Mommy Points: Booking Almost 3 Weeks in Hawaii With Miles, Points and a Family

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I'm prone to getting some weird ideas at times, especially in the travel department. You know, those ideas that sound great in the abstract, but look somewhat horrific in the light of day with real-world realities sprinkled throughout. I've gotten decent at squashing those out-there ideas before we get too far in the process, but this year I followed through with a "harebrained idea." I wanted to spend most of June with my girls in Hawaii. But, we weren't going to just stay put the whole time -- we were going to explore three different islands. Part of the time grandparents would join us, part of the time my husband would join us and for a portion the girls and I would be on our own. Oh, and I'd need to work some while we were there. Grand plan or impending disaster?

In total, it would amount to 14 hotels, 21 days away from home, three Hawaiian Islands, two West Coast states and a whole bunch of spent miles, points and cash. The first three nights and hotels happened before the girls joined me on the West Coast due to the opening of Star Wars: Galaxy's Edge at Disneyland falling right in front of this trip, so only I experienced that first frenzied part of the trip. But, if you want to tack Disneyland onto your Hawaii trip as I did, here's one of those hotel reviews.

From Disney in Anaheim, I took Amtrak (for less than $40) down south to San Diego and met up with my parents and my kids who had journeyed together from Texas to start the shared adventure. While I don't necessarily recommend most families mimic the pace of this trip, I don't regret a minute of it either. We saw and did a lot for the first two-thirds of the trip and then slowed the pace down and relaxed at two full-service Hawaiian resorts for the final week.

In the interest of full disclosure, know that while all of the points, miles and upgrades spent were my family's, some of the cash elements were paid for by TPG for reviews, content, etc. None of the trip was sponsored or comped or known by any of the hotels/airlines.

Why So Many Hotels and Islands?

In Hawaii we stayed in 11 hotels and hopped to three islands, visiting Oahu at both the start and the end for an effective total of four islands if you count that one twice. It sounds a little nuts, but it didn't feel that crazy. A small element of the repeated lodging changes was done simply to check out more hotels, but mostly it was done because my parents travel fast, we wanted to see and do a lot and we slept close to the activities we planned for the day. Hawaii may not sound very big, but it can easily be an hour or two each direction to do things that are relatively "nearby." Spending at least four hours round-trip in the car to go from Kona to Volcanoes National Park and back doesn't sound fun, so we just changed where we slept many nights as we traveled around to avoid backtracking.

My parents (Grandma and Grandpa Points) also went into this trip assuming it would be their one and only trip to Hawaii, so we wanted to give them the highlights of a few islands. Turns out, they loved it so much, they haven't ruled out a repeat visit. With that background, here's how we did it with miles, points and cash and some elite status perks.

Starting in San Diego

Homewood Suites By Hilton San Diego Airport - Liberty Station: Two-bedroom suite for us and grandparents, $300 cash (standard rooms available for 60,000 Hilton points per night).

Hawaiian Airlines Flight to Honolulu: Booked and upgraded with cash. First class one-way flights from the West Coast to Hawaii start at around $600 with cash or 40,000 Hawaiian miles.

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Mommy Points Thoughts: Overnighting on the West Coast before heading to Hawaii is, by far, my favorite way to travel to Hawaii with kids. Upgrading our relatively cheap cash tickets on Hawaiian was an out-of-pocket splurge, but if this was going to be a "once in a lifetime" trip to Hawaii for my folks, I wanted it to be as special (and comfortable) as possible. The Hilton San Diego Liberty Airport was nothing particularly special itself, but there are affordable food options in its shared parking lot and a free shuttle to and from the nearby San Diego airport. I'd stay there again under similar circumstances if the price was right, but don't recommend it for a longer term stay.

Overnight on Oahu

Westin Moana Surfrider in Waikiki: Two rooms, $255 each using AAA rate + taxes and resort fee (standard rooms bookable for 60,000 Marriott points per night)

• Free breakfast with Marriott Platinum status (in fact, it was one of the best Marriott Platinum breakfasts I've had anywhere!)
• Included lounge access

Southwest Airlines Flight Honolulu to Kona: 2,100 Rapid Rewards points each

Related: Best Credit Cards for Southwest Airlines

Mommy Points Thoughts: We only stopped for the night in Honolulu so my parents could visit Pearl Harbor (even though the USS Arizona is "closed"). I knew my mom would love the history and plantation vibes from the Moana Surfrider, but if all we needed was a bed for the night, I probably would have just spent 12,000 Hyatt points or a Hyatt Category 1–4 award from the World of Hyatt Credit Card to stay at the Hyatt Place Waikiki. I don't love Waikiki in general, but hiking Diamond Head was a real highlight of this first part of the trip for us -- my 9-year-old loved being old enough to do "big kid things" with us while her sister rested with Grandma at the hotel. Here's how we saved an hour at the Honolulu Airport on this leg of the trip.

5 Nights on the Big Island

Sheraton Kona: Two rooms for two nights at old SPG cash and points rate of 15,000 Marriott points + $75 per night

• Free breakfast with Marriott Platinum status
• Lounge access that we turned into dinner

Cabin in Volcanoes National Park: Two cabins booked via Volcano House, $90 per cabin. (Coded as travel for 3x points on my Chase Sapphire Reserve).

• Note that these cabins have no air conditioning, Wi-Fi or private plumbing. You can book a "normal" hotel room at Volcano House for $250–$300.
• Entrance to Volcanoes National Park was free thanks to Grandpa's lifetime America the Beautiful Senior Pass. Having a 4th grader would have also gotten us in for free.

Hilton Grand Naniloa Double Tree in Hilo: Two rooms, 50,000 Hilton points per night

• Waived parking/resort fee when using points. Lots of inclusions from Hilton Gold status -- including a box of Hawaiian chocolates.

