Tips to Get My Friend Ed to Hawaii

My friend Ed Pizzarello of Pizza in Motion fame, hosts a podcast called Miles to Go. On his show he often laments/ humblebrags that he has never been to Hawaii.  I almost think that people on his show are so amazed by that fact that he takes it as a point of pride to have never been there.

Ed, sure that’s fine for you, but think of the children!  Sure it will look good on their college essays to list the hardship of never having been to Hawaii, and that’s not a bad strategy to get them into Harvard, but look at the life experiences you are denying them.  They may harbor resentment for the rest of their lives.  You may be labelled as a bad father.  Sure, you take them to Disneyworld like ten times a year, but still…

Most of us in the frequent flyer community consider this crazy since that is a prime destination for users of points and miles.  My wife and I lived there for three years and have returned every year to vacation at one of the islands. We find it very easy to get there and always get there with a great deal.  Today, I am going to lay that strategy out for you and see if you won’t be tempted.

Items required to make this work for a family of four:

Two Bank of America Alaska Airlines credit cards

Two AMEX Aspire Hilton credit cards

480,000 Hilton Honors points for two rooms for five nights

Optional – Gold Guest Upgrade Certificates

Optional – AA or AS Lounge membership

Now, Ed, you may be questioning the first item on the list.  Alaska Airlines? But I live in D.C., not Seattle. Actually, Ed, you might be surprised how much AS has expanded in the last few years.  They fly from all three Washington airports, BWI, DCA, and Dulles to most of the West Coast and then have flights from there to all the major Hawaiian islands. Here is the route my wife and I flew a few weeks ago.

Ed, I know you are concerned with a 10-12 hour flight to Hawaii.  Alaska also allows you a free stopover on their flights. One of my favorite ways to get to HNL from WAS is to fly BWI-SAN, spend a couple of days in San Diego, and then SAN-HNL a couple of days later. You could also do the same for LAX or SFO. In the summer, SEA is also a good stopover. Likewise, you can do the same on the way back.  This breaks up a long journey and is probably easier for the kids to handle, plus they get to see another city or two.

 

Why Alaska and no the other airlines? Because of one of the best CC benefits out there – the BoA Alaska Airline CC’ Companion Certificate.  As the name implies, this is a $99 ($122 with takes) ticket for someone travelling on exactly the same itinerary as you.  Right now, BoA has a deal where they will they are waiving the $99 fee the first year so that companion ticket only costs the $22 in taxes. So it really is two tickets for the price of one.  Ed, if you and your wife each get this CC, your family of four flies for half price (~$1800). Don’t forget to have AS FF accounts as each person earns full distance-based miles for these tickets. At about 10,000 miles round trip, that’s quite a few very valuable AS miles. My being a MVP Gold and my wife a MVP Gold75k, we earn 100% and 125% bonuses, respectively, on these trips meaning almost enough for a free award ticket for this one flight.

If you have a REALLY good friend, they may also give you a Gold Guest Upgrade (GGU) that they get from being an AS Gold. You need to select that from the pull down menu when searching for flights.  Look for flights with blue “F” boxes. If you are fortunate enough to find a flight with both legs showing as upgradeable that still only takes one GGU. Note that these fares may be slightly higher but way cheaper than outright buying First Class as shown below.

So that’s how to get there, but what about an inexpensive stay once you do get here? Here is a strategy for that with Hilton.  The AMEX Aspire card came out about a year ago and offers an interesting way to maximize value.  The card is $450/yr., but comes with Hilton Diamond Status and a $250/yr. credit for incidentals (everything but the room rate) at Hilton hotels. It is really meant to offset the ludicrous resort fee of $50/night, but here is a better way to use it.  Hilton does not charge the resort fee if you stay on points, meaning you can apply that credit to restaurants, surf lessons for your kids, or your morning coffee at Starbucks.  The most economical strategy is to get a room for four nights on points and then Hilton will give you a fifth night free. This applies whether you use points or cash, but let’s stick with points for now. We recently stayed at the Hilton Hawaiian Village for 240,000 points for five nights. That might seem like an incredible number of points, but Hilton points are very easy to earn.  In fact, the sign up bonus for the Aspire card is 150,000 right now so you are already over halfway there just with that.

 

Another benefit from the Aspire card is a $250 credit for airline incidentals including lounge membership. That will almost pay for an annual lounge membership for AA or AS (which also gives access to AA lounges) and make your voyage a little bit easier, especially with a family.

Your new Diamond status should get you an upgrade at the property and also comes with the benefit of a $10/ person (max two)/ night for food and beverage at any of the ten places to eat on the property.  For a five night stay this worked out to $100 off the bill. Note that they simply take off the $100 rather than force you to spend at least $20/day. Here is our recent bill illustrating what I am talking about.

And then my AMEX bill showing the credit. Note that I had used $31 of the credit earlier in the year, but you should get the full $250 if you follow this plan.

So there you go Ed, an inexpensive way for you to take the family to Hawaii. This plan would also work with going to Maui or the Big Island, although most of the things your kids would like are probably on Oahu. Make sure they try the Dole Whip at the Dole Plantation!