As I’ve mentioned in my cruise post last week, I was able to get my husband to agree to Hawaii family trip in 2020. It has been 12 years since I’ve been to Kauai, so it’s time, right?
A lot will depend on my parents’ health. You see, I plan to bring them here in June of 2020. If they can’t fly for whatever reason, we will have to go to Eastern Europe instead, which means Hawaii would be off. Obviously, there are many other factors as well. But for now, this is the plan, and I like to be “the gal with the plan” at all times.
Hawaii is an extremely popular destination for families in US. It’s also more expensive and relatively harder to plan than say, your average trip to Florida. But miles and points can definitely make it happen and in this post I’ll show you how. Even though going to Hawaii in 2020 is not a guarantee for us (nothing in life is), I wanted to take a look at what I have and plan my future credit card strategy accordingly.
Taking an inventory of current miles and points balances
Miles and flexible points:
1) 105k Southwest Rapid Rewards points.
2) 85k Membership Rewards points.
3) 20k Avianca miles in my account, and 17k miles in my husband’s account.
4) Around 53k Avios that should come my way in 2-3 months. See this post
5) 125k Jet Blue points.
Hotel points:
1) 130k Hilton points.
2) 54k Wyndham points.
3) 10k IHG points.
4) 6k Hyatt points.
Non-negotiables
When you are dealing with points or frequent flyer miles, the more flexibility you have, the better. Unfortunately, I won’t have any for this particular trip. I’m looking at going over the kids’ Spring Break, so the dates will be fixed. Additionally, in order to maximize our time in Hawaii, we will have to leave and come back on a weekend. I also plan to overnight in a west coast city on the way to/from Hawaii, so this will limit our time further.
Flying on a weekend always makes finding low-level airline award a challenge. So, it will probably mean redeeming miles and points at a higher level compared to weekdays, and I’ll have to make my peace with it. I also insist on having non-stop flights to the west coast as well as Hawaiian islands. So, no connections in Honolulu or Atlanta, thank you very much.
Also, all the flights will have to occur during daytime. My husband and I hate redeyes, so I’m willing to pay extra to get what we want. Plus, we are traveling with kids, which makes it infinitely more complicated anyway. Finally, I intend to split our stay between Kauai and Big Island, so that’s another non-negotiable factor. We don’t have to visit them in a specific order, so at least there is a little bit of flexibility there.
In no way am I suggesting that you should plan your Hawaii trip the same way. As I’ve said earlier, the more flexibility you have, the more likely you are to get a better deal via miles. I’m at a point in my life where I’m willing to pay extra to get what I want. We will still fly in economy, but I intend to look for the path of least resistance. That said, my goal is always to cover as much as possible via miles and points, so I can preserve cash.
Executing the plan
Believe it or not, even though my point balances don’t look all that impressive, I have what I need to cover this trip right now. Well, aside from car rental and excursions. Here are a few possibilities:
Flights
1) Assuming there is a low-level availability on American or Alaska Air, 50k Avios will cover 4 one-way flights to Hawaii from several cities on the west coast. LAX will be my best bet for American, since it’s the hub. Alaska Air offers quite a few routes to Hawaii from San Diego, San Francisco and several other airports. This is one of the better deals in Avios program.
2) My 2020 Hawaii hopes are mostly tied to Southwest. The airline has announced that it intends to fly to Hawaii by the end of this year, and Kauai and Big Island (Kona airport) were specifically mentioned. So, I’m hopeful that I can put my 105k Rapid Rewards points to good use.
Obviously, it’s impossible to predict how much fares to Hawaii will run in 2020, but I’m hoping for 15k points one-way during non-holiday weeks. So, my stash could potentially cover our one-way fare from Florida to Hawaii, though I would book two separate legs.
3) My 85k MR points transfer to a variety of frequent flyer programs. I wrote a post awhile back on some “sweet spots”, which I recommend you read.
Heads up! As of August 25th, Chase Ultimate Rewards program will no longer partner with Korean SkyPass.
Bye bye, 25k miles roundtrip redemption on Delta from anywhere in continental US. Honestly, not a huge loss due to roundtrip requirements and the hoops you have to jump through. I also understand that the transfer from Chase to Korean program currently can take DAYS.
Anyway, the best deal for us will probably involve Singapore KrisFlyer program, especially if I can get an overnight layover on the west coast included at no cost.