Hilton Waikoloa Village Resort: Two rooms, 60,000 Hilton points per night.

Related: Best Hilton Credit Card for Family Vacations

• Free breakfast with Hilton Gold status from the Hilton Honors American Express Ascend Card.

Hawaiian Airlines Flight from Kona to Lihue: Booked one ticket with 7k United miles, the rest with cash as availability was poor.

Mommy Points Thoughts: We drove 500 miles in our rental car around the Big Island (booked via Costco Travel) and it was a joy to see a diverse new-to-me island. This part of the trip made me glad we lugged our own car seat along for the ride (the Cosco Scenera Next) as we sure did use it -- a lot.

After the recent eruptions subsided, you can no longer see flowing lava in Volcanoes National Park, but it was a majestic place all the same. Staying within the park for a night was a great choice, but I'm glad we only "camped" in the cabin without our own running water and Wi-Fi for a night. I recommend taking a free ranger hike -- both kids were able to keep up and loved it. The Grand Naniloa about 40 minutes away in Hilo was a treat with no added fees on our stay (especially after staying in a cabin the night before). The Hilton Waikoloa Village back on the Kona side of the island was so massive it had its own tram system -- we will return there for sure for a longer vacation. If you like coffee, be sure and visit a coffee farm or two while in Kona -- we enjoyed Greenwell Farms.

7 Nights on Kauai

Westin Princeville Resort: Two-bedroom unit, two nights at $600 per night with AAA discount (standard rooms are 60k Marriott points per night).

• Free (very limited) continental breakfast with Marriott Platinum status.
• You can book a longer stay for less with a targeted vacation club offer -- great deal if you can get it. Costco Travel also has some discounted vacation packages to this resort.

Marriott Courtyard Kauai at Coconut Beach: Two rooms, 25,000 Marriott points per night

• Free breakfast with Marriott Platinum status
• Waived resort fee with Platinum status

Grand Hyatt Kauai, Four nights at 25,000 Hyatt points per night, one room for grandparents with club access at 33,000 Hyatt points for their one night. (Hyatt Explorist certificate used for lounge access on our four-night room reservation.)

• Ate breakfast in the lounge each day
• Ate dinner in the lounge some of the nights
• No resort fee on award stays

Hawaiian Airlines Flight to Honolulu: Booked with cash due to low fares ($59/each)

Mommy Points Thoughts: While the Big Island was a great adventure, Kauai is always my favorite part of a trip to Hawaii. From Hanalei Bay, to shave ice in Princeville, the Smith Family Luau and exploring Waimea Canyon, Kauai is special. With the St. Regis Princeville Resort now rebranded as just the Princeville Resort, the Westin Princeville Villas is your best points bet on the north side of the island. The best news of all for us at this part in the trip was that there were two sets of washers and dryers in our suite at the Westin!

The Marriott Courtyard Kauai is under serious renovation, but the rooms are finished and a good value for 25k points per night if all you need is a place to sleep. But, the crown jewel of the family travel points world is the Grand Hyatt Kauai. We loved our third stay here, and wouldn't hesitate to use points to book a fourth stay in the future. Stay tuned for a full review in the coming weeks.

3 Nights on Oahu

Aulani, Disney Resort and Spa: Booked for 20% awards return using the Capital One Venture Rewards Credit Card via Hotels.com (offer available until Jan. 31, 2020), $600 per night, no resort fee

• If you can find availability, booking Aulani via rented Disney Vacation Club points using David’s Vacation Club Rentals could easily save you 50% off the retail price and is by far the best way to book your stay from a cost perspective.
• Discounts for Disney annual pass holders and more are available at Aulani certain times of the year, but not usually during peak summer dates.
• Stay tuned for this review as my opinion on the resort swung almost 180 degrees from the first to last day of the stay -- the only time that happened on this trip.

Alaska Airlines Flight to Seattle: We used the annual companion voucher from the Alaska Airlines Visa Signature® credit card plus an old upgrade from an Alaska Airlines status match. This allowed us to save money and fly upfront.

Sleeping in Seattle

Radisson Seattle Airport: Booked for 38,000 Radisson Rewards points

Second leg of the Alaska Airlines itinerary, Seattle to home in Houston.

Mommy Points Thoughts: I'll save my thoughts on Disney's Aulani for its own separate review to come soon, but know that if you don't want to spend $500–$600 per night, you should really try to book via rented Disney Vacation Club points as rates then start at just $289 per night via David’s. Going home to Houston via a Seattle overnight worked out beautifully and the Radisson Seattle Airport's renovated rooms were great. The lobby is still under construction and the shuttle bus was very slow, but the hotel is actually in walking distance to the airport.

Bottom Line

For the seven total travelers, we utilized five different airlines, four hotel chains, two non-branded stays and three rental car companies. The trip cost over 500,000 miles and points and several thousand dollars in cash, especially when you factor in some flights for my parents and husband that weren't specifically mentioned here. It wasn't cheap, it wasn't free, but I'll be cliche and call it priceless. While we could have, we didn't pay for all of our expenses with miles and points when it didn't make sense, but miles and points easily knocked thousands of dollars off the grand total. At the Grand Hyatt Kauai alone, Club Level rooms sell for $700–$800 per night in the summer and we had a total of five nights in those rooms without spending a penny of cash.

But this trip wasn't really about the hotel rooms (though some days it was about the hotel pools). This trip was mostly about Hawaii's waterfalls, the shave ice, the volcanoes, vistas, the ocean, the beaches, the coast, the foliage, the adventure and family memories. In all of those ways, the trip gets a resounding A+ from all of us. Stay tuned for more Hawaii destination guides and hotel reviews rolling out over the next several weeks.

All images by author.