Piecing Together A Big Hawaii Trip – The Planning, The Cost & The Issues

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A few weeks ago the family and I enjoyed a great 14 night vacation in Hawaii and, unsurprisingly, the trip planning was mostly my responsibility.

I actually really enjoy planning trips, finding great fares and researching destinations but every now and again a trip comes up for which the planning is a little bit more complicated and takes considerably more thinking and compromising than most – this was one such trip.

The Trip & The Constraints

The whole trip was based around a couple of timeshare weeks I own in Hawaii, the school vacations and 5 travelers who would all be starting the trip from Europe.

Broadly speaking the itinerary for the trip looked like this:

  • Europe – US West Coast (1 night layover on the West Coast)
  • West Coast – Maui (7 nights on Maui)
  • Maui – Kauai (7 nights on Kauai)
  • Kauai – US West Coast (1 night layover on the West Coast)
  • West Coast – Europe
All the planning was worth it just for the sunsets

The biggest constraints were the dates of MJ’s school vacations and the dates that I could book the timeshares and the two didn’t go together very well.

In fact, they went together so badly that it turned out that there was only one set of dates which would work if we wanted the trip to pan out as I’ve set out above. That was very bad news for me as I was hoping to book award flights or at least get a very good deal on a cash fare and flexibility is usually key with both of those things.

Ideally this is what I was hoping to book:

  • Reasonably priced Business Class flights for MJ’s grandparents (at least for the transatlantic segments).
  • Business Class award flights for Joanna, MJ and me (at least for the transatlantic segments)
  • Economy Class awards between the West Coast and Hawaii if no Business/First Class awards were available
  • Good Economy Class fares between the West Coast and Hawaii if awards weren’t available.
  • A cheap inter-island flight between Maui and Kauai on Hawaiian Airlines

In hindsight I was never going to achieve all of that but, considering the constraints and the issues, I don’t think I did too badly – see what you think.

The Bookings & The Costs

Joanna & MJ

Joanna and MJ’s flights were the first I booked as I somehow managed to find 2 roundtrip Iberia Business Class awards between Madrid and LA for the exact dates we needed – that was nothing short of miraculous!

There was no onward award availability (in First/Business or Economy Class) and there was no award availability left for me at all but that wasn’t all that important – I was getting Joanna and MJ across the Atlantic (in both directions) in comfort so that was a win.

The awards each cost 115,000 American Airlines AAdvantage Miles + $139.66 in taxes/surcharges.

The timing of the flights meant that they would need a Madrid airport hotel for the night before their flight to LA ($80) and they would also need roundtrip Economy Class flights between London and Madrid ($104 each).

The hardest part of the booking was getting them between LA and Hawaii.

I searched for awards on a near daily basis and set ExpertFlyer alerts to make sure I didn’t miss out but months went past with no luck at all. Cash fares were ridiculous for the dates we could travel (approximately $1,000 each for LAX-OGG//LIH-LAX) but they weren’t really moving so I was happy to keep waiting to see if anything else turned up.

Eventually American Airlines released a number of Economy Class awards on its Kauai – LAX flight so I jumped on those and booked them using Avios.

The awards each cost 12,500 Avios + $5.60 in taxes.

That left just the Los Angeles – Maui segment (I’ll come on to the inter-island flight later) and, as we got closer and closer to our departure date the flights were filling up (based on ExpertFlyer and the AA seat maps) and, unsurprisingly, the prices weren’t coming down.

We took the decision to suck it up and pay for a one-way Economy Class fare for Joanna and MJ (a painful $434.20 each).

A few weeks before we were due to depart I noticed a serious issue with Joanna & MJ’s award bookings (I wrote about it here) which resulted in a last minute change of plans…for the better.

Rather than having to fly between London and Madrid to catch their award flight Joanna & MJ ended up flying direct from London with American. The extra taxes (thanks London!) cost $301.70 in total but the journey was a lot simpler.

The Final Bookings for Joanna & MJ:

  • LHR – LAX – LHR (Business Class): 115,000 AAdvantage Miles + $290.45 each
  • LA – Maui (Economy Class): $434.20 each
  • Kauai – LA (Economy Class): 12,500 Avios + $5.60 each

Total Cost: 115,000 AAdvantage Miles, 12,500 Avios & $730.25 each

MJ’s Grandparents

One of the many cool things about MJ’s Grandparents is that they’re always willing to try out different things and things that perhaps some would shy away from in the interest of an easy life.

It was that open-mindedness to travel bookings that meant that, even though they’re based in the UK, they were more than happy to consider starting the main part of their trip from continental Europe if it meant getting a good Business Class deal……and boy did I find them a deal!

With Joanna & MJ booked to fly via Los Angeles I really wanted to route the grandparents through the same city and, within a month of booking Joanna & MJ’s transatlantic flights, I struck gold.

For a period of 48 hours last May Air France offered a staggeringly good Business Class fare between Milan and Los Angeles – £1,194.40 (approx $1,600) each.