Finding low-level United flights will be challenging, so I’m not really counting on this to work. But if it does, we can potentially fly all the way to Kona/Lihue from Orlando and stop overnight in LAX or SFO for 17.5K miles one-way. Unfortunately, transfer to Singapore program is not instant (takes 12-48 hours), so that would make me very nervous.
Reader Tammie left this comment: “I have booked Singapore miles on United to Hawaii. Singapore only allows a maximum 4 hour layover on domestic flights (24 for international), so an overnight in LA would price as two separate flights.”
Like I said, we won’t have any flexibility on dates, so perhaps transferring to Aeroplan (instant) and paying 22.5k miles is a wiser choice. I could even utilize Avianca miles (also costs 22.5k miles on United) for one ticket, and book the other three via Aeroplan.
There is also a fairly recent development where you can redeem Singapore KrisFlyer miles on Alaska Air and pay just 12k miles one-way from west coast. This makes it an even better deal than Avios, though once again, the transfer is not instant.
Personally, I would prefer to transfer MR points to Avios program instantly and pay an extra 500 miles per ticket. Another benefit is that you can cancel and only lose what you’ve paid in taxes. Plus, if my plans change, I don’t want to be stuck with KrisFlyer miles that expire in 3 years, regardless of activity.
There is also a possibility to transfer MR points to Air France Flying Blue program and redeem miles on Delta flights. However, Air France now uses variable pricing, so it’s hard to say what the rate will be next year. But if there is a bonus on MR transfers at the time, it could make sense to go this route.
4) This is probably the worst deal of all, but Jet Blue points can also be used for award flights to Hawaii. Jet Blue partners with Hawaiian airlines, and you can see the rates here It costs 22k Jet Blue points to book one-way flight from/to west coast, assuming there is a low-level availability in Hawaiian program (should cost 20k miles). This is obviously a fairly high rate, but if the flight times are good, I will be willing to consider it.
Jet Blue program does have one “sweet spot” on Hawaiian: inter-island flights for 6k points one way. We will have to fly from Kona to Kauai, so I will probably go this route.
Hotels
I plan to redeem my 130k Hilton points, plus a small cash co-pay for three nights in a standard room at Hilton Garden Inn Kauai Wailua Bay
Few weeks before the trip, I will contact the manager and ask if we can pay extra to upgrade to a 1-bedroom unit (otherwise costs 98k Hilton points). Sharing one room with kids for few nights isn’t a deal breaker, but I’m willing to pay some cash in order to avoid it. If we go with Hilton option, I will renew my Amex Ascend card in September of 2019 in order to get free breakfast at the hotel, plus airline lounge access passes.
For Big Island I definitely hope to utilize my Wyndham stash. It appears that there are several vacation resorts in Kona area, and one or two of them are usually available via points as long as it’s a non-holiday season. A nice thing about Wyndham program is that 1-bedroom units are bookable for flat 15k points per night.
Future sign-up bonus strategy
As you can see, if all goes well, I should be able to cover this Hawaii trip with what I already have. That said, there is always room for optimization.
I was already planning to apply for Citi AAdvantage card in January of 2019, as soon as I’m eligible for the sign-up bonus. AA miles get trashed in this hobby on a regular basis, but they can definitely come in handy under the right circumstances. SAAver award availability will depend on the route and time of year, so don’t automatically dismiss this option without checking first.
For example, I was looking at award availability to Kona from Orlando for four people in March of 2019, and here is what I found:
Yes, for 20k AA miles per person (technically 18k miles via 10% credit card rebate) we could cover flights to Kona with an overnight stay in LAX included. This would be the best deal for me, hands down. Like I always say, there is no such thing as a worthless mile.
Click here to view various credit cards and available sign-up bonuses
Author: Leana
Leana is the founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.
I’d use my JetBlue points to lax or lgb then lax to Hawaii using sw points.
@Natasha I definitely hope to utilize Jet Blue Points, if at all possible. Unfortunately, Southwest will not be flying to Hawaii from LAX, at least not right away. I think there is just too much competition on this route. Ideally, I hope to use Southwest stash for one-way from MCO to west coast, and then to Hawaii. For the other leg, combination of Avios and Jet Blue Points, perhaps. Or maybe I’ll use AA miles, assuming I get approved for Citi AA card in January. Hopefully, something will come together.
