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I was backpacking in Lisbon, Portugal, when I first read about The Points Guy’s million-mile photo contest and scavenger hunt. I knew instantly which travel photo to submit, and the scavenger hunt was organized in my former hometown of San Francisco. Within minutes, I had decided the million JetBlue TrueBlue points would be mine.
To recap how the competition played out: My first challenge was to get people to “like” my picture. I rallied all of my friends, and they rallied all of theirs. But I still needed more votes and a potential +1 if I was a finalist. My little sister, best friend and main travel and adventure buddy Karen, who is getting married next year, was the logical choice. The call was an easy sell:
“Want a free honeymoon?”
(Pauses “Games of Thrones” DVR)
“I’m sorry can you repeat that?”
With her additional “Help me win a free honeymoon!” appeal plastered across social media, we finally accrued enough votes to put us in the running. Our picture won over the judges and we became semifinalists. I had drifted into Morocco by the time I got the news, so I booked a one-way United Star Alliance award flight home to Chicago for 40k miles. It wasn’t the best value for UA miles (round trip awards offer many more perks), but I needed to get home! And the potential payoff would make it well worth it. I circumvented the close-in booking fee, and I worked in an overnight layover in Geneva to visit a new city and see one of my best travel friends. The airport is a quick 4-kilometer train ride into town, making Geneva a convenient, but expensive, choice for an overnight.
After two unforgettable days in San Francisco and running ourselves ragged in the scavenger hunt portion of the competition, Karen and I were JetBlue TrueBlue millionaires. I didn’t want to plan how I would spend the points before actually winning them, so I initially didn’t have an answer to everyone asking “What are you doing with the points?” But, now I’m finally ready to take these TrueBlue points and make it rain:
My first priority is sending Karen and her fiancé Mike on their honeymoon. They had already locked in Hawaii as their choice, and luckily JetBlue’s only airline redemption partner is Hawaiian Airlines. I offered to send them in first class, but Karen has adopted my philosophy on award travel: I’d rather fly somewhere twice in coach than once in first class. So, Karen and Mike get free flights to Hawaii, and they are applying for hotel credit cards for a free stay. I’ll also throw in a future anniversary trip to the Caribbean, where JetBlue has many more options.
Cost: 150,000-200,000 points
I Get High (as in Flying) with a Little Help from My Friends
The backing I received as I promoted my picture early on in the contest was a little overwhelming. Family, friends and even people I barely knew voted, shared and flooded their news feeds to get me the likes I needed. Since winning, I’ve gotten well over a million miles worth of “So where are you taking me?” And while no one actually expects anything in return, I’m giving something back to those who helped to get me there. I’ll have my very own unscientific and impossible-to-make-fair lottery where I’ll give one lucky supporter 50,000 points — potentially enough for two round-trip flights to the Caribbean! Thank you, everyone! And you’re welcome, one person!
Cost: 75,000 points because I’ll probably invite myself along.
Aruba, Jamaica, Ooh I Wanna Take Ya
I was supposed to be adventuring through Malta and Italy’s Amalfi Coast with my friend Claire on the weekend of the scavenger hunt, and she agreed to push back our trip a month to accommodate. To show my gratitude, we’ll go on another adventure to… Bermuda? Why not. It’s the only spot I haven’t explored from The Beach Boys’ song “Kokomo.” Thanks again, Claire, although I think you’re coming out ahead here.
Cost: 50,000 points and that song in my head for the rest of the day.
Team “Biros Bonuses”
Even a million points won’t cover an exotic vacation for all of my siblings and their families (27 people!), but Karen and I can at least thank our parents. Mom and Dad, as “bonus” children No. 5 and No. 6 (hence the scavenger hunt team name), even if we weren’t part of your original plan, we’re sure glad we’re here, and we want to make sure you are too. A long weekend in Savannah or Charleston will have enough history and Southern charm for dad, plenty of flowers for mom and a beach for us kids.
Cost: 100,000 points
Even after my spending spree, I’ll still have over half a million points in the bank. I’d make a terrible hotel chain heiress/socialite — bingeing isn’t my style. Instead, I’ll enjoy a steady Caribbean perma-tan for the next several years (Cuba is high on my list), and I may dabble just a bit in JetBlue Mint.
Featured image of Pink Sands beach in Bermuda courtesy of Shutterstock.