The Pafford family 2026 Spring Break trip was a direct result of my playing the credit card points and miles game. I just fished around and found flights for four to Hawaii and back from DFW. This cost me just the sign up bonus for a single credit card. I signed up for the American Express Delta Business Gold card. I spent about $5,000 on it that I was already going to spend anyway. I received 90,000 Delta miles as a sign up bonus, and earned about another 10,000 from spending the $5,000. By being a bit flexible on our travel dates, I was able to find an “open jaw” flight for all four of us for 97,000 Delta miles and $44.
An open jaw itinerary flies to one destination, then returns from another. We could have flown round trip to Honolulu and back for about the same price, or maybe a bit less. That would have been less interesting. We would fly to Honolulu the Wednesday before the start of Spring Break, and return the Tuesday afterward from Maui. I found a puddle jumper flight from Oahu to Molokai, and we would take a ferry or water taxi to Maui from Molokai – a distance of only about seven miles.

We took further advantage of the points and miles game by booking the Hyatt Regency Maui Resort and Spa with points transferred from Chase travel cards. Stephanie received a credit from AirBnB for her good management of our short term rental in Spur, and this covered part of our stay in Molokai. The motel in Waikiki was paid for with points as well. Although Hawaii is an expensive destination all the way around, this was a trip we would not have made if we had not been able to cover the most expensive aspects – flights and motels – almost completely with credit card redemptions.

Playing the points and miles game requires some degree of flexibility, but that requirement is often quite small. To get a great deal, you cannot insist on precise dates and locations. In our case, to make the trip work we simply had to travel on some days other than the Friday or Saturday Spring Break began and the Sunday it ended. By allowing the kids to miss a day or two of school on either end, we saved 75-90% over flying on the peak dates. Staying in an AirBnB on Molokai (a less popular island) for the nights in the heart of the break also helped keep costs reasonable.

We still had to foot the bill for rental cars, admissions, and food. We mitigated some of the food costs by eating out not more than once per day. We also used public transportation where possible. Although Oahu’s buses and Sky Train were not free like the HeleOn buses on the Big Island, they were a lot cheaper than renting, and I wasn’t constantly shelling out for exorbitant parking fees. In many cases, admissions cannot be avoided. Even combining the Pearl Harbor museums into a collective “passport” bundle, we paid $350 to see those exhibits. The Bishop Museum and Iolani Palace were closed due to inclement weather (see the Oahu page), but had they been open, they also would have been expensive. The Waikiki Aquarium was more reasonable. We also saved some by golfing on less popular Molokai, rather than the fancier clubs on Oahu and Maui. The Oahu golf courses were not playable the days we were there anyway.

Rental cars on Molokai – and many other things for that matter – are arranged in a kind of ad hoc manner. You can pay individuals to rent cars that are parked near the airport. Tours can be paid for in cash, or via avenues like Venmo or PayPal. The more commercialized islands of Maui and Oahu utilize more professional reservation services. We arranged our lei making tour and our water taxi in person, for cash. We paid cash for our car and bike rentals on Molokai as well. We reserved cars and attraction entries online for things we did in Maui and Oahu.

Storms and their aftermath impeded a lot of what we were able to see and do on this trip, but we saw some highlights, and experienced the parts we could. While I would always prefer to maximize what I see and do in a new place, it does deaden the pain a bit knowing that such a trip would likely have cost around $10,000 had we paid for all of it in cash. We ended up spending less than a quarter of that amount – a remarkable accomplishment for a trip to a place like Hawaii, if I do say so myself. I read of and met a few people who either flailed to try to cancel their trips at the last moment, or lamented their bad luck at not being able to do everything they would have liked in Hawaii due to the weather. Had we spent five figures on the trip, we may have felt this trip was a “once in a lifetime” experience, and thus felt a lot worse about not being able to completely optimize our sightseeing. Since we were able to work most of the trip free based on credit card points and miles, we know we will have other trips to other places, and we’ll be able to come back here again another time when the weather is better, if we so choose.