When my wife married me, she knew about my obsession with points and miles acquisition. Myunspecified plan to fund the honeymoon trip to Maui became clear when she saw we only had $175 budgeted for the trip’s hotel and airfare. Despite her knowing about the wild world of points, she still asked: How will we stay 6 nights in Maui for only $175??

Generally speaking, I had this strategy: she and I would each acquire two airline credit cards (each with a bonus equivalent to a one-way ticket); and 1-2 hotel cards incentivizing new cardholders with free nights. When deciding which cards to pursue, we considered which airlines best met our needs, and whether there were specific hotels in Maui that we particularly wished to stay at. For us, we were traveling from Seattle and it was important to us to stay at the Westin Maui Resort and Spa, Kaanapali for at least part of the trip.

With this in mind, we each obtained:

Card: Alaska Airlines Visa
Reward: 25,000 miles (good for a one-way ticket from Seattle to Maui)
Cost: $75.00 (annual fee)
Spend Requirements: NONE

Card: United MileagePlus Explorer Visa
Reward: 30,000 miles (good for a one-way return ticket from Maui to Seattle)
Cost: FREE (annual fee waived first year)
Spend Requirements: $1000 in the first 3 months

Card: The Hyatt Visa
Reward: 2 Free Nights at Hyatt Properties Worldwide
Cost: FREE (annual fee waived first year)
Spend Requirements: $1000 in the first 3 months

Card: The Starwood Preferred Guest (SPG) AMEX
Reward: 25,000 points
Cost: FREE (annual fee waived first year)
Spend Requirements: $1000 in the first 3 months

Because we each obtained these four cards, we were responsible for two $75 annual fees (Alaska VISA) and a total of $6,000 spending requirements within three months. However, when you’re planning for a wedding, placing deposits, buying a dress, the rings, etc.; this is a more manageable requirement and responsible in that you’re only spending money you planned on spending anyway from savings (if you haven’t saved a budget for your wedding, you’ll need to factor APR into cost/benefit analysis in the event you’re unable to make the payments in full).

Our rewards netted us two one-way departure tickets from Seattle to Maui on Alaska Airlines; two one-way return tickets from Maui to Seattle on United Airlines; two nights at the Westin Maui Resort and Spa, Kaanapali; and four nights at the Hyatt Regency Maui Resort and Spa, Kaanapali Beach all for $172.40 in fees (we paid a total of $22.40 in taxes on the airfare in addition to the two $75 annual fees). If we had opted to pay for this same trip without rewards, it would have cost us $3,430.00; a savings of 95% that let us use that money on dining out and other activities during the trip instead.

If we had opted to pay for this same trip without rewards, it would have cost us $3,430.00.

One note: Hyatt does not typically allow you to book your two free reward nights consecutively. But because we each had two nights, we booked them one at a time in an alternating fashion (i.e. my 1st night; her 1st night; my 2nd night; her 2nd night). Afterward, we called Hyatt with the four confirmation numbers and they were great about grouping them into a single reservation. We were a little worried they wouldn’t be happy with us when we arrived, but instead, the front desk staff welcomed us as Platinum members (a perk of being a cardmember for Hyatt), and upgraded us to the Honeymoon Suite for all four nights at no charge!

Some final tips: Prepare for this moment by having great credit, and a good payment history with your existing cards/banks. When it’s time to start applying, submit all of your applications in a single day. Banks will not often see new applications within a 24-hour period and you’ll have an easier time being approved for all four. Staggering your applications could risk you being declined towards the end of the process. After receiving each of your credit cards, make a date in your calendar to cancel them 8-11 months after you receive them to avoid future annual fees while also not getting flagged for scamming the award system with the card-issuer. However, if you’re like us you’ll keep the Hyatt VISA. With a free annual night awarded each anniversary, the $75.00 annual fee is more than reasonable. Additionally, you’ll carry Platinum status for any of your stays with them.

As others in the collecting-world have mentioned in their posts, this trip is just the beginning thanks to the opportunities presented by mile and point collecting. For instance, my wife is enjoying a free business class flight to Germany, and we’ll be visiting Cancun, Orange County and Orlando this year; all at a significantly reduced cost thanks to some recent promotions. This crazy hobby has transformed our lives and allowed us the luxury of travel without breaking the bank each year.