Posted in Travel Planning

What are the Odds!

If you follow my blog, you may be aware that I put a plan in motion this year to travel a lot on Southwest Airlines because I wanted to get the most bang for my buck from my Companion Pass.  I took my first trip with my daughter in May to Portland Oregon. We are still working out details for a trip to Texas in September to visit my son and I have been so excited that Mark and I recently pulled the trigger and decided to take a trip to Hawaii in October.

So Happy to be going to Hawaii!

On May 31st I published a post titled Planning a Big Trip Can be an Emotional Roller Coaster not realizing that there would be events popping up pertaining to our Hawaii trip that really illustrate what I meant by that.

Incident #1

I looked up prices and lined up the flight segments for Hawaii on Friday, May 31st. You have to fly in segments for the Hawaii Routes as they only leave from California.  So we needed to get from DTW to OAK and then OAK to HNL and back.  At that time, I was 3,000 points shy of being able to book the entire trip with points.

I was very excited to be so close and started sifting through my loyalty programs looking for points that I could transfer to my Southwest Rapid Rewards account (preferably at a rate that didn’t want to make me barf).  I decided to move 10,000 Marriott points which would give me 3,333 more Southwest points at the 3:1 transfer ratio. It took me a day to figure out my plan and a little over a day for the transferred points to make it to my Rapid Rewards account. On 6/2 at 11:30 am the points finally popped up, so I started the booking process. All the flights were the same as when I priced them except one. The first key segment of the OAK – HNL trip had gone up by just over 1200 points. Choosing a different flight was not an option, because getting the segments to line up is kind of  tricky.

I had to remind myself to Breathe…..not to panic because I could still pull this off.

My solution was to book the most important first 3 segments right then in order to lock in the prices. The last segment OAK – DTW was already messy because it didn’t line up very well for the connection. Since there were a lot of possible flight options all at the same price….I thought we would be ok waiting to book this segment. I need to earn the points before my Southwest credit card statement closes mid June. Just to be safe, I also requested a points transfer from Best Western to Southwest (5,000 BW points converts to 1,200 SW points).  I need to be 100% sure there will be enough points.


I feel like I am in a pretty good place with my solutions for this matter, barring any other unforseen issues!

Update: The additional points finally hit my account 6/18 and I was able to book the last segment of our trip 😀

Incident #2

The next part of my scheme that didn’t go quite as I planned was securing some Hyatt points from the Daily Getaways annual promotion.  Daily Getaways is a month long promotion by the US Travel Association that offers a wide arrange of deeply discounted deals on travel items like car rental certificates, hotel points, and hotel stays and attractions.

I should start by saying that I had used most of my Hyatt points during my trip to Portland with Maggie.  So I have about 7,500 left to play with.  Since we would be staying 6 nights total in Waikiki, I decided to split that into 2 hotels stays of 3 nights each.  The first 3 nights we would stay at the Hyatt Place for 12,000 points per night and the second 3 nights would be some place kind of fancy and on the beach (still to be determined).

The Daily Getaways had an offer only available on 6/3 at 1 pm for 30,000 Hyatt points at a cost of  $330.  It was a great deal.  That would give me 37,500 points which would cover the 36,000 points needed for our 3 night stay.  In theory, that would make each night cost about $110.  I was very happy with this plan and was online early just waiting to buy my points when they went on sale.  I started trying to purchase them at exactly 1 pm,  but was not able to get them or any of the other 3 Hyatt points offers (24,000 points, 40,000 points and 72,000 points).  They literally sold out in about 1 minute flat.  Jinkies!


I felt my heart sink a bit as this plan went down the drain.  Hyatt had a 40% off points buy discount going on, but when I checked the prices were much higher than the Daily Getaways Deal.  Now I would have to think up a plan B.  After wringing my hands and fretting a bit, I decided it is time for Mark to get a Universal Rewards card with a sign up bonus of enough points to transfer to Hyatt.

I am feeling a bit of stress needing to work fast setting up the new card and spending enough to earn the points bonus.  It will be close.

Incident #3

On 6/11 I was drinking my morning coffee and reading some Travel pieces on Twitter when I ran into an article by The Points Guy that stopped me in my tracks.

Major Waikiki Beach Improvements Promised in New Hawaii Budget

I felt kind of sick as I read this article about how Hawaii was going to be doing much needed repairs to their oceanfront Waikiki seawall starting late this summer into the fall.  This article included a link to the AP with more information on the precise area planned for the renovations.


News: Hawaii budget includes $13M for Waikiki Beach restoration

The $13 million is sufficient to shore up the Royal Hawaiian seawall between the Waikiki Sheraton and Royal Hawaiian hotels and return a seawall to Kuhio Beach, which officials said have been failing for years.

Although I am really happy for Waikiki to get these improvements, it figures that the work would be done during our once in a lifetime visit. Oy!

The Need for Speed

Here is the good news (at this point can there be good news) I have not made my hotel reservations yet so I can be somewhat adaptive.  But my guess is that everyone heading to Hawaii the same time as us that has read about this construction, is now either thinking about changing their hotel reservations or are looking at booking the same properties I am.  This means I will have to make some quick decisions before prices go up on the properties less affected by the construction or before they book up completely.

Now I am feeling the pressure as if the Ka the snake has me tightly wound in it’s coils……..Ahhhhhhhhhh!

I have decided to stick with my plan to stay the first 3 nights at the Hyatt Place.  It is not beach front and still helps me meet my budget. Just gotta get to getting on those points!  I just have to reconsider my choices for the remaining 3 nights.

Ko’Olina beaches don’t look to be affected by the renovations. The properties there are pretty pricey compared to what I can get us in Waikiki, so staying there may not be an option.  I was watching a Yellow Productions Video Guide last weekend about the Ko’Olina area which showed that besides the fancy hotels, there are some great public beaches.  We could totally take some day trips there or to the North Shore if the construction ends up being terrible.  This does, however, sway my decision on whether or not to rent a car during our stay.  (Car rental post coming soon).


No need to panic yet right, we don’t really know what stage the project will be at during out late October stay.  Maybe it will be wrapping up ahead of schedule and not that bad or it could be running behind and awful.  There is just no way to tell!


Roller Coaster!  

Which brings us back to the theme:  The Emotional Roller Coaster of Planning a Big Trip!  Boy, this one has been bumpy, fast and with plenty of twists, turns and nose dive hills. I have experienced 3 strikes already in less than 2 weeks of our planning. Yikes!  And as a planning team of 1 (because Mark doesn’t get too involved with that part) I am carrying the brunt of the stress until I get all of our reservations set.

The key take away here is that I am not giving up on this trip no matter how many speed bumps pop up along the way.  Each time a barrier presents itself, I just have to stop, compose myself then look at what other options are out there to keep the plan moving forward.  I have taken very few trips that have gone off exactly as originally designed.   I mean last year we still ended up having a great trip after spending 31 hours at DTW airport instead of exploring London…If you can deal with that, you can make it through just about anything.  You just have to go with the flow and keep the faith.

Fingers crossed that once I get off the planning roller coaster, this is all going to work out fine and be a super amazing vacation!


Dream, PLAN, Save, Adventure and watch out for speed bumps!