Nicole sent us her reader success story to Hawaii in 2024. This was a family trip with four generations in Hawaii, and we love it so much! Here is her story:

About a year into my points and miles journey, I took my family of four to Hawaii. I fell in love with Maui’s natural beauty and rich culture and knew I wanted to return. Points and miles made it possible to successfully pull off an affordable yet luxurious four-generation trip to Maui, Hawaii. 

 

Flights

Before the Turkish Airlines award-chart devaluation in early 2024, I booked our longest flight segments on United via Turkish Airlines for 7,500 miles and $5.60 per person each way from IAH to OGG and OGG to LAX. These flights totaled 30,000 miles and $44.80 for my family of four. (These would now cost 10K points each way).

I booked positioning flights on Southwest Airlines® using a combination of miles and flight credits to get to and from our home airport in San Antonio. SAT to HOU was 7,121 miles and $27.74, then LAX to SAT was 68,992 miles and $22.40 for the four of us.

 

 

Accommodations

Airport Stay

On our 11-night adventure, we did quite a bit of hotel hopping. This started with a stay at the Best Western near Houston Hobby. The cash price for one night was $105.29 through Chase Travel℠. I was able to use my $50 credit from card_name, leaving me with a bill of only $55.29 for our airport stay. While this wasn’t a luxurious stay, it was nice having a comfortable place to sleep near the airport for a low cost. 

Vacasa Rental

I booked a three-night stay at a beautiful two-bedroom Vacasa property in the Wailea area through Wyndham for our first few nights in Maui. My Player Two had a Wyndham card that allowed us to book at a 10% discount for 81,000 points and $0 out of pocket. This Vacasa was beautifully decorated, near great shopping and beaches, had an ocean view, and offered amenities like a shared pool, barbecue grill, beach toys, and chairs. This was priced at $1,311 for three nights, but we paid $0.

 

 

 

Hyatt Regency Maui

To finish our Maui trip, we stayed at the Hyatt Regency Maui for five nights on points. I booked one night in a standard suite and four nights in a two-queen room for 148,000 points. I also applied a club access award I earned to the reservation.

Shortly before our trip, I was given a Guest of Honor award. I emailed the hotel using the Travel Mom Squad upgrade template, letting them know we would be celebrating my daughter’s sixth birthday and that we were excited to return to their resort. I was pleasantly surprised when we checked in to find that we had been upgraded to an ocean-view suite for all five nights of our stay.

 

 

The hotel provided a birthday cake, a variety of treats, and decorations celebrating my daughter’s birthday. Their thoughtful touches were so appreciated. The room was beautiful, with two lanais, a separate sleeping area and living room, and a bathroom with a rainwater shower and separate soaking tub. This would have cost $8,639 in cash (plus an estimated $150 per night for club access and $40 per night for valet parking), but it was $0 out of pocket. 

 

 

Four-Generation Stay

Four generations of family joined us for a portion of the stay in Maui. I booked them one night at the Hyatt Vacation Club next door in a two-bedroom ocean-view suite for 43,000 points. They also fell in love with Maui and enjoyed exploring the grounds and using the amenities at the Hyatt Regency and Hyatt Vacation Club properties. The biggest highlights for our group, with ages ranging from 2 years old to 74 years old, were the pools, onsite animals, beach access, and nearby shopping and restaurants at Whaler’s Village. 

 

 

LAX Stay

Before flying home to San Antonio, we stayed two nights at the Hyatt House LAX/Century Blvd on points. I booked a studio suite for two nights for 24,000 points. Upon arrival, I was upgraded to a one-bedroom suite at no additional cost. This stay would have cost over $500 but was $0 with points. 

 

Transportation

I booked our Hawaii rental car through Hertz via Autoslash. I paid $212.92 for a 9-day rental in a compact car.  We received a small upgrade and were given a Dodge Charger. By paying with the card_name, I could waive additional insurance coverage since that card offers primary rental car coverage, which provided additional savings of over $90.

On this trip, we took a handful of Lyft rides to and from airports. card_name holders receive a complimentary DoorDash Dash Pass, which can now be linked to Lyft. Lyft offers a variety of coupons for Dash Pass holders, which significantly reduced our transportation expenses on this trip. We saved $68.86 on our Lyft rides by having a Chase Sapphire Preferred® card and utilizing its benefits. 

Finally, I strategically tried to book accommodations that offered free hotel shuttles to save a little money. This included the Best Western in Houston and the Hyatt House LAX. 

 

Food

I used several methods to save money on food. We didn’t pay for a single breakfast on this 11-day trip! For our first few days in Hawaii, we had a kitchen at our Vacasa where we could take advantage of groceries to prepare meals. I used the Instacart credits (no longer available) and the $10 monthly DoorDash credits on my and my player two’s Chase Sapphire Preferred® Cards to get free food each month. I would purchase things with a long shelf life, like jerky, cereal, Pop-Tarts, nuts, dried fruit, granola bars, ramen, macaroni, chips, cookies, and more. By selecting pick-up options through DoorDash, I could avoid paying fees.

