Trip Planning: Hawaii March 2017


If you've been following along in my blog posts, you know that we already have some 2016 travel plans in place, with perhaps some more on the horizon. We had initially wanted to plan for a Spring Hong Kong 2017 trip, but finally made the decision that it wasn't a good choice to go simply to take advantage of lower award prices pre-award chart devaluation.

Then, I unexpectedly won 2 free round-trip tickets from Alaska Airlines! What is especially great is that Alaska has lots of flights and availability to Hawaii, so this put us on the trajectory to travel plan for Hawaii instead.  I wrote a guest post for Frugal Vagabond last December on "The Anatomy of a Travel Hack", but this post is to show how I actually travel plan for our family.



Having been to Hawaii many times when I was younger, but only to Honolulu, I wanted suggestions as to which other islands people recommend visiting. I posed my question on Facebook to friends and family and there was an equal amount of votes for both Maui and Kauai. My wife Rachel has never been to Hawaii. I figured that it might be good to start our trip off with the city hustle and bustle of Honolulu, and then end with a bit more quiet time in Kauai. Maui we will save for another time, as it seems like an island worthy of its own visit.

Next, I needed to figure out our dates of travel. Our Alaska Airlines roundtrip vouchers expire next March, so that basically set our timeline for us. With our annual family vacation coming up in October, then followed by the holidays, the closer we are to March the better, to allow us to save up that paid vacation time! These vouchers also allow us to have an open-jaw, meaning we will be able to arrive in Oahu and leave from Kauai. I will book 2 1-way inter-island flights using either United or American miles for 5,000 each on Hawaiian Airlines.

Taking inventory of our hotel points stash, we have a good amount available for either Starwood, Hyatt, or Hilton accommodations. Most of our Hilton points came from my recent app-o-rama, which is particularly good timing for next year's trip. I then searched on Tripadvisor for the best reviewed properties both in Honolulu and in Kauai. Hilton has an enormous footprint in Waikiki, with many of their properties rated highly, so that made the decision easy. However, only having a certain number of points available, I had to balance between choosing an affordable property versus the fanciest/best rated property. If the amount of points were not a restriction, I most definitely would have wanted to put us up at the Hokulani Waikiki, rated #10, but it would have cost us 132,840 points A NIGHT! Uh, no. I ended up settling on the Hilton Waikiki Beach, rated #24, but only requiring 40,000 points/night. Being partial to the Starwood brand, I decided we couldn't go wrong with staying at the St. Regis Princeville in Kauai, rated #1, especially since we had such a fantastic experience at the St. Regis Bali during our 2014 Asia Trip! If not for the 30,000 points/night at the St. Regis, we probably would have opted to stay at the Moana Surfrider instead of the Hilton Waikiki! Next time.

Obviously, if you are booking either your flights or hotel stays with cash, you will have to do the same dance of weighing price versus quality/best reviewed/where you want to stay.


Status & Benefits

I am SPG Gold due to spending at least $30K/year on my American Express SPG card. This status comes with in-room internet, upgrade to an enhanced room at check-in, and choice of a welcome gift. I am also Hilton Honors Gold, but waiting on Hilton for a status match to Diamond. Both HH Gold & Diamond get late check out, internet, complementary access to fitness facilities, and upgraded rooms, if available. The only difference between HH Gold & Diamond is the complementary continental breakfast for 2, access to the Executive Lounge, and perhaps more consistent room upgrades. Both Starwood & Hilton programs have the "5th Night Free" for all standard and award bookings, so that saves us some points on both of our stays. 

Again, we would preferably book with Starwood if we had the points, as their Gold program is much more consistent, upgrades more reliable, and overall service and quality a notch above the rest. However, one good thing about choosing the Hilton Waikiki is that this property does not charge the daily $30 resort fees ($150 for 5 nights) that many other hotels will charge!

Since we will be flying Alaska (Rachel kindly requested that I not book us in Economy) I will be looking to leverage us into First. Alaska has been known to generously status match the Southwest Companion Pass to Alaska MVP Gold 75K. MVP Gold 75K comes with complementary Board Room lounge passes, and most importantly unlimited First Class upgrades for you and a companion. If I status match November or later, our MVP Gold 75K status will last through 2017, which will be just in time to upgrade our flights to Hawaii! 



I have not actually booked our flights or hotels at this point. Due to the status' that I hold, it is prudent for me to book everything under my accounts. At this point, I am still some points shy for both hotel stays, but the good thing is that since I am planning this far out in advance, we have time to accrue them! Another nice thing about winning those roundtrip travel vouchers is that as long as there is availability on those flights, I can book as close to 2 weeks out. So it makes sense to nail down our lodging first before booking our flights.



When planning a trip, always start over at TripAdvisor. Not only do they have loads of reviews on hotels, but lots of good information on things to do as well. From there, take inventory of your cash or points pile, and make a list of where you would like to stay, along with their associated costs so that you can weigh the cost/benefits. Lastly, take into account what statuses you already hold or are close to holding, as these may further enhance your stay or help guide you towards making a decision about where to stay. The further out, time-wise, you are in planning your trip, the more options you will have in terms of flights, accommodations, obtaining statuses, and saving up the cash/points required to meet your travel goal! 

We cannot wait to enjoy the warm sunshine, blissful breeze, and rugged natural beauty of the Hawaiian Islands next spring! Hope this insight into how I plan our trips was helpful! Now get planning!

*Where are you planning to travel next? What is your travel planning process? How is it different or similar to mine?

*Photo: courtesy of