This past May, my family of four went to Hawaii with my mom and aunt. We used points and miles to pay for our hotels, rental cars, and flights. It was an epic outdoor adventure!

Flights / Transportation: I booked a set of one-way flights for this trip. We flew KC to Maui, Maui to Kona, and Kona to KC. While on the Big Island, my husband and son flew to Honolulu for the day to visit Pearl Harbor. My son is a huge history buff; this day was an absolute bucket list day for him. All made possible by points! 

Taxes and fees for our flights for six came in at just over $100. My husband, myself, and my mom hold Southwest Companion Passes, which significantly decreased the number of Southwest miles we needed for the trip since we didn’t need any miles for my daughter, son, and aunt to fly. Then, my husband and son flew to Honolulu for the day, which was $22.40 for the roundtrip flight. 

My Chase Sapphire Card gives me access to the Chase Travel Portal. I used Chase Ultimate Rewards to book our minivan for Maui and the Big Island. This was a great use of points for our family since the minivan rentals would have been close to $2,000 for ten days. 

Always use a credit card with excellent rental car collision coverage when booking rental cars, even with points. This allows you to decline extra coverage, and if you do get into a collision, you can turn it into the credit card company instead of your car insurance. (Be sure to check with the credit card company since I am not an insurance expert.) 

Stay: We stayed at the Hyatt Regency Maui and Hilton Waikoloa. 

For the Hyatt Regency Maui, I transferred points earned from my Chase Business Ink Cash $0 annual fee card and Chase Freedom Flex $0 annual card to Hyatt for this stay. This was made possible since I hold the Chase Sapphire Preferred Card that gives me access to 14 incredible transfer partners, including Hyatt. 

While at the Hyatt Regency Maui, we were complimentary upgraded to two queen beds and oceanfront balcony rooms! Oh my gosh, it made our stay!

I used Hyatt Regency Club passes that I earned from staying a specific number of nights with Hyatt, which significantly offset the cost of food for our stay! The Regency Club had a daily offering of breakfast, mid-day refreshments and snacks, hors d’oeuvres, and desserts in the evening.

We loved the Hyatt Regency Maui. I could talk about it all day! They greet you with the most beautiful lei when you arrive. There is a colossal waterslide my son went down about 100 times. We also attended a lei-making class at one of the complimentary classes for kids on the property. 

Pro tip! When you book through Hyatt with points, you don’t have to pay the daily resort fee of $45 plus tax added to your nightly rate and each room of your stay when paying cash for a stay at Hyatt Regency Maui.

The Hilton Waikoloa Village was booked with Hilton points earned through American Express personal and business Hilton co-branded cards. Due to Chase’s 5/24 Rule, open business cards over personal cards whenever it makes sense for you. 

The Hilton Waikoloa Village is massive! It has an entirely different feel than the Hyatt Regency Maui, and I was a little shocked when we first arrived at how different it felt. There is a monorail to take you from one end of the resort to the other.

My kids loved it. There are so many pools, waterslides, restaurants, and a lagoon. The lagoon was my favorite part. It allowed my children to snorkel in calm waters, and they saw tons of fish and sea turtles. We also rented paddle boards for a few hours; they had the best time. 

Fun: We spent so much time hiking and snorkeling on this trip. Below is a list of trails and snorkel spots we did while in Hawaii

Maui

• Haleakala National Park- We loved the Pipi trail and Halemau’u Trail
• We drove the entirety of the Road to Hana. If you plan to do this, go early! Like, super early! It just gets more congested as the day goes on.
• Wai`änapanapa Hawaii Black Sand Beach 
• I could not get sunrise reservations to Haleakala Summit through recreation.gov, but I have heard it is incredible.
• When we return to Maui, I want to spend more time near Paia! It looked beautiful as we passed through.

Big Island

• Waipio Valley Lookout 
• Pololu Valley Lookout – Locals at the trailhead tell visitors how to visit respectfully and safely. This trail is steep up and down, and when you get to the bottom, it is a spiritual experience! 
• Kaloko-Honokohau National Historical Park- Fantastic little hidden beach with so many sea turtles! Go early in the day while the tide is calmer. You can park at a marina for a shorter walk.
• Kahala’u Beach Park – This little city park doesn’t do it justice when you pull up, but once you put your head underwater, you know why it comes highly recommended! 
• Punalu’u Black Sand Beach 
• Papakōlea Green Sand Beach- It is a long walk but worth it. Take plenty of water, sunscreen, and snacks. It is truly a hidden green sand beach! Gorgeous! 
• Volcano National Park- The entire time we were in Volcano National Park, it felt like we were in the scenes from Jurassic Park. I planned too much for this day, and we were tired when we got to the park. Here are the short/easy hikes we did. Thurston Lava Tube 1 mile, Pu’uloa Petroglyphs, Devastation Trail 1 mile, and be sure to lava view at night.

Eat:

While at the Hyatt Regency Maui, we attended the Drums of the Pacific Lu’au. It was expensive and worth every dime. We also hit up Ululani’s Hawaiian Shave Ice and ‘Ūmalu, the poolside bar, a couple of times. The most adorable little pie shop, Leoda’s, is on Maui. They have a food menu, but we partook in pies.

On the Big Island, we did a Target pickup when we first arrived for some breakfast and quick lunch items and snacks. Our room had a mini fridge and a microwave on every floor. 

My husband did try some of Hawaii’s famous gas station food, and we ate at Nui and Lagoon Grill at Waikoloa Village. 

While returning from Waipio Valley Lookout, we stopped in Waimea, Hawaii, and ate brunch at Hawaiian Style Cafe. We highly recommend the french toast! 

Final thought:  Hawaii has always seemed like it would never be within my family’s financial reach. For six of us to go for ten days and have two hotel rooms, the trip came in at a $30,000 point redemption. That is almost half of my teacher’s salary for a year! 

Points and miles can be life-changing if you use credit cards responsibly and stick to your financial goals! 

PS: This blog post could have easily turned into a novel. Message me on IG @pointsandmilesteachers if you have questions, and I’ll do my best to answer. 

Credit cards that made this trip possible

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