Island Hopping in Hawaii on Points and Miles


We have often flown and stayed in Hawaii on points and miles, but we usually stay on just one island. For this family trip, Alex wanted to try out two islands and two Hyatts to compare them. I figured that if she was up for doing this with four crazy boys ages 2-11, I could meet the challenge also! Here is our report on island hopping in Hawaii on points and miles. If you’d like to hear our PODCAST that talks even more about this trip, listen here!


Family of 6 standing in front of hotel



Alex gets the win in this department with her Southwest Companion Pass, which pays for one family member to fly for free + $11.20 in taxes and fees. Her husband also has a Companion Pass, so two of their kids flew free. She only had to use points for 4 tickets instead of 6! When she initially booked the flights, they cost more in points than she ended up paying for them. Once Southwest posted a sale, she rebooked her flights and received the miles back into her account. All in all, she paid 120K points and $84.00 to fly from SLC—LIH (Lihue, Kauai) with a stopover in Oakland. This includes her return trip from Maui and the inter-island flights. When traveling with her family, she likes a connection to refuel the troops and give them a chance to walk around.


southwest flight with kids

Alex says her kids don’t think there is another airline other than Southwest!


I found cheap cash prices on United from Denver to Lihue, so we went that route, using our United TravelBank credits from our American Express Platinum Card (that is how I use my airline incidental credits). Remember, I don’t like to use my points on cheap seats, although it is perfectly fine for others to do that.


First Stop—Kauai

Alex’s first trip on points and miles was to the Grand Hyatt Kauai, and she’s always wanted to go back. We have a timeshare we bought (before we knew about using credit card points and miles) in Princeville. It is definitely the rainy side (and incredibly beautiful because of that). When we were at our timeshare, we would head to Poipu whenever it was rainy, so it was an area we enjoyed.

We grabbed our rental cars. One of our favorite travel tricks is sending one person to the rental center while the other grabs any checked bags. This gets us on our way sooner. From Lihue airport, it is about a 30-minute drive to the Grand Hyatt.


Hotel with palm trees

The lush vegetation around the Grand Hyatt Kauai is one of its best features.


Grand Hyatt

When we arrived at the Grand Hyatt, we were warmly greeted and told that we had been upgraded to a Premium room because we had Globalist status. The lobby is gorgeous, as are the grounds and pool area. It is a HUGE property, and we were regularly getting in 10,000+ steps a day! We booked it for 25K Hyatt points/night, although the price has now increased to 30K points/night on average.

Our room was very large, with a king bed, a queen bed, and a pull-out chair that made a bed for one person. Alex had an identical room. We found my favorite Macadamia Nut Caramel Corn in the room, Hawaiian cookies, and chocolate macadamia nuts.  The room was nice but didn’t wow me, although I hear they are renovating the rooms, so I think that will be nice.

Because we have Globalist status, we had access to the Club Lounge, which is where breakfast is served, snacks during the day, appetizers at night (light dinner), and dessert in the evening. For a family, this is a HUGE savings on the expensive food bill! Although the Grand Hyatt is a luxury property, this food is probably average. Nothing bad, nothing wonderful (except some yummy oatmeal craisin cookies I found one day)!


Hotel room with two queen beds of white

The Grand Hyatt upgraded room we had on our stay.

Pool Area

The hotel is situated on a beach, but it is pretty rough with a lot of rocks. You can see surfers using it but not too many other people. However, the pool area is MASSIVE—we NEVER had to look for a seat, and we were there during Spring Break.


Lagoon area of hotel


There are several pools, slides, a sandy lagoon area (our favorite area), and numerous lawn games near the pool area. The grounds are lush, full of flowers, and just beautiful. That is part of the luxury that is the Grand Hyatt and makes it what it is.


Little boy drinking with straw near lagoon area, nachos in foreground

This little boy absolutely loved the sandy lagoon area.


We actually never ate at the restaurants, but Jess says in her review that they are excellent. We did order food poolside, and it was very good. On this trip, we tended to have late lunches and just weren’t hungry enough to eat a big dinner, so utilized the Club lounge instead.


We were there on Easter, and the resort had a lot of fun activities for children—water gun wars, Easter egg hunts, decorating sugar cookies, etc.

We went to Hanalei one day and had a fun beach day there, stopping off at Tropical Taco for late lunch. The little beach town of Hanalei is just so cute! The waves weren’t great that day, but we have often rented surfboards or boogie boards to use there.


boys with mom on beach

These two boys had so much fun on the beach in Hanalei.


three boys near waterfall and pool area

These three boys had a grand time at the Grand Hyatt Kauai!


Poipu Beach is very close to the Grand Hyatt and a great place to snorkel or hang out at the beach. It also has a park there and is a great place to take children. When we were there, there was a huge seal sleeping on the sand, and every night, numerous big turtles would come up to delight a captive audience.


