How I Booked a Family Vacation to Hawaii Using (Mostly) Points & Miles

Hawaii has always been on my family’s bucket list. So after not traveling for almost 2 years, my wife and I decided to take our 2 kids to Maui and Oahu.

We (as most travelers have) quickly realized that traveling post-pandemic is pretty intense. Flights are full, hotels are busy, and prices are expensive! We had a few weeks to work with around the holidays and school schedules in January 2022, so I got to work trying to make the most of our points and miles.

Unfortunately, I am not writing the ultimate redemption success story, mostly because we didn’t get our preferred flights, there were cancellations, and we still spent a fair amount of cash. However, I am still quite happy with the trip and can easily say it would not have been possible without points and miles.

This is more along the lines of what you could expect if you were to book a trip to Hawaii right now — not perfect, not as “free” as people brag about on social media, but with the right mindset, some good people, and a few points, it is possible to book yourself a great vacation.

All said and done, this was easily a $15,000+ trip. However, I only spent $2,000 out of pocket and covered the rest with points and miles that my wife and I had been accumulating. We aren’t big spenders and don’t constantly chase credit card welcome offer bonuses, but we are conscious about earning points organically and take advantage of promotions and category bonuses. This pretty much means any family can easily replicate this trip and probably do it for cheaper than we did.

Without further ado, let’s take a look at how I flew my family of 4 from the East Coast to Hawaii and back, staying in luxury hotels and saving money along the way — and how you can do it, too!

Flights

My wife, kids, and I had spent the holidays in New England with family, so I (originally) booked us a flight out of Boston Logan International Airport (BOS) to Kahului Airport (OGG).

I had been sitting on a stash of Virgin Atlantic Flying Club Points from a canceled ANA flight to Tokyo, so I was really looking forward to using them to fly to Hawaii. My goal was to use them to fly on Hawaiian Airlines direct from Boston to Honolulu (HNL) in first class, which is the longest nonstop flight in the U.S. However, as we have all seen, partner award availability is hard to come by lately.

After months of searching, I finally gave up and settled on using the miles to book Delta BOS-SEA-OGG for 30k miles each in economy. Not nonstop, not first class, but I couldn’t complain about the price.

However, all of that searching and planning turned out to be a waste of time, because the night before our flight, a huge snowstorm descended on Boston and all flights for the following day were canceled!

We were automatically rebooked on flights 2 days later, but that meant 2 fewer days in Hawaii and it would complicate our existing reservations. So, instead of just waiting around in the snow, I got to work and found the last flight out of Boston before the storm hit.

I couldn’t find anything reasonably priced to Hawaii, but I knew we needed to get west. I was shocked (and thrilled) when I found 4 business class seats to Los Angeles International Airport (LAX) leaving in 3 hours.

I put the flights on hold, my wife packed up everything she could, and I went to pick up the kids who were out with their grandmother. Sorry, Nana!

American Airlines BOS-LAX

Despite crazy last-minute cash fares, American Airlines still had 4 business class seats on a direct flight to LAX for only 22,500 each — on one of my favorite planes, no less!

Obviously spending 90,000 AAdvantage miles was not planned, but fortunately, I had them available. Plus, after a quick text with Virgin Atlantic, the 120,000 points from the rescheduled flight were back in my account.

Cash prices were over $700 (and not much cheaper for economy), so I got over 3 cents per mile, which is more than double the Upgraded Points miles valuation.

This flight was on a 3-cabin Airbus A321, so business class wasn’t even the best seat. However, when flying as a family of 4, the 2-2 business class setup is preferred.

The last-minute change of plans was a blessing in disguise. After the chaos of rebooking, packing, and rushing to the airport, we got to relax in the lounge and have a bit of a breather with the kids before boarding.

The flight was extremely comfortable, and I know we all preferred sleeping in a lie-flat seat as opposed to the original flight to Seattle in economy.

And despite the need to get a hotel at the airport that night (more on that below), taking this flight and breaking up our journey made the long-distance journey to Hawaii not feel not so bad. I am positive it helped with our jetlag when we finally made it to Maui.

Oh, that’s right, we still need to get to Maui!

Total Cost: 90,000 American Airlines AAdvantage miles + $22.40 in taxes and fees

Estimated Value: Seats were $700+ each, so we got over $3,000 in value

How I Earned Those Miles: I earned most of those miles from the recent SimplyMiles promotion

American Airlines LAX-OGG

I didn’t have much time to figure out our flight to Maui … pretty much just the few minutes spent in the Admirals Club in Boston.

After running through all of my normal searches, I couldn’t find anything worth spending miles on. Either the flights were too expensive or would get us into Maui too late. So, against all odds, I paid cash.

