Hawaii - May 2019 for 10 year Anniversary! Help!

Discussion created by thriftyscrooge on Dec 29, 2018
Latest reply on May 8, 2019 by iahflyr

Hello fellow MRI,


Happy Holidays to all; let's hope 2019 brings some stability and positives to the Marriott Experience for us loyalists, and 2018 is just a (bad) blip as far as the program goes.


So, next May the Mrs. and I are celebrating our 10-year wedding anniversary, and taking that long-talked-about trip to paradise, aka the Hawaii Islands :-). Being on the East coast has made Europe a lot easier to get to, and HI is up there with our recent trip to the Maldives in terms of travel time!


As a final hurrah from the old program, I emptied the points bank right before the merger and bought my (last?) 7-night Cat 8 travel package and booked the Wailea Beach Resort - Marriott in Maui for 7 nights in May. Our flights are booked - flying to OGG, and returning from HNL after spending a grand total of 15 nights in Hawaii. These are the only firm reservations at this time, and I've been debating on what to do with the remaining 8 nights that we have, since no other accommodations or inter-island flights have been booked.


After consulting travel blogs, several friends, colleagues and neighbors on their varied travel experiences to HI, I'm still at a loss for how to proceed, and figured I'd page some HI travel experts, (kharada46, and bejacob come to mind) to chime in... I've already read a few of the most recent, relevant threads (Looking for Hawaii input for 2020 ) so I don't want to waste anyone's time providing information that they already have in the past. That said, here is my situation:


1. Travelling with an almost 5-year old; can't do anything too strenuous (outdoor activity-wise), since I'll likely just end up having to carry the kid and wear myself out. Would like short family-friendly hikes, etc. no more than 1 mi.

2. We're foodies, so yeah... Waikiki/Oahu are definitely on the must-do list. Just not sure how long to spend on that island before we depart from HNL.

3. I'm torn between doing just Maui and Oahu or also a 3rd island for a few nights... I've heard a LOT of praise about Kuaui and the Big Island, although it seems to come from mostly the outdoorsy types.

4. Pools are a must wherever we go. The kid can't snorkel yet and the pool allows for supervised water play while we relax with a beverage! However, we love snorkeling, so thats something we'd like to do more of in HI.

5. If we do just Maui and Oahu, should I extend Maui by a few more days? If so, stay where I am, or relocate elsewhere on the island?

6. If I do 8 nights in Oahu, am I there too long? Also, should I stay a couple of different places on the island, or just AirBnb it in Waikiki and drive around? We'll have a car wherever we go.

7. If we do one of the other islands, how long should we plan for ..2-3 nights? I'd like at least 3-4 nights in Oahu if we opt for a 3rd island.

8. Wife gets sea-sick, so no island hopper cruise for us. We're more of the "stay on land, explore as much of the local culture as you can" types.


Sorry for the multiple choice format here... I understand everyone makes their decisions based on their own factors, but these are mine. I'm not tied to Marriott properties for this visit, although anything I can get on points to reduce the $$$ outlay on this trip is greatly welcome. I'm LTPP for next year, if that matters at all..I def. look for a complimentary room upgrade, and for free breakfast whenever possible. 


Great service, great concierges, and location matter. Personal connections to hotel GMs and golden key concierges are def. welcome, since I always communicate with the hotels well in advance.


Sorry for the broad strokes. Looking forward to an enlightening discussion and some sage wisdom from those in the know!


Cheers, and here's to looking forward to the year to come!