*This will be an irregular series on some of the free (or almost free) trips I’ve booked. I’ve posted short summaries of these trips on this page but this series will go more in depth and I’ll breakdown how I booked this trip.

Andrea and I just got back from Maui on our 2nd Honeymoon and it was an absolute blast – the perfect balance between a nice relaxing vacation on the beach sprinkled in with some activities such as a rainforest hike to waterfalls and a canoe outrigger experience.  Fortunately points and miles made this 2nd Honeymoon a reality and in this post, I’m gonna breakdown exactly how I booked the trip with points and miles and how I acquired the points and miles needed for a trip like this.

Flights:

Departing: Hawaiian Airlines JFK-HNL-OGG for a cost of 17,500 miles plus $5 in taxes per person.
Return: Hawaiian Airlines OGG-HNL-JFK for a cost of 17,500 miles plus $5 in taxes per person.

Once I saw Hawaiian Airlines offered a direct flight from NY to Honolulu, I wanted to book this flight for our Hawaiian getaway to avoid stopping in LA or SF. There are two basically two main ways to acquire Hawaiian Airline miles – 1) Hawaiian Airlines credit card from Barclays or 2) Transferring American Express Membership Rewards points to Hawaiian Airlines.

Andrea and I decided to each open a Hawaiian Airlines credit card (though it was from Bank of America a year ago) as the credit card offered a signup bonus of 35,000 miles for spending $1,000 in three months. The annual fee of $79 was not waived. The minimum spend was pretty easy to accomplish based on our normal level of spending so it wasn’t long before we had 36,000 miles each (35,000 bonus miles + 1,000 miles for spending $1,000).

Hawaiian Airlines charges 40,000 miles roundtrip from the mainland US to Hawaii but as a cardholder, you were entitled to a 5,000 mile discount on award flights, reducing the cost per person to 35,000 miles plus $10 for taxes roundtrip! So for paying an annual fee of $79 each, we got our flights to Hawaii covered. Compared to the retail cost of these flights of about $1,000 each, we got a deal!

Hotels:

Grand Wailea (a Waldorf Astoria Resort) – 2 Nights

Grand Wailea

Back in early 2013, I applied for the Citi Hilton HHonors Reserve credit card which offered a signup bonus of 2 free weekend nights at ANY Hilton Hotel for spending $2,500 in 4 months . The annual fee of $95 was not waived. The Hilton family includes Conrad, Hilton, Hilton Garden Inn, Waldorf Astoria, etc. so to make sure I maximized the value of the free nights, I made sure to use them at a Conrad or Waldorf Astoria. Additionally, this credit card grants you Hilton Gold status which gives you free breakfast, room upgrades and other benefits when staying at Hilton Hotels. This is a HUGE perk!

With the flights booked to Maui, I booked our first two nights in Maui at the Grand Wailea. In addition to getting the nights for free, by using points we avoided the $25 daily resort fee, so our bill would have literally been $0.00 if we didn’t have a rental car which we had to pay for parking. Nights here can go for $300-$600 depending on the time of year, so we easily got $600-$1,200 in value.

Andaz Maui at Wailea

Andaz Maui

The Andaz Maui is a brand new hotel that opened in fall 2013 so of course I wanted to stay there on our trip. The Andaz Maui costs 22,000 points per night or you could use half the amount of points per night, 12,500, plus a co-pay of $150 per night. I opted to use 12,500 points + $150 per night but you could easily use all points to make the stay free. I did this because by paying a small co-pay per night, I could apply a suite upgrade certificate I received from opening the Hyatt credit card (more on this in a future post).

To acquire Hyatt points, I transferred points from my Chase Ultimate Rewards account. In the past I signed up for several Chase Ultimate Rewards cards, including the Chase Sapphire Preferred and the Chase Freedom. The beauty of Chase Ultimate Rewards points is they can transfer to many different airlines and hotels including United, Southwest, British Airways, Marriott, Hyatt etc. so you can use them as needed. I had over 150k Chase Ultimate Rewards points from signup bonuses, everyday spending and other small promotions so I transferred 75k Chase Ultimate Rewards points to Hyatt to book the stay.

My total cost was 75,000 Chase Ultimate Rewards points plus $900 which might seem steep until you consider this hotel routinely goes for almost $600 a night for a standard room and a $1,000 for a suite, which we stayed in! For 6 nights in our suite, it would have cost $6,000 (which I simply couldn’t afford) so paying $900 represents a pretty nice discount!!

From good flights on Hawaiian Airlines to a great stay at the Grand Wailea to an AMAZING stay at the new Andaz Maui at Wailea, Andrea and I can’t wait to return to Maui.

Remember, this can be you and I’d be happy to help you get there!