Planning for Family Travel to Hawaii 101
Hawaii Trip – Part 1
Our most recent trip was to Hawaii. That’s where we were when we decided to start this site to help others. As I explained in our post “What’s This All About?“, the first several posts are going to be about this trip and will start with how to plan family travel to Hawaii. Future posts will continue the story about our actual time traveling to, from, and in the Big Island.
How Did We Decide to go to Hawaii?
In 2018, we went on a big trip to Europe lasting 2 weeks and visiting multiple sites. Then in 2019 we were welcoming our daughter Elizabeth in February. Because of this, we had decided not to go on a big trip this year and just do something domestically, nothing too big.
I know what you’re thinking, “Hawaii isn’t a small trip”. Though it is domestic, so we stayed with that part of the plan.
So how did we make that decision? Honestly, we were thinking about where to go late last year (around Thanksgiving 2018) and did a Google search on good trips for kids in the US. We found a couple of blog posts with titles like “Top 10 US Destinations for Kids” or something like that.
It turned out that we had already been to a lot of the locations listed. One place on all of lists that we hadn’t been was Hawaii. I did a little checking into how many points it would take and what we had and realized that we had enough to cover the flights and at least part of the hotels. At that point, we started to seriously consider it, and then made some firm plans in January of this year.
Which Island to Visit?
After we started looking into Hawaii, the first decision we had to make was which island would we visit. Since neither of us had ever been there before we had no reason to pick one island over another. The ones that are the most popular are O’ahu and Maui, then you have Kauai, Moloka’i, and the big island of Hawaii.
To make our decision, we needed to see which ones had hotels that we could use some points for, as well as which ones had flights available for rewords too.
First, I reviewed the hotels. We had a good amount of Marriott Bonvoy and Hilton Honors points. So, I started looking at what hotels in those programs were on each island and how many points they took to stay. One of the benefits of both programs is that they offer the 5th night free when you book using points.
The lowest category Marriott hotels in Hawaii are category 4 hotels on the Big Island and on Kauai. These properties take 25,000 points per night. So, with a 5th night free, that would be 100,000 points for 5 nights.
The lowest category Hilton hotels in Hawaii are category 5 hotels on the Big Island and O’ahu. These properties take 30,000 – 40,000 points per night. So with a 5th night free, that would be 120,000 – 160,000 points for 5 nights.
Note that as category 4 and 5 hotels, these are the cheapest points hotels for these programs in Hawaii but are mid-range when compared to many locations. Hawaii is not a cheap place to visit whether talking about the cost in dollars or points.
Looking at the locations of these properties, we could either stay on Kauai at a Marriott for about a week or stay on the Big Island at a mix of Marriott and Hilton for more nights. It turns out that on the Big Island, the Marriott hotel is in Kailua-Kona (West Side) and the Hilton is in Hilo (East Side).
These locations work out perfectly to split the stay between the two sides of the island. We had enough points at the time to book 7 nights (1 free) with Marriott and 2 nights with Hilton. This would put us in Hawaii for up to 9 nights depending on the flight options.
The hotels that fit this bill are:
- Kona – Courtyard by Marriott King Kamehameha’s Kona Beach Hotel
- Hilo – Grand Naniloa Hotel Hilo – a DoubleTree by Hilton
Personally, I think that staying longer in a place like Hawaii is a no brainer if you have the vacation days to spare. We did, so we chose the Big Island for our first trip to Hawaii!!
How to Get There?
Then we had to determine when there were flights that made sense going to the Big Island with reward seat availability for 3 seats (Elizabeth was a lap child, so no seat is needed).
With Vicky being a teacher, we had to plan for the trip to take place during the summer. Unfortunately, this is a popular time to visit Hawaii (and most places), since kids are out of school and families can travel more.
This also means that the seats airlines have set aside for rewards tickets get sold out quickly, especially if multiple seats are needed. Since the Big Island is not as touristy as O’ahu and Maui, it is not as visited. This means that while there are fewer flights going to Kona and Hilo, there is less demand for the reward seats, and they are available for longer.
In January there were still several options for flights with 3+ rewards seats. YAY!!
We live in El Paso, Texas, and for those of you familiar with it probably realize that the El Paso airport is not large and definitely not a major hub for flights. There are direct flights to some large cities in Texas, Phoenix, and California.
