Travel bloggers share their first rewards ‘wins’

The world as seen by rewards bloggers can seem daunting to newcomers. While they’re jetting across the globe in business class and staying at posh hotels, you’re still wondering what to do with your handful of airline miles.

But everyone has to begin somewhere. We reached out to seven seasoned travel bloggers to find out about their very first rewards trips – and what they learned. While some leaped bravely into the world of the traveling elite, others got more humble starts.

Caroline Lupini, blogger at

PointPrincessHer first rewards win: Flights to Southeast Asia
After flying economy class to her destination, Lupini spent five weeks backpacking in Southeast Asia, sleeping in hostels for less than $5 per night. Her return trip was more glamourous – first class via Thai Airways and Lufthansa.

“Going from backpacking to flying first class is not an experience I can compare to many others in my life,” she says.

What she learned: Lupini needed to make some itinerary changes after booking. Problem was, United had just devaluated its rewards fares and didn’t want to allow the changes at the same mileage cost.

“Booking this award 100 percent taught me about persistence,” Lupini says.

After hours on the phone talking with United agents and supervisors, Lupini says she’d use a more efficient method today.

“One thing I would have done differently today is take the situation the social media route,” she says. “I find that many of the airlines and hotel programs are able to help quite a bit through Twitter while also making it entirely less frustrating.”

Scott Grimmer, founder of

Scott GrimmerHis first rewards win: Business class flights to Australia

Grimmer and his brother opened American Airlines cards (each getting sign-up bonuses of 150,000 miles).

“We used the miles to book a dream trip to Australia in business class to scuba dive the Great Barrier Reef, a dream of mine, and watch the Australian Open tennis tournament in person, a dream of his,” Grimmer says.

What he learned: Simply that success with miles and points is addicting. He’s since opened many credit cards while maintaining excellent credit.

“The rewards have allowed me to see nearly 60 countries and travel in business and first class whenever I’ve wanted,” Grimmer says.

Charles Barkowski, founder and author of Running with Miles

CBarkowskiHis first rewards win: Five nights in a Jamaican resort

Although he’d traveled with miles and points a few times prior, Barkowski considers his first big win to be the anniversary trip he took with his wife to Jamaica. It was a non-traditional booking; Barkowski used airline miles (in a now-defunct program) for a hotel reservation.

“That is really never a good thing to do, but at the time, Continental and their affiliate hotel programs were having a sale on various properties when you redeemed your miles for a hotel,” he says.

So, for 90,000 Continental miles, the couple got a five-night stay in a suite at the Grand Palladium, an all-inclusive resort in Montego Bay, Jamaica (a $2,600 value). US Airways off-peak rewards tickets (and a 5,000-mile discount for being a cardholder) got them there for 20,000 miles per person.

What he learned: By breaking conventional rewards rules, Barkowski says he learned to “consider looking outside the box of normal award redemptions.”

While 90,000 miles may have gotten them one-and-a-half coach tickets to Europe, “trading that for five nights in a secluded suite in an all-inclusive was incredible,” he says.

Howie Rappaport, editor at large for Frugal Travel Guy

His first rewards win: Flights for a destination wedding and honeymoon

HowieRappaportRappaport and his wife used rewards to fly from Boston to Savannah, Georgia, for their destination wedding and then on to St. Lucia for the honeymoon. The cost: 70,000 SkyMiles and just under $100 in taxes and fees. Rappaport already had 40,000 miles in his Delta frequent flier account and picked up the rest via a credit card sign-up bonus.

“We flew economy class on Delta Air Lines and had no real want to be in first,” Rappaport says.

What he learned: That first modest win involving a single credit card inspired Rappaport to explore bigger possibilities. He and his wife now pick up about a million points and miles per year through credit card sign-up bonuses and have their sights set on flying first and business class to the United Arab Emirates and Thailand.

Even so, “Thinking back to that first trip, I wouldn’t have changed a thing,” Rappaport says. “We got exactly what we wanted. Sure we didn’t know that we likely could have traveled in first class, but for a four-hour flight it was no big deal for us … we were honeymooning.”

Leslie Harvey, founder of family travel blog Trips with Tykes

Trips with tykesHer first rewards win: Business class flights to Spain

Harvey and her husband left their child with the grandparents for this adventure. The miles came from a combination of credit card sign-up bonuses and the standard business travel they were already doing.

“Being able to travel without a baby or toddler was luxurious enough, but traveling in an international premium cabin for the first time was nothing short of amazing,” Harvey says.

What she learned: Rewards, Harvey realized, could also be used for the entire family, with few changes.

“As a traveling family of four, we usually don’t redeem our rewards on luxury hotels or premium cabin air travel so we can stretch our points further,” Harvey says. “Occasionally, however, a higher-end redemption makes sense if it eases the pain of traveling with a baby or toddler by improving upon difficult trip logistics. Points enable our family to have the luxury of that choice.”

Another lesson learned: Persistence pays off.

“It took a lot of research to find the seats we wanted at the lowest-level award price,” Harvey says.

Laura and Lance Longwell, founders of Travel Addicts

Travel AddictsTheir first rewards win: Flights to San Francisco

The couple used airline miles to travel from New York City to San Francisco.

“We were living in New York City and didn’t have a lot of money to travel,” Lance says. “…We were thrilled to get free flights.”

What they learned: Over time, as the Longwells learned more about mile and point value, they learned their trip wasn’t the most judicious use of miles.

“Flights at the time were relatively cheap, and we would have been better off saving [our miles] for a more expensive flight,” Lance says.

These days, the Longwells look for ways to add personal vacations onto business trips, meaning their flights are subsidized and their rewards strategies center mainly on hotels.

“Travelers who are new to reward programs should figure out what they want and what their trip goals are, and then find the travel rewards programs that meet those goals,” Lance says.

Geoff Whitmore, blogger at NoobTraveler

Geoff WhitmoreHis first rewards win: Flights to Italy

Whitmore and his wife used airline miles several years ago to cover half of their airfare to Italy.

“It was our first trip to Europe, which had been a dream of ours,” he says. “We earned the miles from each of us signing up for the United rewards credit card, and couldn’t believe that we could actually use the miles in a tangible way.”

What he learned: Whitmore has since learned that he can do better than half a trip in economy. These days, first- and business-class international is the norm.

“Our first trip taught us that we could travel more frequently than we thought and for a price that we could afford,” Whitmore says. “In hindsight, I wish we would’ve jumped all in on rewards travel faster.”

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