I’ve been collecting miles and reading your blog for about three years. Hawaii has been my dream trip. My wife and I have two kids, ages 11 and 14. We live in the Buffalo, NY, area.
Due to the long trip, I wanted to try first class (never flown it before). I researched best trips on Flyertalk and discovered that American Airlines, on 767 from Chicago or Dallas, seemed the best. Eleven months in advance I booked two first class and two coach tickets. I booked outbound and return separately as one ways. Total miles: 240K (75 first, 45 coach each).
For inter-island flights, I used Penfed points. Somehow, they were far cheaper than buying directly. For example, if the purchase price was $79, it was only asking for 4K points.
For hotels, we used five nights at Sheraton Maui (48K Starpoints, 12K per night with the fifth night free), four nights at Hilton Waikoloa Village, and one night at a bed and breakfast in Volcano (Expedia BRG). For the Hilton, I had booked a 145K point award. But then I read a post from Gary’s View From The Wing stating a Travelocity 20% American Express code with a 20% Amex Facebook. After both 20% discounts, I ended up getting the room for about $680 including two breakfasts per day. This was a tough decision, but I thought paying with cash was a better deal and canceled the reservation with points.
The trip has been fantastic. We all love Hawaii, the amazing sights, and the hotels we’ve stayed at. I’ve even used points from Capital One mile match to pay for car rentals, etc. Through American Express Platinum, we had lounge access for layovers and SPG Gold.
Things I’ve learned:
Invest time to keep checking prices and availability. The inter-island flights and car rentals changed frequently day to day. By being patient and persistent I saved a lot. Also, I wanted to get the other two long flights moved to first class. I checked multiple times every day leading up to the trip. No go on outbound, but two days before the return I scored two additional first class tickets.
First class on the long flights was amazing. How can we go back to coach?
I knew that hotels considered Priceline and Hotwire “inferior” bookings, but it seemed also to be true for Travelocity. Hilton would not even allow me to attach my HHonors gold number until check-in. Also Hilton.com does not have a low price guarantee, something I thought odd.
Thanks for all that I’ve learned from you.
Mile: Thanks for sharing your story, especially the part about determining that, in some instances, paying cash is actually the better option. If you feel your points are worth more than the cash required (with stacked 20% off coupons you made that choice easier), pay the cash. Those points and miles can be used at a later time for a higher value. I’ve done the same thing more than once when I found a better deal using cash and saving the points for a rainy day.
Glad you liked Hawaii!