the islands have to offer.  I can already picture my son on a surfboard flashing the “hang loose” (shaka) sign!

Even if you don’t end up winning the prize, there are still plenty of options to visit Hawaii for free or really cheap.  Check out the best airline credit cards and best hotel credit cards for easy ways to collect miles and points for your dream trip.

Where would you go in Hawaii?  Any must-do suggestions for kids I’ve missed?

Jasmin Baron is a contributor to Million Mile Secrets, she covers topics on points and miles, credit cards, airlines, hotels, and general travel.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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