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By: 10xT Reader Damien Boulat

The Strategy

My wife and I have found that early to mid-November, before the madness of the Thanksgiving crowds takes hold, is a wonderful time to travel. This time around, Maui was on the wish-list, so I started exploring a strategy to get us and our 2-year old son there for a relaxing 10-day vacation.

Being based in Los Angeles, there are plenty of non-stop flight options to the Hawaiian islands. As I am well above 5/24 myself, I applied and was approved for the Bank of America Alaska Airlines Visa, which at the time offered a welcome bonus of 30,000 miles, a Companion Pass fare for just taxes, and a $100 statement credit, after $2,000 in spend in the first 3 months.

Maui Hawaii using Points and Miles
All in all we made a dream vacation happen for $670 out of pocket. Had we not used points and miles strategies our cost would have been over $3300. That’s more than $2630 in savings, with minimal effort on our part (2 new credit card sign-ups and an easy booking process).

As my son is over the age of two, we needed three flights. The Companion Pass fare covered my wife and son amounting to $422 total for both, or $322 if you consider the $100 statement credit.  My own flight would need to be booked using Alaska Miles; Saver Awards are 17,500 miles each way for mainland flights to Hawaii and were easy to find for our low-season dates. That’s 35,000 miles + $11 in taxes for the round-trip, so I just needed a little bit of extra spend on the Alaska Visa to earn the miles needed. The card also gave us one-free checked bag, which for our little family was plenty, saving us another $50 roundtrip.

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As we began to look at accommodation options, we quickly realized 9-nights in Maui, can be quite expensive. Not for us 10xT Insiders us though! We had about ~40,000 leftover Ultimate Rewards points in my wife’s Chase Sapphire Reserve account, opened the previous year, but that wouldn’t be nearly enough. My wife being at 3/24 we applied for the Chase Ink Business Preferred Credit Card, offering us another 80,000 points after $5,000 spend in the first 3 months, and closer to 90,000 after our spend to reach the bonus. All in all, that put is around 130,000 UR points, which we combined into the CSR account to get the maximum 1.5 CPP valuation on the UR portal for travel bookings.

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Although we considered some of the hotel options (there are beautiful resorts from Hyatt, Marriott and Hilton), given the length of our stay and the fact we were traveling with a toddler, a condo-style property made the most sense for us to have room to spread out and take things easy.

The Luana Kai’s living room at the ground floor so our son could run out directly on the big open grass area to play.

Turns out, there are quite a few condo-style options available directly through the UR portal. Our priority being a nice view at a location convenient to the beach, we settled on Luana Kai in Kihei, booking a direct-oceanfront 1-bedroom unit. We chose to be on the ground floor so our son could run out directly on the big open grass area to play.

Maui Hawaii using Points and Miles
The Luana Kai’s Bedroom

All in all, the unit would have costs us ~$1,850 for the 9-nights, but we paid nothing out of pocket by using ~123,500 UR points. The rate we booked was inclusive of a cleaning fee so that was covered as well.

The only thing left was a car rental. I did have a few UR points left, but after comparing with rates on AutoSlash, I determined the portal rates were not competitive and chose to save my points for future travel. We paid $337 total out of pocket for the duration of the trip and the Chase Sapphire Reserve we used for the booking provided us with our insurance needs.

The Trip

We kicked off our trip nicely with a quick breakfast visit to the Alaska lounge at LAX before boarding our 7:00 AM flight. We hadn’t necessarily planned a visit but security was a breeze and the gate was right next door, so we had time to take advantage of our Priority Pass access provided through the Chase Sapphire Reserve. Me and my wife enjoyed a couple of blueberry scones and coffee, while my son had a pancake.

We touched down at OGG perhaps 15 minutes before our scheduled 11:00 AM local time arrival and were into our rental car before noon. After being awake the whole flight, our toddler dosed off in the car, and my wife and I felt a feeling of instant relaxation as we cruised past the gorgeous tropical landscape on our way to the sunny South side of the island.

Maui Hawaii using Points and Miles
A couple of the furnishings were a tad dated but nothing could really detract from the gorgeous, unobstructed view onto the Pacific Ocean and West Maui.

Kihei, while not as luxurious as neighboring Wailea, has a wonderful small beach-town vibe and every convenience you could need so we felt at home right away. We gave a quick call to Luana Kai, who graciously informed us that our unit would be ready for us around 2 PM.

The condo was pleasantly spacious compared to a hotel room, and very clean. A couple of the furnishings were a tad dated but nothing could really detract from the gorgeous, unobstructed view onto the Pacific Ocean and West Maui. Our sliding glass door opened up to a huge open grass area before reaching the sand, a perfect space for our son to spend out his boundless energy (and boy, did he take advantage of it). A fully stocked kitchen, as well as BBQ grills next to a sparkling clean pool were the icing on the cake at this very relaxed yet well-managed property.

After a good night’s rest, it was on to our adventures, of which we had many. From swimming with sea turtles, to hiking the Iao valley, and the Luau at the Grand Wailea, we created memories that we will forever cherish. Not to mention, pounds of the freshest poke, and perhaps one too many Mai Tais from our sunset-facing deck.

The late flight back home was certainly bittersweet (although uneventful) but we know we will be back to Hawaii soon to explore another island!

We’re thrilled that, armed with a little bit of knowledge of points, miles and credit card strategies, we were able to craft a trip that suited our specific needs as a young family on a modest budget. We hope it inspires a few of you to do so as well. Cheers!

Damien Boulat,
Long Beach, CA

P.S. Bryce here. You see those cool 10xT shirts that Damien is rocking in this article? We are now giving those away to anyone who is willing to take them on their trip and write a success story about it. Email me ([email protected]) if you are interested!

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Editors Note: Opinions expressed here are author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

About the Author

Bryce Conway is the Founder of and Author of Takeoff: How to Travel the World for Next to Nothing and How to Fix Your Credit: Do it Once. Do it Right. Get on with Your Life. Bryce’s work has been featured in multiple national media outlets including Good Morning America, Money Magazine, and ABC Nightline News. Bryce created 10xTravel in 2014 and has been hanging out in the points and miles community since 2011....

Learn More About Bryce

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