For $149.50 each, we flew American Airlines from LAX to OGG in economy. I thought that was a fair price for a last-minute flight to keep our bucket list trip on track.

Plus, we ended up getting to Maui 2 hours earlier than our original flight, and we had less jetlag thanks to the overnight stay in Los Angeles.

The 5.5-hour flight was operated by an Airbus A321neo, so not as nice as the A321 we flew the night before. There was no IFE, but we were prepared with iPads for the kids and they did really well since they were well fed and had a good sleep.

The economy section was a 3-3 layout, so we chose window and aisle seats, one row in front and the other behind, and we were lucky enough to have the middle seats stay open. Had someone booked the middle seat, we would have simply offered to swap.

Total Cost: $598.00 — I used my Citi^® / AAdvantage^® Platinum Select^® World Elite™ Mastercard^® as I was working on a 7,500-mile retention offer, earned 2x miles on the AA flights, and received free checked bags and preferred boarding

Hawaiian Airlines OGG-HNL

After a week on Maui, we headed to the island of Oahu and flew into Daniel K. Inouye International Airport (HNL).

Intraisland flights are generally pretty cheap, so I booked us economy seats for $49 each from OGG to HNL.

However, when we decided to extend our stay on Maui to check out a hotel that just released some award availability, I had to rebook and prices had jumped a bit. I ended up having to pay $79 each, but there were no change fees, so it was worth it.

The 35-minute flight was on a Boeing 717, which was perfectly comfortable for the quick flight. The economy section was a 2-3 layout, so my wife sat with the 2 kids and I sat across the aisle.

Total Cost: $316.14 — I used my Citi Prestige^® Card which earns 5x on travel and triggered the $250 annual travel credit

Delta Air Lines HNL-LAX-ATL

We needed to get to Hartsfield-Jackson Atlanta International Airport (ATL) to catch our flight back to Rio de Janeiro (GIG), so flying Delta was an obvious choice.

A direct HNL-ATL flight exists, but it wasn’t available with the Virgin Points that I wanted to use from our canceled flight.

After plenty of searching, I paid 27,500 miles each for a red-eye flight with a connection at LAX. It was far from ideal, but the price was right.

The daytime flight from Honolulu to Los Angeles was fine, but a bit bittersweet as our vacation was coming to an end. After grabbing a quick dinner at LAX, we boarded a very full flight to Atlanta on the very smooth and comfortable A350-900. Again, we got lucky with the middle seats staying open on the red-eye flight so the kids were able to spread out a bit.

Total Cost: 110,000 Virgin Atlantic Flying Club points + $22.40 in taxes and fees

Estimated Value: Seats were over $300 each, so we got about $1,200 in value

How I Earned Those Points: I had a lot of Virgin Points redeposited into my account after our flights to Japan on ANA were canceled in 2020 due to the pandemic; most of those points were transferred from American Express with a 30% bonus

Bottom Line: All said and done, I spent 200,000 miles + $958.80 for 4 round-trip flights from the east coast to Maui and Oahu. No, that is not the greatest redemption story (far from it), but it did allow my family to fly in business class on the most important flight and gave us the flights we needed when faced with last-minute changes. But all things considered, 50k miles + $240 per person for all of those flights is not terrible. Learn about the best ways to fly to Hawaii with points and miles in our detailed guide.

Hotels

For what was lacking in solid points redemptions with flights, I made up for with hotel stays.

We had a total of 13 hotel nights — all paid with points — at nice hotels.

Hyatt Regency Los Angeles International Airport

Our 8-hour stay at the Hyatt Regency Los Angeles International Airport was unplanned but enjoyable.

While on our flight from Boston, I booked us a room at the airport hotel so that we could easily get back to the terminal the following morning for our flight to Maui.

The hotel is a Category 3 property, so I used a Free Night Award from The World of Hyatt Credit Card. Rates were around $250, so that easily justified the $95 annual fee.

The hotel provided a shuttle that picked us up and dropped us off at our terminal. And since I have Globalist elite status, all 4 of us got free breakfast, which was honestly a really impressive spread for an airport hotel. We ate very well before our flight!

Total Cost: 1 World of Hyatt Free Night Award

Estimated Value: Subtracting the $95 annual fee from the $250 rate, I got about $155 in value from that award

How I Earned Those Points: Each year upon renewal of my World of Hyatt card, I get 1 Free Night Award that can be used at any Category 1 to 4 hotel

Hyatt Regency Maui Resort and Spa

Besides actually visiting and exploring Maui, one of the things that we (especially my kids) were most looking forward to was our stay at the Hyatt Regency Maui Resort and Spa.

I had been building up my World of Hyatt points balance over the past 2 years and now had Globalist status, so redeeming the points at this gorgeous Hawaiian property was a great call.

