How We Travel Hacked Hawaii for 4
We've been low-key travel hacking for a couple of years, now - mainly in a very passive way, collecting the points, booking one-off hotel stays with points and using points to pay for domestic flights. But, in early-2023, we each earned companion passes on Southwest, which allowed us all four to fly for the price of two on Southwest flights through the end of 2024. So, we wanted to make the most of this incredible advantage while we could.
The thing with travel hacking is that you kind of have to be aggressive about it if you want to get the best deals - long-haul flights in Business class for a steal, luxury all-inclusive hotel stays on points, etc. And, we just don't plan far enough in advance to be so serious about it. It boggles me how far in advance some folks are able to plan (usually 1-2 years when travel hacking)!
So, when March rolled around last year, we started thinking about how we could use our points over the summer, knowing we'd be hard pressed to find many good deals so late in the game. Having already collected quite a few points after opening the Chase Sapphire, Chase Ink, Chase Freedom and Southwest Cards and getting their sign-up bonuses (SUB), we were on to working out how to best economize our points to get as much out of them as possible.
After some discussion about where we'd go, we knew that our whole family was ready to go back to Hawaii after our dreamy 2021 vacation there. This time, though we wanted to try another island, and set our sights on Maui. I'd been to Maui when my sister got married eons ago, but hadn't been back since. Gui and the kids had never been, so we looked into it and decided it was the perfect next stop for us. We had no idea just how lucky we were to have gone when we did until we started hearing about the devastating fires that destroyed so much rooted history there just two weeks after we left.
One of the most popular hotel chains for travel hackers is Hyatt because of how easily and economically Chase points can be used on their rooms. In Maui, there are quite a few Hyatts to choose from. It was March 31st and we were looking go anywhere in June, July or August. Normally, travel hackers will say that's way too late to be looking, but being flexible on dates, I think was a huge help for us. Flights from Maui to the Big Island are so easy and cheap, that we tacked on to the end of our trip a quick stop to the Big Island to see friends before departing back to the main land. Here's a breakdown of what we were able to book on March 31, 2023 and how many points it took for our family of 4 to fly to and stay in Maui and the Big Island for our 10-day stay:
Booked flight from Austin to Maui, via Las Vegas for 37,606 points each adult, 0 points for kids who flew as our companions thanks to the SW Companion Pass. Paid $5.60 security fee for each passenger.
Booked flight from Kona to Austin, via Las Vegas for 31,946 points each adult, 0 points for kids who flew as our companions. Paid $5.60 security fee for each passenger.
Booked one room for 4 at Hyatt Regency Maui for July 8th-13th paying 140,000 points for the entire stay. No fees.
Booked flight from Maui to Kona for 2,163 points each adult, 0 points for kids who flew as our companions. Paid $5.60 security fee for each passenger.
Booked one room for 4 at Marriott Kamehameha Hotel in Kona for 3 nights paying 84,000 points for the entire stay. No fees.
Booked car rental for 3 days in Kona with Hertz paying $125
Points used for flights (Southwest): 143,430
Points transferred for hotels (Chase): 224,000
Cash spent for travel and stay: $169.80
The beauty of the Hyatt hotel we booked is that it has everything you need all in one place: several restaurants, a local coffee shop, the beach, multiple pools, a mini water park, pool bar, cultural workshops for kids and adults, beach chairs, gyms and a small game/lounge area. We would have been happy never leaving the place, and in fact it was a brutal goodbye when check-out rolled around.
In contrast, there is very limited choice of hotels on the Big Island, especially as late as we looked. We ended up at the Marriott out of convenience really, and I wouldn't recommend staying there. They had a pool, some shops, a small game room and Kona Ice in the building, but it was a huge letdown in terms of room amenities and comfort, especially after having been so spoiled in Maui.
I can't say enough about how impactful this trip was for us as a family and as our first successful travel hacked vacation. It's easy to see why people fall in love with these islands and the loving spirit of their people. We know that any future trips we make will need to have some cultural education and awareness element to them. I'm so grateful we were able to visit and support the local businesses in Lahaina while we were there. We're hoping to return one day and contribute what we can to their local economy. There's, apparently, still so much left to rebuild, and locals continue to pick up the pieces. If you're so inclined, consider donating to the Maui food bank to support those most severely affected.
How We Travel Hack
In 2023, we travel-hacked some pretty amazing trips, including a solo trip to Rome, a family vacation in Maui and we booked our first trip of 2024. This was the first year we really tried to take advantage of our points, and we're realizing that we've just barely scratched the surface with travel hacking. We first learned about travel hacking through the ChooseFI folks several years ago. With family all over the place, there is almost always a reason for us to plan a new trip - especially during those excruciating hot Texas summers.
Rome for One
Aging is wild. It's incredible to think of all of the versions of myself that exist in the past. Young-and-totally-confused Sarah. Young-and-totally-fearless Sarah. Move-across-the-world-alone-and-live-with-a-complete-stranger Sarah. Convertible-Corvette-driving Sarah. Expat Sarah. Working professional Sarah. Francophone Sarah. Young mom Sarah. And, recently, I feel like I'd reached the version of myself that could either be old mom Sarah or scared-of-everything Sarah. This version of myself that doesn't quite understand how to be alone for long periods of time without kids and schedules and routines and a healthy dose of chaos.
New York, again
About a month ago, I booked us all on a flight to New York for the first week of the new year. Gui and I had been thinking about taking a quick trip somewhere to break up the monotony of the 3+ week winter school break. We never really settled on going anywhere because the thought of all the planning, reserving, renting, etc. that we'd need to do ahead of time kept us both in that talking phase and incapable of moving into the action phase. Planning for trips is so exhausting now. I remember when Gui and I would make a decision to go somewhere, book a flight and jump on a plane within a few weeks without so much of a misplaced hair to show for it. Although it's easier now than it was with younger kids, I will say that planning trips for 4 instead of 2 is not something I ever look forward to doing.
In-between times
Christmas 2023
This year, I made simple goals for meals and decided to keep my stress levels as low as possible by sticking to my tried and true comfort foods. I've also gotten better at setting reasonable expectations of my time when it comes to cooking. I remember getting so overwhelmed after choosing lofty menus and complicated recipes in years past, but I've finally decided not to over-complicate things so I only feel enjoyment from the time spent in the kitchen. It doesn't make sense to feel reluctant about spending so much time cooking if I don't want to be doing it. Last year, I made the decision to order a premade duck confit Christmas dinner, and it was all the rage with everyone. This year, I knew I'd have a lot of time at home, and opted to keep it more homemade.
So, we did our usual smoked salmon, cheese and charcuterie board for Christmas Eve. We added a chocolate panettone to the mix this year for dessert because we couldn't get enough of one at a friend's house earlier in the week. For Christmas linner, I stuck to a long and slow braised beef short rib with grandpère's gratin and grilled red cabbage with mustard sauce. Avienne's gotten more curious (and helpful!) in the kitchen, so she helped me whip up a very rustic bûche de noël that managed to be tasty despite my missing a few ingredients.
It was an indulgent couple of days, and we were all reminded how grateful we are for the food and gifts we all luxuriated in this Christmas.
NYC...a month later
These days chez nous
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