Keep an eye on EndlessVacationRentals.com for Hawaii Wyndham properties. I snagged a dirt cheap week at Kona Coast Resort there a couple of years ago.
@Thedealmommy Yeah, I remember that! That was quite a deal you snagged. I’ll definitely keep an eye on it. Since I will only need 3 nights in Kona, burning Points might be the better option. I accrue Wyndham Points via their old card renewal benefit, so technically, each night in a condo will cost me only $69. So, that’s my benchmark. But I’m flexible, and don’t care where we will end up staying.
Just a note or two: I have booked Singapore miles on United to Hawaii. Singapore only allows a maximum 4 hour layover on domestic flights (24 for international) so an overnight in LA would price as two separate flights. Also I’ve been looking at delta availability using flying blue miles from SLC to Hawaii and there is very little to no availability over the next year. Not sure if that is the case with other cities but hopefully it will change going forward! Flying blue can still be a good option for delta flights…if delta releases flights!
Thanks for the blog. I enjoy it a lot
@Tammie Thanks for your comment and for your kind words about the blog. I’ve never personally dealt with Singapore program, so your data point is quite useful to me. I’ll update the post.
I’ve heard that there is a cutoff when it comes to layovers, but wasn’t sure how long. To be honest, Singapore program is not one I want to mess with anyway, so that’s the end of that option. My preference would be to burn Avios, Southwest and Jet Blue points and hang on to my MR stash if at all possible. We plan to go to Europe at some point, and I’m hoping to use MR points on Delta transfer for MCO-AMS route. But I’m getting ahead of myself, as usual!
Great minds think alike. Hawaii is calling my name for a family trip in 2020 also. I know a lot can change between now and then, but I’m going to start collecting miles and points with that trip in mind.
@Jennifer For sure! Doug has agreed to it, which is a miracle. He is slowly turning into an old man, so I want to go to Hawaii as a family before he changes his mind. 🙂 I did tell him that I would go to Europe with kids by myself in the future. He hates flying so much, especially redeyes to Europe.
We are planning a LA/Kauai/Honolulu trip in the summer of 2020. BUT we are a family of 6. I have already sketched out numerous scenarios but losing Korean Air/ultimate rewards threw a wrench into my plans. I have 270k aa but 6 tix is difficult! I am determined to make it happen!!! Love your blog – it’s truly a blog for families on budgets! Not many blogs like yours exist! Thank you!
Marsha, first of all, thanks for your nice words! I’ve truly poured my heart into this blog over the last 5 years, and I’m glad you are able to glean some value from the content.
Being based in LA (I’m guessing it’s LAX, not Lousiana? :)), you are in a great spot to pull off this trip. Don’t worry about Korean program. It has many quirks, like having to book a roundtrip award on Delta. Booking award tickets for six people will be tough, but not impossible. You can always pay for one ticket if that’s what it takes. Having this stash of AA miles will definitely be helpful. However, I recommend you look into collecting some Avios points because the same flights that currently cost 22.5K AA miles will run 12.5K Avios.
Better yet, invest in flexible points. Both MR and UR programs partner with Avios, so those are great options. Plus, with UR points you can book paid flights and get 1.25/1.5 cents per point, depending on the card you have. Your other decent option will be Air France program, for flights on Delta.
However, if you just want to burn AA miles, there is nothing wrong with that. I recommend checking few times per day because AA saver seats get released in batches, and not always when the schedule opens up. You just have to be persistent. Having flexibility in your dates also helps. Don’t hesitate to contact me if you have any questions. I bet you will be able to pull it off!
Thank you! You just gave me some extra tips! We are coming from Charlotte but want to fly thru Los Angeles and spend some time there. Love the Avios tips!!!
@Anonymous No problem! Avios is a quirky program, but it can be quite useful under the right circumstances.
To follow up on what Leana said–
Avios are indeed awesome, since BA/Avios has as many as seven seats available at a time on American, but only IF you can find availability. We’ve flown my family of 6 out of CLT quite a bit on Avios but on the last few trips we’ve been burning AA miles on account of the availability issue. Like Leana said, check the AA availability often and compare vs availability on the British Airways Executive Club site. If you want to stopover in LAX, you could consider doing Avios one-way (since AA doesn’t allow stopovers) and AA miles the other way.