Alaskan Airlines recently started service from El Paso to Seattle and San Diego. This service started after we had made our plans, so I’m not sure about how useful this might be, but it will be worth looking at in the future.
In the search for what airlines made sense for rewards tickets from the mainland to Hawaii, it quickly became clear that flights from the West Coast to Hawaii booked through British Airways on American Airlines or Alaskan Airlines was the best choice. There is a popular “sweet spot” on British Airways for these routes.
British Airways rewards are based off distance of the flight segments. They are a part of the Oneworld alliance which includes American Airlines and has a separate partnership with Alaskan Airlines. Because of this, any of the west coast cities with flights on American or Alaskan to the Hawaiian Islands are in a sweet spot.
By booking these flights using British Airways Avios it costs 25,000 points roundtrip per ticket. American Airlines would charge 40,000-45,000 points for the same flight and Alaskan would cost you 40,000 points. At the time we were planning we had approximately 90,000 Chase Ultimate Rewards points. So, we had enough points for British Airways flights from the West Coast but not enough for some other options.
Using points in this way, the only cost is the taxes and fees, a total of $11.20 per round trip ticket for US domestic flights. This left us with a total cost of 75,000 points and $33.60 for the flights from LAX to Kona. (See below for more details on how to do this)
On May 30, 2019, British Airways changed their rewards chart, so that these flights will now cost 26,000 points roundtrip. Not a large change, but a devaluation
Of course, we would have to get to a West Coast city from El Paso to take advantage of these options. We have the most experience flying with Southwest. Looking at available flights, there are frequent options from El Paso to Los Angeles, with a few non-stop flights each day.
We didn’t have enough Southwest Rapid Rewards points for those flights. And if we used the Chase points for the flights from LAX to Hawaii then, we didn’t have enough points for the Southwest flights.
Fortunately, there are a few other parts of travel hacking along with just using points. Booking 3 non-stop roundtrip flights from El Paso to LAX cost $600. Let’s see how we were able to lower this out-of-pocket total.
Vicky and I each have the American Express Gold card. One of the benefits of this card is $100 per year of airlines credits. These credits are really meant to be used for incidentals and are not really supposed to work for airfare. There is a work-around for this that works with some airlines. You can buy gift cards for the airline to apply to the airfare. Since we each have one of these cards, we were able to get $200 worth of gift cards. This works by purchasing the gift cards with the Gold card. Then an equal credit shows up to offset the charge. That lowered the cost of the flights to $400.
Be aware that this is not a use for the credit that American Express approves, the credit is supposed to not be for airfare. There is some evidence that this has changed recently and will no longer work. I will update this as more evidence comes out.
Another credit we were able to use comes from the Chase Sapphire Reserve (CSR) card which Vicky has. The card comes with $300 per year of travel credit. This credit offsets $300 worth of any travel expenses per year. Since we made this purchase early in the year, we hadn’t used it yet and it was still available. This works by making the purchase with the CSR card, then a credit is applied for up to $300. This lowered the total cost of the flights to only $100.
How to Put it All Together?
At this point we had to try to find the right dates and time for all of this to work together. Since we were flying to LAX on Southwest and to Kona on American, we would have to exit the secured area, gather our bags, check in with American Airlines, and go back through security. We would need enough time to do all of this.
While it is possible to check in on-line or via mobile devices and thus skip the check in step, you still have to go to the counter when checking in with a lap baby.
Non-stop flights from El Paso to LAX on Southwest were available to leave at ~6:00 AM or ~7:00 PM. The flights from LAX to Kona or Hilo were available to leave at 8:30 AM on several days we were looking at and around noon on a few days.
The noon flights did not have availability on days that lines up with taking 9 days on the island, so we were going to have to go with an early flight. The benefit of taking the early flight is that we would arrive in Hawaii before noon and have the ability to enjoy our first day. (You Gotta love the time change 😊)
Trying to do all of the travel in one day would have us departing El Paso around 6:00 AM, landing in LAX at about 7:15, and then have to get our bags, change terminals, check in with American Airlines, and get back through security for a flight just over an hour later!! It might be possible to do this with no checked bags, and no little kids (still probably not).
There was no way we were going to even attempt this!!
The only other option was to fly into LA one day and out on the next. This would make it easier to plan the flights, but of course that would mean that we would need to stay in LA for the night. We decided to take the later flight out of El Paso putting us into LAX around 8:00 PM, with a flight the next morning at 8:30 AM. To make this work we needed a hotel close to the airport, preferably with a shuttle.
