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Christmas Family Vacation in Hawaii — Reader Success Story

Aug. 10, 2016
6 min read
Christmas Family Vacation in Hawaii — Reader Success Story
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One of the things I love most about being The Points Guy is getting to hear stories from readers about how award travel has affected their lives — the exotic vacations they’ve planned, the trips they’ve made to be with family and friends, the premium seats and suites they’ve experienced and so much more, all made possible by points and miles. I love to travel and explore, and it’s an honor to be able to help so many of you get where you want to go.

I like to share these success stories to help inspire you the way you inspire me! From time to time I pick one that catches my eye and post it for everybody to enjoy. If you're interested in sharing your own story, email it to; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. If we publish it, I’ll send you a gift to jump-start your next adventure!

Recently, I posted a success story from John, who booked a last-minute trip to see his favorite team play for the Stanley Cup. Today, I want to share a story from TPG reader Mara, who used points and miles to book a Christmas vacation to Hawaii with her whole family. Here's what she had to say:

Mara and her family spent a week at the Hilton Hawaiian Village resort on Waikiki Beach.

I've been a points and miles enthusiast for several years. My husband and I have enjoyed exploring the world together, but I recently decided to aim higher, and began planning a Hawaiian vacation for our entire family of 14. With grandchildren in school and other scheduling conflicts, we had to find a week that worked for all of us. Our oldest son suggested Christmas, and though I knew booking award travel during the holidays might be more challenging, I got to work exploring options!

My husband and I had gradually built up a bank of travel rewards, thanks mostly to credit card sign-up bonuses and the Daily Getaways deals. Aside from what we'd already spent on our own trips, we had accumulated extra Delta, American and United miles, a large stockpile of Hilton HHonors points, and other rewards from assorted programs like Southwest, Alaska and Wyndham. Our Hawaiian vacation took a lot of planning, but after piecing together awards with different points and miles, it paid off.

On Christmas Day, my husband, our oldest son and his family of five flew from St. Louis to Honolulu via Denver on United Airlines. I left from St. Louis with another son and his family of four on American Airlines. Our daughter's family of three flew from Nashville (also on American) to meet us in Dallas, and the eight of us then flew together to Honolulu. Incredibly, while our trips began in four separate groups on two different airlines, we all arrived in Honolulu within about 30 minutes! We used my Citi Prestige Card to visit lounges during layovers, and saved a lot on checked bags thanks to other cards.

My original plan was for all of us to stay at the Hilton Hawaiian Village using our Hilton Grand Vacation Club points. That was another challenge, since so many people who own weeks there also wanted to be there at that time. Fortunately, we were able to book a three-bedroom penthouse suite with magnificent views and amenities for six nights, and used our HHonors points at the nearby DoubleTree to cover the rest of our accommodations.

The return flights didn't fall in line as neatly as the outbound ones, but we made it work. We snagged three Delta awards for our daughter's family to return to Nashville on New Year's Day. Our oldest son took his family to visit one of the other islands (where they used our timeshare), and purchased tickets on United to fly home from there. Incidentally, they took a voluntary bump en route home and got enough in United vouchers to cover their flights to Alaska this summer! Our younger son and his family took Allegiant to Los Angeles to see Universal Studios, and then flew back to St. Louis using our Southwest Rapid Rewards.

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We had an awesome Christmas week in Honolulu, but my husband and I weren't done yet! We used Hawaiian Airlines miles for flights to Maui and a quiet extension to our trip. We spent three nights at the Days Inn Resort using our Wyndham points, and three more immersing ourselves in the luxury of the Grand Wailea. To cap it off, we flew home on Alaska Airlines, and scored a huge discount by using the Alaska Airlines Visa companion fare.

Our trip wasn't the most efficient use of points and miles — it was prime vacation time, so we had to book some awards at the standard level. Ultimately, we were able to get all our families to Hawaii for a week, and only spent about $2,500 out of pocket. Could we have afforded to go if we had to pay for everything? No! Was it worth the effort? Absolutely, positively, yes!

Booking awards for a large group comes with challenges you probably won't encounter when traveling alone or as a couple. You might not have enough points to book everyone on the same flight or at the same hotel. Even if you do, you may have trouble finding award availability, since many travel providers limit the amount of space allotted to award bookings.

As Mara's story illustrates, flexibility is the key. By traveling on holidays and splitting the group as needed, her family was able to take a memorable trip together in a popular destination. While there weren't enough saver-level awards for everyone, Mara helped their cause by planning far in advance and being willing to travel during off-peak times. A similar trip probably could have been had for less, but it could easily have cost a lot more. For more suggestions about traveling in a group, check out Jason Steele's list of Tips for Booking Family Award Travel.

Mara and her husband Rudy snapped this picture of their favorite sunset during the trip.

I love this story and I want to hear more like it! To thank Mara for sharing her experience (and for allowing me to post it online), I’m sending her a $200 Visa gift card to enjoy on future travels (purchased from Office Depot with my Chase Ink Plus, of course), and I’d like to do the same for you.

Again, if the strategies you’ve learned here have helped you fly in first class, score an amazing suite, reach a far-flung destination or even just save a few dollars, please indulge me and the whole TPG team by emailing us with your own success stories (see instructions above). You’ll have our utmost appreciation, along with some extra spending money for your next trip.

Safe and happy travels to all, and I look forward to hearing from you!

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