We live in Colorado as well and also travel to Maui 2x per year. I would suggest the following:


[*]Establish an Aeroplan (Air Canada account for you and your wife)[*]Each of you apply for the latest AMEX Platinum card which has a 50,000 Membership rewards bonus for $3K spend in 3 months. (100,000)[*]Each of you apply for the AMEX Gold card which has a 25,000 MR point bonus for $2K spend in 3 months. (50,000)

If successful with the above you can transfer AMEX MR points to Aeroplan which is a United partner via Star Alliance. Air Canada only requires 45,000 points per coach ticket from DEN-OGG on the same United flights.

Book 2 RT tickets for your self and another using Aeroplan (90,000 Points)
Book 2 One way for the other two family members using Aeroplan (45,000)
Book 2 One way for the return flight for two using the United points (60,000)

Each of you apply for the Hilton cards from:

• American Express 60,000 each (120,000)
• Citibank 50,000 each (100,000)
• Bank of America Virgin Card (up to 70,000 each) if you transfer to HHonors
• Bank of Hawaii Hawaiian Air (70,000 each)

This would be around 720,000 Hilton Honors points - good for 12 nights at the Grand Wailea or two rooms for 6 nights at the Grand Wailea.

Good Luck