We have used a lot of IHG points in the past for stays and had about 70,000 points available along with a free night certificate due to having a Chase IHG Card. Looking at IHG hotels near LAX with a shuttle and reward space available, the Crowne Plaza LAX stood out as the best option at 35,000 points.
For the return flights from Kona to LAX, there were two daily departures. The earlier one at 1:00 PM which would put us in LA at 9:15 PM. Or a later one at 9:40 PM that would put us in LA at 6:00 AM the next morning. (You Gotta love the time change ☹)
There was no way we cold make any flights from LAX back to El Paso with those schedules. So, it looked like another night in LA was going to have to be factored in. Hello Crowne Plaza LAX again, I hope it’s a decent hotel for the night.
Now How Do You Actually Book All of This?
Flights
We will cover how to book the flight first since it is more complicated, and this is the order I would suggest to do it in. You want to review your hotels to ensure reward rooms are available for the dates you want to fly. But Make sure to lock in your flight reservations first, as the space is usually more limited, and hotels are usually a little more flexible.
After reviewing the dates that flights were available from El Paso to LAX and back (almost every day) and the dates that there were reward seats from LAX to Kona, we decided that our flights would look like this:
- June 22 – Fly from El Paso to LA
- June 23 – Fly from LA to Kona
- July 2 – Fly from Kona to LA
- July 3 – Fly from LA to El Paso
There was availability for both the Marriott and the Hilton Hotels we were intending to use for this entire duration, as well as availability at the Crowne Plaza LAX for the 2 nights in LA.
“How do I know there is availability on these dates?” you ask. Well, let’s take a look.
Note: Since we decided to start this blog while on this trip, I don’t have screen shots of all of the actual bookings I did. I will demonstrate with a hypothetical booking taking place In October 2019 to illustrate. In the future, I will strive to get actual shots of our bookings, so you can see how we do it.
We have already determined that we want to make an American Airlines booking through British Airways. So, we start by going to American Airlines.
I would suggest signing up for the rewards programs for any service you use. You never know when it can come in useful. Just make sure to keep track of all of your logins, especially if multiple people in your household have accounts. I use a simple excel spreadsheet with the program name, person, account #, password hint, e-mail associated with the account, and current Miles/Points. An example is attached for reference.
For these searches, I find it best to use the “Advanced/Multi-city search” option found on the main page. You do not need to be logged into your account to see the results.
I usually search for the flight segments as individual segments. Meaning a One-way flight from LAX to KOA and then a One-way flight from KOA to LAX. I just like to keep it as simple as I can, and this makes more sense to me.
On the search page make sure to select the box labeled “Redeem Miles” so that you will see the miles results not dollars.
Also make sure to select the number of passengers you need. You do not want to find availability and move points around only to discover there was only 1 seat at that price, not the 3 you needed.
For this search we are only interested in “MileSAAver” seats in the “Main Cabin” and only showing flights operated by “American Airlines”.
Once you have it ready, click “Search”. Once the results come up, you can choose to “Show Full Calendar”, and this will open a calendar showing 4 weeks of results. This is the main reason to use the AA search tool, it is much easier to see a variety of dates than the BA one. Make sure to set Number of Stops to “Non-stop only”. We are only interested in the Economy MileSAAver rates, so select that at the top as well.
Non-stops are required to make this redemption through BA work. BA books by flight segment, so we need to make sure there is only one segment.
The dates with available tickets will show in green. As you can see above, the rate is 20K for the flights, this is the one we are interested in. The rate is 20K during off-peak and 22.5K during peak season. For our example I will use a flight on October 20.
Once you select the 20th and click Continue, you will see the flight details for that day. Double check again that you are only seeing flights operated by American Airlines. Also, we need to make sure that there is a non-stop flight showing at the 20K price.
There is only one flight on this day that meets our search. Make note of the date, time, and flight number to confirm the details on the BA website later. October 20th, 8:36 AM, Flight 59.
Now, we want to do the same thing to search for a flight from KOA to LAX. To be as close as possible to our trip, I will look for a flight on Tuesday October 29th. Again, make sure to search for the number of passengers you need (3 for me), it defaults back to 1.
YAY!! There is a flight that meets our needs!!
Make note of the information we need. Tuesday October 29th, 1:08 PM, Flight 58.