The beachfront resort is absolutely stunning with multiple pools and great activities for kids, and it had tons of perks for elite members.

I was able to book 5 nights at 25k World of Hyatt points per night. That was more challenging than I thought it would be, as the hotel (and Hawaii in general) has been really busy, and standard awards weren’t readily available.

As a Globalist staying on an award reservation, I received a complimentary upgrade to an oceanview room, waived resort fees, free parking, Regency Club access, and more. The Regency Club access meant that my family of 4 received free breakfast, snacks, and a light dinner for free every day. That saved us hundreds of dollars over the course of our stay!

Besides being our favorite hotel of the trip, it ended up being the cheapest, as well! We can’t wait to go back.

Total Cost: 125,000 World of Hyatt points + $0 in resort fees and parking

Estimate Valued: Rates were around $800 per night, so I got over $4,000 in value (not including Globalist perks)

How I Earned Those Points: My wife and I both have The World of Hyatt Credit Card and have been earning and hoarding points with a redemption like this in mind

Hot Tip: In March 2023, Hyatt Regency Maui Resort and Spa moved up to a Category 7 and now requires 25,000 to 35,000 points per night.

Grand Wailea, A Waldorf Astoria Resort

Anyone interested in points and miles and Hawaii probably has the Grand Wailea, A Waldorf Astoria Resort on their to-do list — I was no exception.

I kept checking, but couldn’t find any standard rooms available for 95,000 Hilton Honors points per night (that rate has since increased to 110,000 per night) during our stay in Maui. However, after I booked our flights to Honolulu, 2 nights became available! So I rebooked our flights and booked 2 nights at the famous Grand Wailea.

The sprawling property is set on the stunning Wailea Beach on a quiet part of the island. The resort itself has a lot to offer, but unfortunately was going through an extensive renovation during our stay.

As a Hilton Diamond member, I received an upgrade to an oceanview room, a $50 daily food and beverage credit, and waived resort fees (since this was an award stay). The $65 valet charge is not waived for elite members.

My kids loved this resort as it had a great pool with a bunch of waterslides, a lazy river, and a Baby Beach. But coming from the Hyatt Regency, I was a little disappointed with all of the extra charges, lack of decent elite benefits (such as a lounge), and intrusive construction noise.

I would like to go back once the renovations are complete and will likely try to use a Free Night Reward to help offset the standard room price increase on point redemptions.

Total Cost: 190,000 Hilton Honors points + $130 in parking fees

Estimated Value: Rates were around $1,100 per night, so I got over $2,200 in value

How I Earned Those Points: Most of those points came from Hilton Honors cards

Sheraton Waikiki

A first-time trip to Hawaii wouldn’t be complete without visiting the famous Waikiki Beach in Honolulu. Since our return flight was out of HNL, we planned to spend our final days on the island of Oahu.

After much back and forth, I finally decided to book 5 nights at the Sheraton Waikiki. Rates started at 60,000 Marriott Bonvoy points per night, but I wanted to guarantee an oceanfront room, so I booked an upgraded room for 70,000 points per night. When booking Marriott Bonvoy award nights, the fifth night is free when you reserve 4 nights, so the total came out to 280,000 points for 5 nights.

But it took a while to land on the Sheraton Waikiki. Honolulu is a big city, so there are a lot of hotel options, which made research quite time-consuming. After I settled on using Marriott Bonvoy points, I narrowed our options down to the Sheraton Waikiki and The Ritz-Carlton Residences, Waikiki Beach. It seems crazy to think that I chose a Sheraton over a Ritz-Carlton, but I think I made the right decision.

I had actually reserved The Ritz-Carlton but ended up canceling after closely comparing the 2 properties. The Ritz-Carlton Residences is gorgeous and newer, with apartment-style rooms, but it’s not beachfront. That meant walking a couple of blocks to the beach with kids in tow. Plus, there is no really good option for the kids to use a pool. Just a nice infinity pool, which is awesome for adults.

The Sheraton, on the other hand, had 2 pools, one of which was the Helumoa Playground pool full of water slides and play areas. It was also just steps from the sand of Waikiki Beach, so we could bounce back and forth between the beach and pools all day without lugging our gear with us.

The Sheraton Waikiki had plenty of affordable dining options, plus it is located right on the main strip in Waikiki, so we were surrounded by great shops and restaurants. For our family, it was a great fit.

Total Cost: 280,000 Marriott Bonvoy points + $210 in resort fees

Estimated Value: Rates were around $300, so I got over $1,500 in value

How I Earned Those Points: Most of the points came from my wife’s Marriott Bonvoy Brilliant^® American Express^® Card welcome offer and hotel spend.