Once I had my items, I would add them to my “food suitcase” (I genuinely dedicated one of our carry-on allowances to bring an entire suitcase of food, but it gave us extra space for souvenirs later!). I brought over $150 worth of food that I received for free because of card benefits.  [Pam’s note:  We are so impressed by this, Nicole!]

This covered all of our snacks and supplemented many meals. I chose the Hyatt House LAX intentionally because of the location and offerings, but also because the room I booked had a full kitchen. One of my kids’ favorite meals was the Kraft macaroni cups (that I got for free through DoorDash) microwaved in our hotel room kitchen. 

 

Perishable Items

For perishable items, I took advantage of receipt scanning. Over about six months, I scanned receipts into the Fetch, Coin Out, and Receipt Hog apps for points. I then redeemed those points for about $40 worth of cash and Target gift cards. I used $42.36 in credits to purchase things like milk, bread, cheese, juice, fruit, vegetables, and sandwich meat. Between my DoorDash items and my receipt scanning grocery credits, I was able to buy all of my groceries for Hawaii for less than $1 out of pocket.

Having club lounge access at the Hyatt Regency Maui was a huge financial savings. My kids enjoyed choosing what they wanted off the breakfast buffet each morning and we easily made dinner out of the appetizers that were available in the evenings. It was also nice to have access to complimentary juice, sodas, and above all else—a latte machine! 

The Hyatt House also offered a complimentary breakfast, and it was nice to start the day with an assortment of foods, juice, and coffee right downstairs in the lobby. This hotel shares a building with the Hyatt Place LAX, and interestingly enough, guests at Hyatt Place who did not have Hyatt status had to pay for the breakfast buffet. If that trend continues, I would definitely book at Hyatt House if available. 

 

Airport Lounge Access

Lastly, we were able to use the four complimentary Capital One Lounge passes from our Venture cards during our layover at the Denver airport. This was a perfect break for our family with unlimited food, beverages, and desserts. We all felt so fancy!

 

Activities

For this trip, I focused mostly on planning free and low-cost activities. Beaches, which are free and public in Hawaii, were a must-see. Pools were a main activity at the hotels. We visited the Ali’i Kula Lavender Farm in the upcountry for around $20. We visited the Hawaii Wildlife Discovery Center at Whaler’s Village, which was free but accepts donations, and my daughter loved the arts and crafts station. We also took advantage of our resort fee inclusions at the Hyatt Regency (which are waived on points bookings, so these activities were truly free!) and participated in bracelet making, ukulele lessons, coconut weaving, and an outdoor movie. 

 

 

I was able to book a couple of splurges at a bargain. I had earned $115 in Capital One Cash through the Capital One shopping portal referral bonuses. We redeemed those for Groupon gift cards, which I then used to book a whale-watching tour with the Pacific Whale Foundation for my two daughters and me. For one adult, one child, and one infant, I ended up paying $17.45 out of pocket. 

 

 

Timeshare Presentation

There are timeshare presentations offered all over Hyatt Regency Maui. We opted to do a 90-minute timeshare presentation in exchange for two free adult luau tickets and 15% off a child ticket. My three-year-old was considered an infant and was free. The timeshare presentation was pretty relaxed and mostly involved sitting outside at the beautiful resort to discuss our travel habits and goals and then going on a short tour of a beautiful condo on the property.

At the luau, they gave us a tote bag, a lovely magazine about Maui, a box of chocolate-covered macadamia nuts, and upon arrival, my daughters were each given penguin stuffed animals and snacks. Our total out-of-pocket was $89.12, which was a steal for all those goodies, a tasty buffet, unlimited cocktails, and a cultural performance. Standard seating pricing for the same luau would have been over $550.

 

 

Offsetting Expenses

Even though I was able to get great savings throughout this trip, I still needed money to cover expenses that couldn’t be paid for in points and miles. To supplement my expenses without using my regular income, I earned three bank bonuses, earned one bank referral, and earned cash back from a variety of sources throughout the year, such as Rakuten, Walmart Cash, and Microsoft Shopping, for a total of $1,303.

This was enough to cover my flight taxes, rental car, transportation expenses, activities, and several restaurant meals without using my regular income. In total, this trip would have cost over $16,000, but with points, miles, and discounts, I spent about $1,600, most of which was covered with bank bonuses and cash-back rewards. [Pam’s note: Nicole, I am bowing down at your savvy savings!]

 

Bottom Line

Because of points and miles, my family and I could take our first-ever return trip to a destination and introduce some of our loved ones to the beauty and magic of Maui. This luxurious and enriching experience would not have been possible without credit card points and wonderful resources like the Travel Mom Squad! My family and I are looking forward to another trip to the incredible islands of Hawaii soon.  

 

Thanks, Nicole for your incredible four generations to Maui story – very impressive! 🙌

 

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