A Real-Life Story of Hawaii on Points, Hawaii Savings, and Smart Military Travel
When most families picture Christmas in Hawaii, they imagine a dream trip that comes with a nightmare price tag. Flights alone can cost thousands. Hotels during peak holiday weeks routinely top $800–$1,200 per night. Add in rental cars, food, and activities, and Hawaii quickly feels like a “maybe someday” destination.
But for one military family, that dream became reality—and for less than $700 out of pocket.
This is the story of how Taryn, a military spouse and one of the founders of The Military Travelers, took her family of five to Hawaii for Christmas. Their trip was 10 days, visited multiple destinations, enjoyed beachfront resorts, whale watching, national parks, and great food—all by strategically using points, miles, credits, and military benefits.
If you’re searching for Hawaii on points, Hawaii savings, or wondering if a luxury family trip to Hawaii is actually achievable, this story will show you exactly how it can be done.
Meet Taryn: Military Spouse, Mom of Three, Points Pro
Taryn is a military spouse with three young children, including an infant. Like many military families, flexibility is limited and budgets matter. Long-haul travel with small kids requires planning—not just financially, but logistically.
Instead of powering through a single, exhausting travel day from the Midwest to Hawaii, Taryn intentionally broke up the journey with stateside stops. This made travel easier on the kids and allowed the family to enjoy the journey—not just survive it.
And because so much of the trip was covered by points, Taryn could comfortably splurge where it mattered most, like booking a car service to the airport instead of juggling car seats in freezing winter weather.
Starting the Journey: Comfort Over Chaos
The trip began with a roundtrip car service to the airport, costing $158. This was roughly the same price as airport parking, but infinitely easier with multiple kids and luggage. Sometimes the best savings strategy isn’t spending less—it’s spending smart.
Stop One: Phoenix, Arizona
Taryn’s family flew into Phoenix and stayed two nights at the Tempe Mission Palms, a Hyatt property.
- Cost: 9,000 Hyatt points per night
- Total: 18,000 points
- Out-of-pocket: $0
Thanks to a Hyatt Guest of Honor (GOH) award, breakfast was fully covered for the family—an easy savings that adds up fast when feeding multiple kids.
While in Phoenix, the family rented a car using the Chase Sapphire Reserve travel credit, making the rental completely free.
This stop wasn’t just practical—it set the tone for a relaxed, enjoyable trip.
Flying to Maui: Hawaii on Points During Christmas
From Phoenix, the family continued on to Maui, one of the most sought-after—and expensive—destinations in Hawaii.
Despite traveling during peak Christmas dates, flights were booked using Southwest Airlines points.
Total Southwest points used –
188,000 Southwest points + $100.80 in taxes covered flights for four people. Their third child is an infant and flew as a lap child for $0.
Five Nights in Maui: Luxury Without the Price Tag
The family stayed five nights at the Hyatt Regency Maui, a beachfront resort that routinely costs around $1,000 per night during Christmas week.
- Cost: 29,000 points per night
- Total: 145,000 Hyatt points
- Cash paid: $0
But the real magic came from another Guest of Honor award, which granted Taryn Globalist benefits throughout the stay.
Globalist Benefits = Massive Hawaii Savings
Here’s what that meant for their family:
1. Free Parking
Self-parking normally costs $35 per day (or $40 for valet).
Savings: $175
2. Club Lounge Access
The club lounge offered:
- Full breakfast daily
- Midday snacks
- Evening hors d’oeuvres and desserts
Taryn shared:
“We felt like there was plenty of food in the evening to feed us dinner. We ate dinner there for three nights.”
Savings:
- Breakfasts: ~$450–$500
- Dinners: ~$350–$400
3. Discounted Drinks
Happy hour pricing at the pool was great—but the club lounge drinks were even cheaper. A small detail, but one that adds up quickly at a resort.
4. $100 Room Credit
Despite having a guaranteed 4 p.m. check-in, a short delay earned them a $100 credit, which covered a poolside lunch and drinks.
5. Ocean View Upgrade
The family was upgraded to an ocean-view room—worth about $1,000 per night during Christmas week.
This stay alone represents thousands of dollars in Hawaii savings.
Exploring Maui Without Overspending
Transportation on Maui was covered using Chase Sapphire Reserve travel credits. Thanks to two-player mode and multiple CSR cards, the rental car was fully paid for.
For activities, the family booked a whale watching tour through Viator. Because Taryn frequently uses Viator, she already had reward credit available.
- Out-of-pocket cost: $30
That’s it.
Military Benefits in Hawaii: Free National Parks
Military perks played a huge role in keeping costs low.
Thanks to the America the Beautiful Pass, active-duty service members and dependents receive free access to national parks.
The family visited:
- Haleakalā National Park
- Hawaiʻi Volcanoes National Park
Both parks would normally require paid admission—but for this family, entry was completely free.
Island Two: The Big Island (Hilo)
After Maui, the adventure continued with an inter-island flight to Hilo.
The family stayed two nights at the DoubleTree by Hilton Hilo. In Taryn’s words “This hotel in Hilo was okay—nothing special, but not bad. We stayed there specifically to visit the national park, which was about a 40-minute drive.”
- Cost: 50,000 Hilton points per night
- Total: 100,000 points
- Out-of-pocket: $0
Thanks to three Hilton Aspire cards between Taryn and her spouse, they had $600 in Hilton resort credits.
According to Taryn, this:
- Covered dinner both nights
- Covered lunches and breakfasts
- Allowed them to charge gift shop purchases to the room
As Diamond members (status from the Aspire card), they also received $36 per day in food and beverage credits for breakfast.
Pro tip from Taryn:
“Charge everything to the room—including tips—so it all counts toward your resort credit.”
A rental car in Hilo was again mostly covered by remaining Chase Sapphire Reserve travel credits, leaving just $21 out of pocket.
Heading Home: Smart Stopovers Save Sanity
On the way back, the family opted for another overnight stop in California rather than pushing through a long travel day.
They used a Hyatt free night award (earned through Hyatt Bingo) to stay at Hyatt Place Sacramento Airport.
Instead of renting another car, they used Uber credits from holding multiple American Express Platinum cards.
- $28 in Uber credits for transportation
- Remaining December Uber credits to cover dinner via Uber Eats
Again, comfort without unnecessary spending.
What About Food Costs in Hawaii?
If you’ve ever visited Hawaii, you know food prices can be shocking. This family barely felt it.
Taryn strategically stacked card benefits:
- Amex Platinum Resy credits for dinner in Phoenix and Maui
- OpenTable $150 dining credit in Maui
- Marriott Brilliant $25 restaurant credit for lunch
- Airport lounge access to reduce food spending while traveling
Between credits, hotel breakfasts, lounges, and resort benefits, very little food was paid for out of pocket.
Full Flight Breakdown: Hawaii on Points
Here’s the complete Southwest flight breakdown. Keep in mind, each child is a companion on one of the adults fares.
Flights:
- MCI → PHX: 5.5k points x2 + $22.40
- PHX → OGG: 59k points x2 + $22.40
- OGG → KOA: $105 – covered by flight credits + $75 Southwest Priority credit (this is no longer available after December 31 2025) ; kids paid $11.20 total as the companions.
- KOA → SMF: 15.5k points x2 + $22.40
- SMF → MCI: 14k points x2 + $22.40
Taxes were covered using Southwest gift cards purchased with Aspire credits (note: doing this removes travel insurance protections).
Total points – 188,000 Southwest points. This would have cost 376,000 (!!!) Southwest points had there not been two Southwest Companion Passes in play.
We hope this inspires you when planning your next family adventure!
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