Sure, the fare only got them as far as LA but there was no way we would be passing up on a transatlantic Business Class fare as low as $1,600 on a carrier with a very good Business Class product (as long as you choose your flights carefully).

The key here was to make sure that the Paris – Los Angeles sectors were booked on to Air France’s 777-300ER aircraft (reviewed here) and not on the airline’s A380.

While Air France’s 777-300ER aircraft offer a great reverse herringbone Business Class cabin set out in a 1-2-1 formation the airline’s A380’s offers antiquated angle-flat seats in a 2-2-2 layout – the Air France A380 Business Class cabin is definitely one to avoid.

Ensuring that I booked the 777-300ER meant a slightly longer layover in Paris on the outward journey but, considering what was at stake, the layover was well worth it.

Ait France 777-300ER Business Class – Image Air France

I had the same issues getting MJ’s grandparents to/from Hawaii as I had with Joanna and MJ so they too ended up booking Economy Class on the Kauai – Los Angeles sector with Avios (12,500 Avios & $5.60 in taxes each) and the Los Angeles – Maui sector with cash ($434.20 each).

The Final Bookings for MJ’s Grandparents:

  • MXP – CDG – LAX – CDG – MXP (Business Class): $1,600 each
  • LA – Maui (Economy Class): $434.20 each
  • Kauai – LA (Economy Class): 12,500 Avios + $5.60 each

Total Cost: 12,500 Avios & $2,039.80 each

Note: There were positioning flights required to get to/from Milan but as I didn’t book those I can’t say how much they cost.

A highly endangered Hawaiian Monk Seal having a rest on a beach in Maui


I was sorely tempted to book the same Business Class fare as the one I found for MJ’s grandparents but a combination of wanting to keep costs as low as possible and the fact that I had 4 American Airlines systemwide upgrades in my account tempted me to look elsewhere.

American Airlines Economy Class fares (for all but the Hawaii inter-island segment) originating in London were a little under $1,750 and there was no way I was about to pay that much for an Economy Class fare (I frequently pay considerably less for Qatar Airways Business Class!)…so I broadened my Economy Class search to include continental Europe as a starting point.

With most of Europe now in play I found a very good fare originating in Paris and ending in Copenhagen giving me the following flight itinerary:

Paris – London – LA – Maui // Kauai – LA – London – Copenhagen

That’s quite a series of flights (in Economy Class) and when you add in the fact that I’d have to position to Paris and get back to London from Copenhagen too this wasn’t exactly a dream come true for me…but at $997.18 for all but my positioning flights I had to book it.

Here’s what the positioning flights cost:

  • London – Paris (Economy Class): 4,500 Avios + $27.50 taxes/fees
  • Copenhagen – London (Economy Class): 4,500 Avios + 26.95 taxes/fees

Because I had to catch an early flight out of Paris I needed a hotel at CDG the night before my departure – the Ibis Styles was basic, but it did the job (cost was approximately $100).

Total Cost: 9,000 Avios & $1,151.63

I was placing my comfort in the hands of the upgrade gods (especially for the overnight flight between LA and London) but the considerable savings were just too good to pass up.

The best news, however, was that my London – LA and LA – London flights were the same ones that Joanna and MJ ended on so the inconvenience of us being split up was minimized.

The Intra-Island Flight

There’s only one choice of airline if you want to fly non-stop between Maui and Kauai and that’s Hawaiian.

The flight time between the two islands is an insignificant 35 minutes so you’d probably expect me to say that I booked us all into Economy Class while accepting the fact that we’d be boarding near last (none of us has airline status that carries weight on Hawaiian) and sitting in somewhat cramped conditions for a while…but that’s not what I did.

We had quite a bit of luggage with us on this trip and once I worked out that the cost of a First Class fare (which includes 2 pieces of checked baggage) was only $25 more than the cost of an Economy Class fare + baggage fees it wasn’t hard to decide what fare to book.

Add to that the fact that I’ve never tried out Hawaiian’s intra-island First Class cabin (so I got a new cabin to review) and there was never any chance of me booking anything other than the front rows.

The Hawaiian Airlines First Class fares cost $159.10 each

Bottom Line

I’ve booked a lot of trips in my time but this one probably took more planning and more patience than most.

When you have a number of dates you can work with there’s usually at least a few options you can consider but when you’re down to just one set of dates that work for you things can be tough.

All in all this wasn’t the greatest deal I’ve ever booked by any stretch of the imagination but it was still a pretty good one (in my opinion). I managed to get MJ’s grandparents across the pond in a great deal of comfort and at a very good price and I got Joanna and MJ to and from LA in comfort and at a reasonable cost too.

I would have preferred to not have to spend cash on the flight from LA to Maui (it genuinely hurt to have to pay that much for that flight) but that was the only option we were left with so that’s just how things panned out.

As for what happened to me well, let’s just say I got a few reviews out of the trip…you’ll have to keep reading the blog if you want to know if I got upgraded or not 🙂