Old Jul 24, 18, 4:44 pm
  #1  
s0me0nesmind1
 
Join Date: Jun 2014
Location: HOU
Programs: AA Plat | Delta Plat | Marriott Gold
Posts: 21
Booking Award or $$ Trip to Hawaii - What are the best options?

Hello folks,

I'm planning on a vacation to Hawaii (Maui) and am trying to figure out the best means of booking my flight. We are looking for the least amount of segments as possible - and it will no doubt require at least 1 stop. All of the MileSAAver fares require 2+ stops, so those are a no-go. We will have a baby with us as well.

First, some clarifications:
  • Flying from Houston (HOU or IAH) to Maui (OGG)
  • 70,000 American Airline Miles
  • 90,000 Marriott Reward Points
  • 66,000 Starwood SPG Points
  • 320,000+ AMEX MR Points
  • I have Platinum with American Airlines
  • Travel isn't until late October
Here is my problem - I want to get there using American Airlines. Ideally, I would like to book coach and use some of my 40+ 500 Mile Upgrades to be upgraded to first. Perhaps I am crazy in that thinking?

So either way, here are my choices:

40,000 x 4 (Wife + I) = 160,000 AA Miles (Coach - Requires "Anywhere")
67,500 x 4 (Wife + I) = 270,000 AA Miles (First Class)
Buying direct round trip right now is roughly $950 each - and that's for coach.

Options

1) Buy coach - and hope for an upgrade. I I can use my Amex MR (1 spg per 3 MR) in combination with my Starwood (20,000 spg per 25,000 miles) to transfer over the miles needed - which would be roughly 80,000 miles with the 70,000 I already have.

2) Buy First Class direct with miles... It will probably cost me most of my SPG and MR points though since I will need 270,000 AA miles total

3) Put Amex MR to SPG - and convert SPGs to Marriott's and buy a vacation package in order to get most of the miles - I can either make up the difference with more SPG -> AA Miles for first class, or book the coach.

4) Maybe something I'm missing or another option? Maybe wait and see if the fare goes down? though the mile cost remains the same.
Any tips are appreciated, I'm pretty new to the whole game of moving around points - I'm usually the type that can spend them directly or convert them to cash (1:1 ratio)

Last edited by s0me0nesmind1; Jul 24, 18 at 4:53 pm
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