Bottom Line: All said and done, I spent 595,000 points, 1 Free Night Award, and $340 in fees for 13 nights at really nice Hawaiian hotels. All of those points have different valuations, but it gives a nice overview. An average of 46k points + $26 per night is an absolute steal in my book when visiting Hawaii during the peak travel season. You can also consider our guide to the best Hawaii hotels to book with points for max value.

Rental Cars

Personally, I love having a rental car when traveling, especially to a new destination. Being able to explore at my own (and my family’s) pace is a great way to wander off the beaten path and find unique experiences.

So when we booked our trip to Hawaii, I knew I was going to cruise around the islands.

The only issue was the INSANE rental car prices. We are all seeing what happens when companies sell their fleets and then travel demand comes roaring back. Less supply + more demand = higher prices!

Hertz on Maui

Having a rental car in Maui was non-negotiable for me.

Yes, some people will get a ride to the resort and stay put for a week, but not me and my family! Besides moving hotels, we also planned other activities around the island including driving the Road to Hana. Plus, parking was free at the Hyatt Regency with Globalist status.

However, a week-long SUV rental from Hertz at the Maui airport in January 2022 was over $2,000! It was honestly unbelievable. Fortunately, as the trip got closer the prices dropped and I was even able to redeem my Hertz Gold Plus Rewards points for the week-long rental.

I have President’s Circle status with Hertz, so that means I can choose (almost) any car in the lot. So after we arrived on Maui, I took the cute airport tram to the rental car garage and grabbed a brand new Chevy Blazer.

This was a great option for us, as (most importantly) it fit all of our luggage, was good on gas, and was comfortable on the long drive around the island.

Maui is such a beautiful island, so being able to explore it at our own pace was great.

Total Cost: 3,750 Hertz Gold Plus Rewards points + $145 in taxes

Estimated Value: Rates dropped to around $1,000 for the week, so I ended up getting about $850 in value (not including the upgrade)

How I Earned Those Points: I earned those points from renting cars over the years; I only redeem them for week-long rentals, as that is the best value

Turo on Oahu

During our time on Oahu, we didn’t need a car as much. Being right on Waikiki Beach puts you in the middle of all the action in Honolulu — plus the parking is expensive.

However, we did want to explore the North Shore and other parts of the island, so I looked into renting a car for 2 days.

The major car rental companies were still charging a fortune, close to $200 per day for a basic car. Instead, I turned to Turo where I was able to rent a Tesla Model 3 for less.

The Tesla I chose was $99 per day, but after all of the extra fees and insurance, it came out to $183 per day. Part of those fees were add-ons that I chose, including daily pick-up and drop-off and charging. Had I not added those options, I would have had to pay for parking and charging at the hotel, which would have cost me even more. So, it was still a better deal than a traditional rental, plus it was much more convenient.

The island of Oahu is so much more than just the Waikiki neighborhood, and cruising in the Tesla was a fun way to explore it. We visited the incredible Lanikai Beach, the Banzai Pipeline on the North Shore, hiked Diamond Head, and more … things we simply wouldn’t have done without a car.

Total Cost: $366 including insurance, parking, delivery, and charging for 2 days

Hot Tip: I booked the Turo rental using my American Express Blue Sky^® Card as it had a targeted Amex Offer to spend $150 and get $30 back. For Turo rentals, you could also consider using a card that earns bonus points or cash-back on transit, such as the 3% cash-back on the Blue Cash Preferred^® Card from American Express. 

Total Cost

This was not an inexpensive trip.

Even though most expenses were covered by points and miles, it was a lot of points and miles. But, at the end of the day, that’s what they are there for! To be enjoyed, right?!

In total, for 13 hotel nights, 4 flights, and 2 rental cars, my family of 4 spent:

• 200,000 airline miles
• 595,000 hotel points
• 3,750 rental car points
• $1,904.80 on flights, cars, taxes, and resort fees

Of course, there were some additional expenses like meals and souvenirs, but nothing out of the ordinary.

Final Thoughts

Looking at the final numbers can be a little startling. But this was a bucket list trip and we had been sitting on those points and miles for years after multiple canceled trips due to the pandemic.

Spending 2 weeks in one of the most beautiful places on earth with my wife and 2 children, staying at luxury hotels for less than $2,000 out-of-pocket? That works for me.

We got $13,000 worth of value out of those points and miles, and they helped us make last-minute changes and fly business class to keep the trip on track. That’s an excellent redemption in my book, especially because it was a trip that my family loved and will always remember.

Have you done Hawaii using points and miles? Let me know your favorite redemptions in the comments so that I can start planning my next trip!

The information regarding the American Express Blue Sky^® Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.