Flight to Maui

After four nights on Kauai, we took a quick 30-minute flight on Southwest to Maui and continued our island hopping to Hawaii on points and miles.  Alex used 3.5K Southwest Rapid Rewards to book these flights (and her companion pass). Again, a very cheap and quick flight. It takes a bit longer to get to the Hyatt Regency located on Kaanapali Beach.

There have been many times the traffic to that area of Maui is slow and it can take an hour to drive there, so we were pleasantly surprised it was only about 35-40 minutes. It turns out that most of the inter-island flights take place after the flights from the mainland—great idea!


Family of 8 standing near palm trees and ocean

Hyatt Regency Maui

A few years ago, we went to the Hyatt Residence Club Maui, which is next to the Hyatt Regency Maui. The Residence Club is harder to find availability now, so we booked the Hyatt Regency for 25K points/night. It recently moved to a category 7 hotel and now is bookable at 30K points/night.


Hotel room with sofa bed and view of ocean.

I didn’t get a suite upgrade like Alex, but I was not mad about this room a bit!


We were upgraded to premium rooms. In fact, Alex got an upgrade to a suite. We were there to celebrate her eldest son’s birthday, and they went above and beyond. Housekeeping had written Happy Birthday in flower petals and had a cake of towels on the counter. They had a basket of yummy treats, a birthday cake in the fridge, along with some drinks. Another trick—if you are celebrating an important occasion, always let the hotel know. You could receive an upgrade, treats, or some other celebratory item.

Although we didn’t have a suite, it was a huge room, and they have been renovated so that the style is more in keeping with my aesthetic. Simple and spa-like. Alex and I both noticed that we were more drawn to the rooms at the Hyatt Regency than the rooms at the Grand Hyatt.

Pool Area

There are two pool areas at the hotel, one is primarily for children, and it has a small slide for little ones and a larger slide that we all enjoyed. We parked ourselves in front of this area every day. There is a main pool area, too, with a swim-up bar and waterfall area. Unfortunately, it is much more difficult to find a seat at this hotel as it is not as big as the pool area at the Grand Hyatt Kauai.


Children's splash area near hotel

This is the children’s area of the Hyatt Regency Maui.

The grounds are still gorgeous, though, and there are penguins, birds, flamingoes, and fish to see on the grounds. You definitely won’t get your steps in just walking around the hotel grounds, but right in front of the beach is a nice sidewalk, and you can walk past many other hotels and condos. We enjoy walking to Whaler’s Village for shopping or eating.


Woman and child standing near Aloha sign

Being able to go on family trips to create memories is this grandma’s dream.



We ate at the restaurant near the pool areas, and they had delicious fish tacos. The Club Lounge had the same offerings every day as the Grand Hyatt did, but they were more kid-friendly. One night was macaroni and cheese, and another night was hamburgers. We all agreed that they did the food in the lounge a little better, and there was more seating there, too.



This hotel is located right on Kaanapali Beach, and my grandchildren loved snorkeling, boogie boarding, and building sand castles right in front of our hotel. We always enjoy going to DT Fleming Beach for boogie boarding or Black Rock Beach (located in front of the Sheraton).


Sand, Ocean, and people in water.


In front of the Residence Club is a huge grassy area, and it is perfect for playing soccer, a game of catch, or for the children just to run around. You can use the facilities at the Residence Club when you stay at the Hyatt Regency, and we found the lounge chairs around that pool to be much easier to grab.


Which is Better?

Island Hopping in Hawaii on points and miles to two locations means everyone wants to know which is better. It’s kind of like asking which child you like most. Each has its merits, and one comes out on top in one area, and one comes out on top in another area. Both are luxury vacations on gorgeous islands, and everyone is going to have a different opinion.

  • Quiet Island Experience—Grand Hyatt
  • Night Life with Tons to Do—Hyatt Regency
  • Updated Rooms—Hyatt Regency
  • Large Pool Area—Grand Hyatt
  • Proximity to Beach—Hyatt Regency
  • Club Lounge—Hyatt Regency
  • A WOW Outdoor Experience—Grand Hyatt


Bottom Line

Island hopping in Hawaii on points and miles was a complete success. Grandchildren, parents, and grandparents all had a great time. I would say the only thing I would do differently is to spend 5 nights in each place. It just wasn’t enough.


Related Posts

Podcast #5: How You Can Visit Hawaii for Nearly Free

A Grand Stay at the Grand Hyatt Kauai

How to Visit Kauai on Points

Reader Success Stroy to Maui

Palm trees, sand, and water at sunset

Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a Travel Mom Squad advertiser, but we always show the best public offer even when we don’t earn a commission. Terms Apply. 

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  1. Jessica says:

    Hello-thank you for sharing your journey. My family and I are traveling to Grand Hyatt Kauai in December 2024 to January 2025. It will be my family’s first time in Hawaii and we are very excited. I appreciate the review! 🙂

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