Now, we actually go to British Airways to find the flights we want to book and ensure they show up there. Normally, they seem to show up well for American Airlines.
I mentioned using Alaskan Airlines before. You have to go through a similar process to this, but I have not done it. Also, you cannot book the Alaskan flights through BA’s website, you must call them. I didn’t want to do that.
To see the rewards flights on BA, you are required to sign into the BA Executive Club. You are not required to have the points in your account to search, just be signed in. From the main page, select the drop down “Book”, then select “Book a flight with Avios”
On the search screen, select the From, To, Depart, Return information to match our AA flights. Select Economy Class and the number of Passengers and click “Get flights”
Note that the drop-down calendar on BA starts the week with Monday, not Sunday. Ensure you select the right dates, it’s easy to pick the wrong one and get all messed up.
On the results page, select the Outbound and Inbound flights that match the times and flight numbers we found on AA.
Once you have selected the flights, you will see the total at the bottom. As you can see the total for 3 seats is 78,000 Avios (26,000 per seat). For some reason the total displayed only shows the taxes and fees for 2 seats.
The note states that the exact cost will be displayed after you click “Continue”. So, after clicking on “Continue” we see:
That I don’t have enough Avios to book these tickets, 😊. And the total now shows the correct cash total for 3 seats ($33.60). I don’t keep many extra points here, so I can use them elsewhere. If I had enough, I would then continue on and book the flights by entering the passenger information and so on. After the are booked you handle seat selection through AA which can be accessed by BA through a link in “My Bookings”.
Now, where can I get 78,000 points in my Avios account? I’m not going to go into all the details on that in this post. I intend to have more posts later specifically on that topic. However, in short, I had Chase Ultimate Rewards points to transfer. British Airways is a transfer partner with Chase Ultimate Rewards, American Express Membership Rewards, and Marriott Bonvoy Rewards. All these points can be moved to British Airways and used to book flights.
Now we have to get to LA. As you can see, the flight out is early in the morning and the fight in returns late at night. Depending on where you are flying into LAX from, you will need to determine if you can fly in/out on those same days. Flying from El Paso it’s not an option, and flying with kids, I wouldn’t want to force the even earlier start to the first day or later end to the last day.
So, we will look for flight to LA on the 19th, and out on the 30th. This is done by a routine search on the Southwest website. We didn’t book with points, but if you have them, it is straight forward to do. Southwest is a partner with Chase Ultimate Rewards. The Southwest Rapid Rewards system is a fare-based system, meaning there is no set rate for a specific route. The more the cash rate, the more points it takes.
Searching for flights on these dates, I see that the Non-stop flight from El Paso to LAX is $12 more per seat than the cheapest flights. To me, that’s a simple decision. Pay an extra $36 to spend 3 hours less in airports with two kids? YES, absolutely!! But if you want to save every penny for other things, there is a chance to save some.
On the return flight, the Non-stop is the cheapest, so no decision needed. We actually have two return flights to choose from at the same price. With kids, simple choice, the morning flight. No way I’m doing the late night one if I can help it.
The total cash price for 3 would be $694. As I described earlier, when we did this we were able to reduce this by $200 using gift cards purchased with our American Express Gold cards, and another $300 using the travel credit from Vicky’ Chase Sapphire Reserve card. That would bring this hypothetical trip down to $194.
That would put the total cash price for all flights for 3 at $227.60. I classify that as a win!!
If you had points to use on Southwest, these same flights would be:
For a total of 44,121 points and $33.60. For the entire trip on points, we would need 122,121 points and $67.20.
Hotels
Woo…let’s take a deep breath now. I told you that the flights were the more complicated part.
Now, we can move into the Hotels, which will be much easier. Trust me.
As previously discussed, we are using Marriott and Hilton points. We had ~175,000 Marriott points and ~100,000 Hilton points.
Since we are flying into and out of Kona, we would like to either begin or end our trip in Kona (spoiler: we did both)
Finding this availability is straight forward. Go to Marriott’s website and log in to your account. Click on the “Find & Reserve” menu on the top to search. This gives you the option to search for points stays. Set your destination to Hawaii, USA, select your dates, select “Use Points” and click “Find Hotels”.
For this example, we don’t need to be any more exact than Hawaii, as there are only six Marriott properties in Hawaii. If you would like you can be more exact and tell it Kona. Also, at first you can just look for the entire duration of the stay 10/20-29. If there is availability for the entire time, you know you have flexibility.
A list of the six available hotels comes up. From here you can see the rates. If rewards stays are available for the entire stay, it will show the points/night, if not it will only list a cash price or say not available. The Courtyard King Kam Hotel is listed at 25,000 per night. Clicking through confirms that it has several room types available for the duration.
Since we get the 5th night free, we could stay for all nine nights for 200,000 points. Of course, we don’t have that many, but it’s a start to know this information.
Next, let’s check on the Hilton availability. There are more Hilton hotels available, so here I recommend searching in Hilo, HI. We can do that same kind of search for the entire duration of the trip. Select the box labeled “Special Rates” and check the box labeled “Use Points”. Then click “Find a Hotel”
This shows us the Grand Naniloa Hotel. A Standard room for these dates is currently showing for 46,000 – 50,000 points per night. The Hilton points don’t tend to go quite as far per point from my experience.
With this information, we know we need to stay for longer in Kona than Hilo. Also, to take advantage of the 5th night free, we need to stay for at least five consecutive nights at the Marriott.
What we decided to do was stay for the first five nights at the Marriott King Kam. This cost 100,000 points.
We followed this up with two nights in Hilo. At the time we booked this, I was able to use 40,000 points per night, for a total of 80,000 points.
Then we returned to Kona for the last two nights back at the Marriott King Kam. This cost 50,000 points.
That’s it for the hotels in Hawaii, but let’s not forget that we need to stay in LA for a night on each end of the trip.
We previously decided to stay at the Crowne Plaza, LAX for both nights. This hotel is near the airport and has a free shuttle.
The Crowne Plaza is a brand in the International Hotels Group (IHG). We had about 65,000 IHG points at the time and a free night certificate.
To search for these rooms, you sign into the IHG website. For this one, we can search for LAX, to find the nearest hotels, select the dates. You can either select a “Special Rate” to use points, or just change it on the top of the results page.
The Crowne Plaza is the nearest hotel to LAX at a point cost of 35,000 per night. There are a few hotels that are 25,000 – 30,000 points, but we picked this one due to the location.
For the other night we used a free night certificate that we earned by having an IHG credit card. With this card, we get a free night each year anniversary of having the card. To redeem the night, we go to our My Account page on IHG. Your points total is on the top left of the page, where it will also link to redeem any free nights you have.
On the next page it has a link to book your night. You search for the location and dates, and book it like you book the rewards night.
With these two methods we booked our LA nights.
We now have all of the hotels booked for a total of:
120,000 Marriott Bonvoy points
80,000 – 100,000 Hilton Honors points
35,000 IHG points and a free night certificate, or 70,000 IHG points with no free night.
You can earn these points directly, or transfer points.
Marriott is a transfer partner of Chase Ultimate Rewards and American Express Membership Rewards.
Hilton is a transfer partner of American Express Membership Rewards.
IHG is a transfer partner of Chase Ultimate Rewards.
Rental Car
Now, you don’t need a rental car for all destinations, but I really recommend it for the Big Island. The Island is pretty…well…big. Some of the best locations; parks, beaches, etc. are spread out. And to get from one side of the Island to the other (Kona to Hilo, and back) is a couple hours drive.
The company you choose is your choice, the rewards are not the most useful, so just find the cheapest that you trust. We like National Car Rental, but are not dedicated to it.
The one hint for Hawaii is that the car rentals are a little higher than many places since it is an island so the supply is somewhat limited. To get the best rate took some monitoring. I booked a car at the cheapest rate I could about 5 months ahead of time.
Make sure the agreement has no cancelation penalty. This makes sure you have a reservation in case it turns out to be a popular time with limited availability as the rates will go up.
About a month before the trip, start checking the rates again. If you find a better rate, book it and cancel the first one.
Doing this, our initial reservation was for $565 for the duration of the trip. When I rebooked a month out, the price had dropped to $357. The rate after that went back up slightly, and higher than the original price about a week out.
Conclusion
Well that’s how we planned out our trip. This was a lot longer post than I thought when I started, but it covers the entire planning process.
For any of you that made it all the way to the end of this post:
THANK YOU!! You’re the people I’m really targeting with this entire site.
If you liked this, please like the Facebook page, and share our content with your friends.
See Part 2 Here to read about the first part of the trip.
